I figure a break from one of my “versus style” blog titles would be a new way to kick off the new year. To recap, my mother still has cancer, she has been in a hospital or rehab facility for other a month, and I haven’t seen her in over 2 weeks due to Covid-19 lockdowns. She herself tested positive for Covid, but since she is vaccinated her symptoms were mild, and she tested negative recently. And the slow motion eviction hearings continue to trudge along. Let’s move along.

New years are times for resolutions, which I never do. But in the spirit of a topic which matches the purpose of this blog, as well as to re-evaluate where I stand on things, I thought it was time to look at my own personal “don’t” list. As a nearly forty year old virgin who has only been on three dates and never kissed anyone, I would be dishonest if I didn’t admit to a bit of desperation. That’s evident in journal entries where I state, and justify at length, a willingness to date less-than-perfect (or even decent) women. This doesn’t speak entirely highly of me, at least in that I boldly proclaim I am not a moral paragon in everything, but I feel it is honest.

But at the same time, my view on other related topics has changed…or, as a politician would say, “evolved.” When I began this blog back in 2014 (geez), I was avidly against seeking out a sex worker as a viable option. It was suggested to me more than once but I usually help firm. But as my thirties have crept on, my stance on that has changed. Currently I am not morally or spiritually opposed to it as a choice; I simply insist that it be done somewhere legal (i.e. Las Vegas) and at a time when I have more freedom with cash (i.e. no risk of eviction) and I no longer have to worry about spreading a deadly pathogen (Covid-19 is dealt with). I like to tell myself that this is because my own views on sex work have changed, but in reality it may simply be self serving. I am officially in “circus freak” territory, and paying for it may very well be the only way I will ever lose my virginity, so this mental shift is convenient. Unlike many men, I can admit at times when I am full of crap.

What are my views on other moral or legal lines in the sand in regards to sex? After all, many men are pretty mercenary about it — especially those with many partners. And more than a few older male virgins I have read postings of feel entitled or justified with doing almost whatever it takes. I claim I’m not, but I’ve also admitted to being less than a knight’s templar about it. I’ve acknowledged various limits on my own quest and zeal to finally shed the mask of the Dateless-Man and be a normal (or more normal) person here and there, but I may as well officially examine it.

Plus, it leads to a list, and lists are fun to read.


1). I Will Not Physically or Verbally Assault Someone

Let’s get the obvious and most horrible and criminal thing out of the way. I doubt any man goes online and avidly admits to wanting to be a date rapist, but a lot of “incel” or “MAGA” posters get pretty close. This includes “negging” or other verbal attempts to belittle or shame a woman into it, even if I have no idea how that works. This is wrong and I think far more men out there are guilty of this than anyone will know. Virtually every woman I have ever known, either as a relative or friend, who trusted me enough to be vulnerable about her past, has admitted an incident where a man either molested, assaulted, or raped her, or attempted to. Every time it happens my heart sinks; a part of my soul whispers, “Not you, too.”

2). I Will Not Get A Woman Drunk

Pretty closely associated to the first one, but the subject of so much hand wringing by a lot of men (and some conservative women). I’ve mentioned it in a few articles but years ago when I used to frequent cyber cafes, I wound up meeting a man (and I use the term loosely) who was all but a self admitted date rapist. However, his tool was alcohol; he bragged about going to other countries during major holidays and taking advantage of wasted women. I was disgusted and called him “a date rapist” to his face more than once. But he was only the bluntest and sleaziest example. A part of me wonders how many of my own friends and associates perhaps took advantage of this at least once.

Now, this is not to say I am the reincarnation of Elliot Ness eager to take an axe to any keg I see. I am not an anti-alcohol zealot (even if I have seen the woe that alcoholism brings many times, especially within my own family or when my mother dated). I don’t personally drink outside of social settings, and even there, I drink to excess very rarely. I do so rarely that my friends speak of those occasions as akin to the times they saw Bigfoot (or as one used to put it, “the bug up your ass slipped out”). I don’t even drink to get buzzed. I would not shame or belittle a woman who drinks in my presence or on a date.

But I would pay attention if she does so to an extreme. If her speech is slurring, her eyes are glazing and her stance is wobbling. If I even suspect her inhibitions are gone, then I will refuse any sort of sexual activity; even if she is eager or over eager. My philosophy is that it is not right to take advantage of someone who is chemically vulnerable, no matter how desperate or lonely I am. And in theory, if she likes me enough to flirt when she’s drunk, I can wait until she is sober to avoid any risk of actions we regret. One of few advantages to being an older virgin is patience. I’ve spent decades in romantic futility. Allowing a night or two to pass to see if she still wants to jump me after the hangover has passed will not break me.

It hasn’t happened often, though, despite most of my friends (of both genders and even orientations) frequenting bars and clubs, or private drinking parties, avidly during their late teens into early 30’s. I’m too lame to be handsome even with beer goggles, apparently. But that’s a good thing as having to resist such efforts is not fun.

See also: Getting a Woman High/Stoned/Tripped Out. Since I do not engage in any such drugs, nor ever have, it’s almost a non sequitur.

3). I Will Not Lie

A part of me wonders if a large chunk of the reason why I was chaste during my high school and college years was because I often did my best to act like a tougher and more experienced person than I was. Since I was shy, I tried to project that I was so aloof and mysterious that it didn’t matter. And once I was old enough where romantic inexperience (of any kind, not just sex) was a subject of ridicule (i.e. puberty and early adulthood), I literally “made up” an ex. It would claim to have had an elementary school sweetheart. How long our romance lasted depended on how old I was. I’d mostly quit doing that by the time I was about 19-20, but by then the damage could have been done. I’d literally rehearse stories about her to the detail so I was never thrown off or missed details. If only I’d concentrated on being more self aware and presenting my best self, I may have gotten laid. But how many people who are in high school and college know who they are yet or are that fully self aware? I tried to be, but clearly wasn’t.

Many people are liars; many men are liars especially. We do it to cover vulnerabilities and/or get ahead. And if you’re in the “older male virgin community” (which doesn’t come with any perks or even parking validation), a frequent line of advice is to lie your butt off about your lack of experience. “Fake it ’till you make it” is a less blunt way of putting it. If you’re not charismatic or confident, pretend to be or act like it. And I’ve no doubt that it works for many people. Some could say the line between acting and lying is quality and skill. And I will concede there is a difference between lying and trying to act as someone you want to be, or aspire to be. “I’m not lying, I am pretending to be the confident person I’ve always wanted to be; I am just not waiting until it happens,” many a dating guru has claimed.

My problem is that it always rings hollow to me; always seems wrong. My heart is not fully into it, and never was even when I was younger and would literally rehearse it. And without that genuine passion, it falls flat. Plus, it is wrong to flat out trick someone into thinking you are what you’re not. This uneasiness extends to me being unwilling to put my best foot forward because I fear projecting a better image of myself than I know is accurate, but the line between lying and embodying my own poor self image is pretty fine.

So to keep this simple, by lying I mean flat out lying about previous experiences, or jobs, or identities, to try to impress someone. Lying about my job, my finances, my lifestyle, my romantic history, etc. I will not do this. It was so exhausting to do a half-assed version as a youth, and I do not miss the energy it took.

One dilemma, especially when it comes to dating, is where to draw the line between not lying and not being overly honest to a fault. Omission is not the same as lying. An omission is not telling a woman I am a virgin. A lie is saying or implying I have had sex, or previous relationships, or an ex somewhere, or am a doctor, and so on. We all omit things in our daily lives and naturally our love lives, and that is okay and even necessary. But lying? No wonder lawyers and financial types make out like they do.

While few if any women grill people about their sex lives in older adulthood (as opposed to our youth, when peer pressure fuels it), natural organic conversations during the exploratory phase can lead to certain compromising questions. For example, while it is true that most women don’t want to know details about a man’s sexual history, people dating in their 30’s and 40’s may casually ask or inquire about any children. And while I will not lie, certainly a man who is pushing forty who has no children, is not divorced, and has never married is going to elicit further questions. And most people are not terribly open minded or nonjudgmental.

“It just never happened because I was painfully shy and had to spend a lot of my spare time tending to a disabled mother, a dying grandmother, economic problems and then an eviction trial and here I am,” is not the sort of answer most women expect to those questions. A part of me wonders if that is any better than, “Because I am a bum who won’t commit,” because at least a bum can hit a G-spot sometimes.

One tactic is to try to deploy some old time manners and give an answer akin to, “A gentleman never tells,” or some variation. Back in the old days, an older single guy who may have been a virgin for all anyone knew was merely referred to as “a bachelor” (whereas a woman was “frigid” or “prudish,” or “an old maid,” which was horrible). My only problem is that I feel that is akin to when a witness under oath claims “I cannot recall” or a child says, “the dog ate my homework.” It only works on someone who is either very naive or a flat out moron. No man in the history of world events has ever failed to at least acknowledge a previous romantic experience if given half the opportunity. Not one. Ever. I’m sure the Pope somewhere chuckles with some of his deacons and bishops about that cutie who winked at him as he gave communion somewhere.

I suppose I could try to pull a Bill Bixby and try to pull off some line like, “Any time I spend with a woman, whether an hour or a lifetime, is a world that is ours alone together that I do not share without permission,” but c’mon, if I were that smooth I wouldn’t be in this position.

There ways ways to avoid lying while also not answering inconvenient questions. A sense of humor is key, even if that sometimes delays things (“I’m an enigma wrapped in a mystery contained within baloney”). Another is to be very specific. For example, if I said, “I haven’t dated in a while,” is not a lie. It is absolutely true. It only becomes a lie if “a while” is mutually defined as “within the last 7 years.” A lie would be, “I haven’t had a relationship in a while” or “I haven’t had sex in a while” (since no one would ever define “never” as “a while”).

Finally, there is always a simple, “I’d rather not talk about that,” if certain questions near the bullseye too closely. That can elicit a negative or more suspicious response, but it’s not a lie, at least. I feel no relationship, whether for casual sex or more can stand on a foundation of lies. I suppose my biggest problem is I consider a statement like, “I’m a cool and appealing man,” to be a lie.

4). I Will Not Sleep With Someone Who Is Physically Or Intellectually Unattractive To Me

Physical attraction is very subjective and I’ve always struggled to describe “my type” beyond generalities. I feel I am pretty flexible. At the same time I am not just “trolling for hotties,” especially since I am not one, and am capable of being attracted to someone I “click” with on a personal or intellectual basis even if she may not be “my type” physically. I once had a female friend who I’d met in an “anime club” in high school who remained friends with me through college. She was not my type physically but we got along well, had the same interests and had a ton of fun together. If she had been romantically interested in me, I’d have followed suit with full gusto. I’d have been happy if she’d been my first. I still regret not defending her more vigorously to some of my male friends who usually called her “ugly.” The most I uttered was an “oh, c’mon.” I sucked as a teenager.

I cannot become aroused to have sex with someone who does not check either one of those boxes. Like virtually every person, I would be willing to compromise for someone who was my type physically, with a bad personality. But I would also be willing to explore romance with someone who could engage my mind, fill my life with great dialogue and activity, even if she was not my physical type. But a woman who has neither, even if willing, I cannot compromise with.

I learned this a few years ago with an older friend of my mother’s. I chronicled this before but to keep it short, my mother had a friend from her working days who made in abundantly clear in often awkward and creepy ways that I was her fetish (“younger white men”) and she’d probably sleep with me if given half the chance. She was not my type physically, and while I’d had many conversations with her over a few years when she would visit my mother or go to dinners with us on occasion, I always found her personality to be abrasive at best and creepy at worst. Trust me, it was not easy coming to this revelation. I am sure a few of my male friends would have said, “Dude, you’re a virgin, just jump the old broad and get it over with.” In fact, one thing I was reeducated about from last summer’s BBQ was that a few of the men who rack up “high numbers” of “sexual conquests” do so in part because they accept any willing partner, regardless of personal taste. That isn’t me.

5). I Will Not Take Advantage Of A Fragile Emotional State

This is something I have definitely encountered a handful of times; more so than drunken come-ons. A woman who comes to me in a situation where she is seeking aid, especially regarding affairs of the heart, is off limits. Such things are things friends do for each other, and in my experience no woman who essentially asks someone they see as a friend for a shoulder to cry on or help to a problem is looking for an answer that ends with, “Date me.”

That’s not to say that I can’t date someone who has been through a break up or divorce or some trauma ever. But the time and place for that is not the initial seeking of platonic aid. At best you wait until the tears are dry and someone has recovered and in a better place before making an overture. I’ve never had the chance for the second part (since I’d argue a lot of guys love capitalizing on emotionally vulnerable women), but that’s life.

6). I Will Not Take Advantage of Extreme Naivete

I consider myself an open minded person who is not looking for an unrealistically perfect lover. Just because I graduated college does not mean I look down on someone who does not. And just because I sometimes use large, fancy words like a pompous robot doesn’t mean I look down on someone who does not. Nor would I be opposed to dating someone who was herself inexperienced.

But if I sense that someone is, to put it nicely, extremely naive (and to put it cruelly, is a blithering idiot), that is a turn off. Count it as having an “incompatible personality.” I actually am not looking for “a pretty bubblehead,” and I would become very uncomfortable around one, because I would feel as if she was being as bedazzled by my baloney as a deer in the headlights. For a lot of people, a whiff of imagination or a hint of intelligence from someone new in their life almost seems like magic. But I am not a magician nor do I want to unintentionally trick someone into thinking I am. I can imagine it would be very frustrating to meet a woman who was my type physically and was even nice enough, but was otherwise so vapid that it was like talking to an overgrown child.

This is a problem because a notable cohort of women who might date me are those who literally do not know any better. Such an concept feels wrong to me, as if I was taking advantage. Not that I am the smartest guy ever (since I can’t even talk to women romantically), but I don’t think I am the most naive, either.

7). I Will Not Beg or Badger

Some men are genuinely looking for “a pity lay” and will try to guilt a woman as a last resort. This is another thing which may be common in my “community” of unicorn watchers. And for a while I think I was one of them. But I am not anymore. I would feel extremely uncomfortable if a woman saw me as some sort of “intercourse charity case,” as if sleeping with me would allow her to file a W-69S form with her accountant somewhere. This is how my own behavior comes into play. If I sensed a rejection coming I would not go the opposite route of force, which is to beg, whine, and plead. Not only is it bad for the women, it is humiliating to me, and I’ve been humiliated enough in my life.

I suppose if a women did take pity on me and was not obvious about it and this was some genuine reaction to meeting me, that is one thing. But it would be another for me to beg, “C’mon, baby, I’m a real life 40 year old virgin and my mom has cancer. Can’t you do a fella a solid?” or some garbage like that as she rolls her eyes until she sighs and says, “Fine!” That is not romantic and it is not really satisfying for anyone.

8). I Will Not Bribe

Not the same as seeing a sex worker. A session with a sex worker is a mutually agreed upon business transaction; the business is simply getting laid. Bribery would be offering a woman who was not in that line of work or situation money or some good or service she wants to get sex. I am not the guy who would trade concert tickets for a blow job, essentially. And while I have rarely been in such positions, there were times I had access to spare press pass to a comic convention where, were I sleazebag, I could have tried to milk that.

And while I have never achieved any middle management or supervisory position in any job I have ever had (which, as someone who is pushing forty, is also underwhelming), were I do to so, obviously, I would not use it as a wedge to score sexual favors. There are plenty of men out there who do and it is only in the recent years of the #MeToo movement where some of this has been exposed.

9). I Will Not Sleep With Someone Who Is Involved With Someone Else

Note that this does not involve polyamory (i.e. someone who is in an open relationship where both partners have carte blanche to date others). Even though, if I am honest, I would probably be a little uncomfortable with that, too. But what I mean is that I will not date or have any romantic relations with someone who I already know is in a committed, monogamous relationship. I will not help someone cheat on their partner, no matter how desperate they are.

There has only been one time in my life where something close to this happened to me, and even to this day I am not 100% certain if it really was that. About 6-7 years ago on Facebook (give or take), a woman who was a loose acquaintance of mine (i.e. a friend of a friend from high school, at best) started to “instant message” me out of the blue. We had commented and reacted to each other’s statuses here and there and so we were not complete strangers. But out of the blue she started asking me if I was available to head to her house on some random night because she was lonely. I think the term she used was, “for some fun.” I knew her to be a married woman with kids, who at one point made a big deal of staging some high school reunion boat party. At the same time, I wasn’t sure if I was misjudging the situation and she could have just meant some kind of random platonic chill session. I did share the messages to another pal of mine who seemed convinced she was hitting on me; but then again, he does have Asperger’s syndrome. A few years later, via her Facebook statuses, she would announce that her marriage had been abusive, and she was currently divorced. And no, she doesn’t chat with me anymore. She rarely had to begin with.

Obviously I am not omnipotent and there is no way to know if a woman I am ever with isn’t secretly married or dating someone else and just using me for some sort of jealousy gambit or so forth. But I’m not willing to be “the other man” in a situation where I do know such things, is what I am stating. Again, this seems like an obvious thing, but I have known more than one guy in my social circle who simply didn’t care about boundaries such as this.

10). I Will Not Sleep With Someone “Barely Legal” Or Close To It

A lot of men out there, especially late bloomers, often seek to “make up for lost time” by trying to literally hook up with the types of teenage girls they couldn’t land in high school. The problem is the power dynamics are unbalanced and those can lead to sick situations. Women that young have not fully developed and are far easier to manipulate, which is predatory for the men who go after them. I do not mean men who go after minors; that is pedophilia and is thus a crime. I mean dudes who are in their 30’s or 40’s plus and go after 18 year olds, or close to it. While not a crime, it is gross.

There’s a loose rule regarding dating people younger which goes something like “half your age plus eight”. There are variations but the gist is that it gives a fair idea of a limit where things don’t seem so creepy. For me that would be someone aged 27-28, which still feels pretty darn young, but at the same time, a woman in her late 20’s is hardly a child or fresh out of high school or college. At one of my old jobs I had a co-worker in his early 40’s who used to brag about dating a woman who was half his age, and it was kind of gross. On the other hand, he also used to complain that she was “high maintenance” and wore him out, so maybe he got some of what he deserved.

The closest I got to this was chronicled in my early Kink Panther entries. To summarize, a woman from Spain private messaged me at random at another forum I post at and wanted to do text based role plays centered around the shared fetish of the message board. She claimed she was over 18, but I kept our role plays at a PG level because I knew she was young, and despite her best efforts to flirt with me online. She was easily impressed by my wordplay and imagination, but of course she was; she was a kid. Once she revealed she was under 18, I politely severed contact. I could easily see why some older dudes in my situation go after younger women; they can be far easier to impress due to inexperience. But to me, it made me feel uncomfortable and older than I was. I felt like Dorian Gray. One of the last Speed Dating events I did was at a 2015 comic convention, where a slew of the women were barely a day over 21, and I often felt like a vampire trying to talk to them. I prefer women my own age, or closer to it.


I am not trying to be a knight or samurai, only able to date under the strictest rules of engagement. And at the same time, I am aware that I am only human and prone to temptation. There have been times I have been tempted to cross a few of the above lines, and either I resisted or circumstances played out oppositely. I often feel guilt for being tempted, because I feel I know better and am not experiencing the hormonal shifts of puberty any longer, so I have no excuse.

I’d just to date someone and ultimately sleep with them without it being some manipulation or con job, and where I am able to satisfy and please something inside of them, too. I’ve never had sex before obviously, but what I at least want to imagine for it is that it is not a one way street and I would like to pleasure someone else. I think a lot of the “late bloomers” who eventually find sex, but not the boost in confidence they expected, experience this because they only focused on what the session did for them. They didn’t focus or find as much joy in what they did for someone else. I know one of my friends found confidence after he lost his virginity because he “knew he could please a woman.” Perhaps that is why for some, a sex worker isn’t satisfying — there is no way to tell if they are really “pleasing” her or if she is just being polite and professional (as only the most low brow prostitute would yawn or belittle her client). As much as I would like to touch and feel a real life woman in an amorous way, I’d also like to be able to scratch her itch, too. I’m not saying I want to be Don Juan, but I’d settle for being a half decent midnight snack. I’m not just looking to beat her in a round of FORNAL KOMBAT with a SEXALITY and then go to sleep.

But maybe my views of sex and the limitations I place on myself towards getting it are those of a idealized child who never did learn how to deal with the world of adults in this respect. Maybe one does have to be mercenary or opportunistic in order to get laid, at least sometimes or in the beginning. And maybe for a near 40 year old virgin, I am being too picky or specific. Maybe life is short and I should examine my options.

I don’t think I would ever be someone who sought sex at all costs. I never have been and I doubt I ever will be. I would rather die a virgin than ever feel that a woman has felt regret or disgust in being with me. There is more to life than sex; it just makes life more exciting, is all.

Thanks for reading.

I remain…the Dateless-Man.

Dateless-Man vs. Virgin Reddit, An Essay & a Bad Year

It’s time for the end-of-year wrap up. These usually used to be the least viewed out of all my bloggings out of a year, but that could have been because a few of them were just summaries of older postings. Or seeing my versus title against a year is a bit boring of a headline. Regardless, while there will be some updates or summaries of things, I have some new stuff to get off my chest about some related internet wanderings.

So, for the second year in a row I ask the universe, is this a lost year which wasn’t my fault, for once? The Covid-19 pandemic has stretched on for another year, due to several mutations as well as the blundering of the previous administration (and the fact that much of the third world is still acting as an incubator because rich men who own drug companies are greedy). This has limited dating options since many of us are nervous about gathering in public, and many outdoor activities or locations, such as restaurants, bars, clubs, concerts, and so on are closed or under reduced hours or have space limitations. Infections are on the rise in NY and lockdowns may be happening again soon. I just got my Moderna booster shot, at least, but with my mother even sicker than ever, dating certainly will be on the backburner for some time.

As if the pandemic wasn’t enough, my mother went to the hospital and was diagnosed with pancreatic cancer this fall. She’s survived major surgery (the Whipple Procedure), but her recovery has been very slow and fraught with having to navigate the haphazard, greedy, and often incompetent American health care center. Seriously, considering all of the medical mistakes we have seen, it is a miracle anyone goes to the hospital and survives any in-patient procedure. My entire life beyond work has been visiting her at the hospital or rehab center, buying stuff to bring to her, fretting about stuff to bring her, or recovering from it. Today, the rehab center/nursing home entered Covid lockdown because, according to the security guard, 5-9 people tested positive for Covid-19. At least 20% (or one out of five) of all of the people in New York who died of Covid-19 since March 2020 were from nursing homes, so they have zero tolerance. So that is something more to be anxious about.

For normal people, having their dating lives yanked from them by circumstances beyond their control such as a pandemic or family cancer or rampaging mimes would be bad enough. But for most of them, they could take some solace in the fact that they go to sow their wild oats, have wild times, and can linger on those fond memories of times gone back. All I have are missed opportunities or a lack of them. While I won’t blame 100% of my dating woes on one family crisis after the next, their impact on my lack of a love life has been background radiation and contributed. By the time I was a junior in high school, my mother became handicapped (both physically and legally). By the time I was a sophomore in college, my grandmother fell and from there I had to help mother tend to her. Grandma died in 2010, but mother has gotten steadily worse and worse. Throw in a slow moving and never ending eviction procedure which is now entering its third-and-a-half year, and there are a lot of “distractions” to deal with. And next year I will turn forty, and officially become a subject of mockery due to a Judd Apatow film.

Is it any wonder that the only place I can get laid or satisfy my lust is within my own mind? I suppose the only positive about 2021 has been my full embrace of acting out some of my fantasies and fetishes via online fiction and/or some text role-playing. Actually, my Deviantart online kink-writing has been going fairly well, I must say. Within roughly eight months I have written 20 pieces of fetish fiction (and reposted 3 from my older message board days that I’d dug up as filler). They are essentially fan-works featuring fictional characters owned by other franchises. I’ve got 88 “watchers” (akin to subscribers), 3,800 profile views, and my stories range between 2,000-11,000 views each. 99% of my readers (or at least watchers and commenters) are male (at least), but it has been very encouraging. As someone whose love life has essentially died before it began, it is comforting to know I have some kind of kinky imagination and a way with wording it. I am still not ready to admit what my kink is, though. It isn’t that horrendous or shameful on the surface, but taken alongside me being a dateless virgin, it makes me look less sympathetic. Few people have understanding for older male virgins considering how overrepresented we are in the realm of spree killers; any who are less than pure as the virgin snow are seen as creeps.

So for now I continue to split my online self into three forms. My everyday social media identity on Facebook, my identity as the Dateless-Man which I use to gripe about being single via blogs and message boards, and my other identity where I write fetish fiction and commiserate with other fetish fans. Call me Three-Face. I decide the fate of my victims by rolling a six sided die and applying simple division. There is a part of me which wants to be done with the masks and just face the world in all of my lonely, single, disgusting and kinky self, especially since 2021 has taught me that life is short (and usually awful). But then sanity, or my reliance on burying parts of myself which cause me anxiety, prevails.

For some purer fare, I did type out my idea of an ideal first date a few weeks after Valentine’s Day. It was a fun thought experiment. Ultimately I am not looking for a sugar momma, a super model, a surrogate mother, or even a sex goddess. I just want to find a compatible yet quirky woman who actually returns my affection for her and is either patient or adventurous enough to give me a chance. And has a cat, because I like cats. But so far, my only chance at any of that is within my own imagination and dreams. That is literally how I know I am dreaming, many times. I realize I am experiencing success with a woman, and know consciously this has never happened, nor could it. Then I wake up, usually five minutes before my alarm, and decide to lay there in hapless futility rather than urinate a little sooner.

Now let’s end the year on some NEW RANTS.

I am the sort of person who occasionally does online searches involving the community I have found myself a part of — older male virgins. And sometimes these searches lead me to strange places which make me feel things. Remember, as a man, I routinely bury emotions in order to slog through my existence, so sometimes I have to use triggers to deal with them, kind of like psychic ingrown toenails. And I found this Vice article about a section of one of the festering holes of the Internet, Reddit. Only one step above 4chan, it’s essentially the pipe just above the sewer canal. This section is called “the Virginity Exchange” which began in 2015 (a year after I started blogging here). In theory it was intended for older male virgins to interact with older female virgins and solve their problems mutually. In practice, it’s become a spot where virgins over 21 type up little life stories about their plights and solicit well wishes and encouragement from their fellow virgins in arms — and occasionally exchange private messages with women willing to “end their drought” as it were. To a degree it has probably replaced the Craigslist Personals section, which often filled a similar niche. There have been men who have finally “popped their corks” from the section with women who were not virgins but willing to sleep with one for various reasons. The forum rules are strict about many things, including no money changing hands. It’s since gone private over the past few weeks, but I read quite a few profiles by people who were mostly younger than me. While there are certainly older female virgins, it seems men are more likely to commiserate about it online; probably because they won’t get flooded with horny solicitations like if a woman did it.

I feel there is something here; I can certainly attest to feeling lonely and isolated regarding my state. It would be nice to be able to talk about it with others without feeling embarrassed or ashamed. The flaw is the devolution into being an online clipboard for desperate personals; while that is well and good for consenting adults, I think men have too few options with talking to people, or they are too ashamed to bring it up with people they know. I know I find it difficult to even approach this subject with the few friends of mine who do know. Maybe an evolution of this would be a MeetUp? Perhaps with an option to wear a kind of mask and not have to give a real name, like a Virgins Anonymous? Ideally I’d like it to be unisex, but I imagine if it were, the risk of all the dudes crowding around the one or two women might be too great. And get too many lonely men in a room together and a place to vent can quickly turn into a He-Man Woman-Haters club.

I’d like to not have to run such a thing, since to coin an old catchphrase, I am not only the president, I am also a client. But unless a moderator has the right attitude or credentials, it could easily turn into an “incel” recruitment seminar. It is odd how my mind always goes to some option where I can’t just find acceptance, I have to become the Grand Marshall Of The Virgins. Maybe it is because since I see no end to my own suffering, that the only way it can have a purpose is to be used to end someone else’s. That is the only good outcome of suffering; as motivation to help others suffer less, because one learns suffering is painful to endure. That and I feel I have something in me which could manage, yet I am not berserk enough to lead people astray. Yet in leadership is also an isolation.

I also happened across an essay written by Hogan Torah for Age of Empathy about his childhood friend who eventually became a 43 year old virgin. Hogan goes all the way back to the beginning talking about his pal Simon, who is a lifelong pal who became the drummer of their childhood band. As time went on, they all discovered girls, dated, and got laid, but Simon never did. He grew more awkward and bitter as time went on. Hogan and his pals often tried to “set their pal up,” usually with sex workers, but they always ended in disaster and proved to be counter-productive. Three years ago Simon grew frustrated by their obsession with his lack of a sex life and severed all ties. Hogan’s essay was part plea, part apology.

This piece struck a chord in me, and not only because it was kind of raw and was about a virgin who is less than 4 years my senior. It was because that it was an essay that could have been written by one of my own childhood and/or high school friends, albeit with many details changed. I never displayed outright hostility or bitterness to women like Simon did. My one and only time touching breasts was when I caught one of my friend’s girlfriends as she was about to faceplant on a porch after getting wasted; Simon essentially groped someone’s sister under the pretense of a massage. While none of my friends ever tried to sic a sex worker on me, they did do group trips to Las Vegas on at least 2-3 occasions before they all settled down with long term wives/lovers when they were in their late 20’s and early 30’s. I never went with them, usually under the very genuine pretense that I could not spare the 1-2 grand necessary to do so. But I also feared a situation as to what Simon experienced, where my “ever helpful pals” would “hire” a prostitute and then offer laughs and high fives as they all but personally witnessed me “lose my cherry.” And considering their closest attempt at this was having an in-joke about my status on Facebook around 2013, I would have definitely been suspicious of any effort by them to aid me. Even though they never did. The best that happened is on two occasions, one or two of my pals claimed they knew a single woman they thought was my type, and then zero came of it.

A part of me wonders if at least one of my friends see me as Hogan sees Simon; as some poor, beloved, tormented soul they failed to save from himself. And as much as I like to paint them as insensitive male brutes about this topic, I did myself no favors. I never officially asked for help, because I was too ashamed. I never even tried flirting with anyone or revealed I liked any women to them, fearing I would be derided (as I often derided some of them and I didn’t want to swallow my own medicine). I was uncomfortable at bars and clubs and rarely accompanied them there. They used to try to throw me birthday bashes at such places, and I always saw them as chores to attend. They’ve long since stopped doing that, and now I miss the attention; go figure. I never asked them for advice or if they knew anyone single. Then again, none of my friends, even those who are women, ever “recommended” me to some single pal or relative they knew. My entire network has known me as single since the day they met me and forever after, yet not once in their lives did they ever consider recommending me to a single person they knew of on their own volition. It could be a sign that people need clear pleas for aid; or that I am just that flawed a person that even my dearest friends could not imagine me as a sexual, potentially romantic figure for anyone. That all I ever was to them is a geeky mascot; a sexless cartoon character good for a laugh. And as much of a blast as it is to be a cartoon mascot, it doesn’t keep you warm at night.

Or even worse; the idea that among my group, I was “the Load” or “the Zeppo” (see Buffy the Vampire Slayer). That one person within every group who is the lowest among them; the least experienced and/or useful. The one who is in the background making sandwiches while the rest of the cast get their time in the sun. In fiction, these characters occasionally get their time in the sun and their fans (like Xander or Sokka). In real life, we just fade into the Internet.

What are my goals for 2022? Avoiding getting fired, or evicted, and trying to keep my mother alive. Same as usual. With the dreaded inevitability of me becoming a forty year old virgin, I have flirted with the idea of trying to garner more online attention. There are some reporters at Gawker or Salon or so on who might be interested in my story. Every now and then some website does an article on some older male virgin who is at least as interesting as I am. How many of them have maintained blogs for 7 years of futility, huh? Yet I don’t know what a cry for attention would do for me beyond soothe my vanity.

I never expect a new year to get better. I just keep hoping for it not to get worse. I’ve been quite disappointed in that regard for the last half decade.

Happy New Year, faithful readers.

I remain…the Dateless-Man.

So My Mother Has Cancer

“I’ll tell you what I want. I want something now. This is the life I got left. You know what I mean? You get it, Warrior!?” — Mercy to Swan, “THE WARRIORS,” 1979

As this blog has chronicled for over six years, my love life has been less than a bed of roses. As if that were bad enough, I hate it when other affairs interfere with it, such as my three-plus year eviction saga. But it often feels dishonest to gloss over something which is effecting other areas of my life. And so here it is. As if my elderly, disabled, divorced and poor mother hadn’t suffered enough, we learned in November that she has cancer. I won’t get specific but one surgery required her to spend a third of the month in the hospital, and the second (larger) procedure will likely do the same in December — right after she turns 65. And that is assuming it all goes well, and she recovers well, and her quality of life isn’t too shot.

It means racing to the hospital seven days a week, and after work for five. It means fighting with hospital staff to let me see her after visiting hours since there is no way I can commute from work to the hospital in under an hour (unless I was shot out of a canon). It means seeing her look weaker and weaker, and the stress about any random midday call on my cell phone (which is usually still a robocall about my non existent car insurance anyway). It means helping her survive the mess that is American healthcare, which is usually all for making profits at the expense of patient care (or dignity). And it means that what little spare time I did have is once again gone.

It just about killed me going through that for the last 2-3 years of Grandma’s life back in the late 2000’s, and I was still in my 20’s then. I had a ray of hope, some more youthful energy, and mother to shoulder the load. Now I am alone, watching the system pick her apart with renewed energy.

I try not to wallow in too much self pity. I am far from the only single child to face the prospect of losing a parent before I am ready, especially to cancer. I’m far from the only person to deal with that before turning 40. Some people never got to know their mothers because they died so young, or they were given up for adoption or abandoned. And at least for the moment I have a job, which was something I didn’t have for a chunk of my 20’s.

But what is gone is the notion, even when I was 29, of the potential for things to get better and for me to finally have a chance to thrive and make up for lost time. To finally get those joyful adult moments people brag about having or seem to have, such as love, romantic bliss, sexual adventures, and just being without it having to be work or an errand or recovering from one or the other. I am almost 40, which was the age when my mother became disabled and her dreams basically died. There are too many years behind me to make more of what I have. This is “the life I got left.” And there are many times I’d like to leave it somewhere.

Some of this is nothing new. In June 2019 I lamented about the upside to “a life not lived” was that being dateless while evicted meant that there was no way I could become one of those “leeches” who uses women for their money (like many men to). Heck, November 2018 was the first time I was titling entries as “a life not lived.” It seems as if something has always come up which has, at the very least, added some unproductive “real life” drama and stress to the background of my life which, in a small way, contributes to my lack of a love life. Mother became handicapped in the middle of high school, and I had to help with her and Grandma ever since. Grandma took turns for the worse during and after college, and during some of the years when I was working and making decent money (enough to date around had I more time). And then after that came some unemployment, mother getting worse, eviction drama and now almost two years of Covid-19. I am getting the feeling that someone up there, or down below, really does not want to make it easy for me to be happy, or to be in the right state of mind to find love.

It is hard to mentally envision where I have to go when where I am keeps collapsing, and it is all I can do to hang on by my fingernails.

Now, I can’t blame life for it all. There are plenty of people out there who go through far worse health ailments and worse horrors like war or hurricanes or whatnot and still find the time and opportunity to meet people or eke out more fun beyond geek hobbies. A lot of it is me, developing into someone without the core confidence and determination to push on despite a lot of my woes. I let them get to me, I take them too personally. I could argue a large chunk of the angst left over from my teenage and college years (which was chronicled here from about 2014-2016) qualifies. I wish I’d let go of some things back the sooner, maybe tried to loosen up more when my friends tried to take me bar hopping.

Because it sure looks like I will never get the opportunity to enjoy much of my life beyond the day to day unwinding now, and for the near future.

I suppose citing the decades long efforts to tend to my family and hold our “modest” (American slang for poor, as if poverty is a choice) apartments together as a reason for why I am a virgin on dating sites or if quizzed sounds more noble and sympathetic than, “I was just too cowardly, lame, and unlucky.” But the end result is the same. This is the time of life when people have settled down, either had their 1-3 kids or decided to never bother, and just coast along the water hoping no storms hit. No one is looking to have any adventures with yet another mediocre overweight white guy with arrested development whose chief qualities are, “Has sense of humor and is not an axe killer.” Because axe killers at least can get a woman excited in the dark. In New York especially, guys like me are not even a dime a dozen. We’re in the “buy one, get three free” discount bin, next to those LEARN HOW TO PLAY GUITAR DVD’s.

Want some positive news? The cancer diagnosis with my mother provoked her to make some phone calls, and I managed to talk to my long lost half brother for the first time since I was about six. Due to his family’s wishes (my mother served as his surrogate in the 80’s for cash, because we were poor and she wanted to also do a friend a deep favor), he didn’t learn about us until he was already grown. It was weird having to act like an older brother for the first time in my life. And it was also weird hearing someone whose voice is very close to mine, who is only about 4-5 years younger, who got to have a life which wasn’t in poverty or dealing with endless family member ailments. It wasn’t perfect, but he’s married; had a couple of kids, had his adventures. Maybe I would have been like that if I grew up middle class.

Still, November was about being thankful, and I am thankful my mother has survived so far and got to come home for Thanksgiving. I am thankful to be gainfully employed for going on three years now for a place which isn’t a barely legal telephone “charity.” And I am thankful for every hour of sleep I get; there seem to be too few of those lately.

I started this blog to record things I had never told anyone about my lack of a love life, and to work through some issues. I guess one of the key things I have learned is that time can’t be made up, and once it is gone, it is gone. And once it is gone, hopefully the life you have cobbled together has some good bits in it, because that’s usually all you get. And enjoy those before they’re gone, too. And that life isn’t fair, and no one dies when they’re ready to, unless you’re mean and rich. Those types get everything.

I wish I’d been heartier back when my primary woe was not getting laid. Because now, I likely won’t have the time or the energy to try ever again.

At least I will have this blog. And my own kinky imagination.

As always, I remain…the Dateless-Man.

Dateless-Man vs. the Apatow Angst

Being an older male virgin is tough enough. Feeling as if there is a deadline attached to it thanks to a now infamous 2005 film only adds some extra angst to the proceedings.

Longtime readers of this blog will note that the period from October to March used to be known as “the loneliest period of the year.” It would begin in October because Halloween is a holiday which, once you outgrow “trick or treating,” it all about couples having fun in public in crazy costumes, and the odd man out is the odd man out even if you’re dressed as Casey Jones or Ghost Rider or Batman or so on. Thanksgiving can seem bleak when it is tough to be grateful for much, and New Year’s Eve is another holiday that involves a lot of kissing and toasts and reflections of another year gone. February is Valentine’s Day and all the PDA’s it inspired (in a pre-COVID world) and March is my birthday, when I officially grow older.

This year I can’t quite say that I am depressed. Morose better describes it, as I am often sullen and ill tempered, at least during work days. Part of it could be a return to the office after a year and a half of working from home; I like getting out of the house, but it involves waking up earlier, having to dress up, and still being mostly isolated as only one other worker is currently in my division. The slow moving eviction drama involving my mother and I since mid-2018 still grinds on, but it hasn’t taken any turns for the worst. Quite the contrary; my mother has a lawyer now, and she actually has a pulse (unlike mine, who mostly marks “present”); a rarity in a lawyer supplied by a non-profit agency.

You see, I am actually 39 years old; and this is the first time I have admitted my exact age here. That means come March, I will be 40. And thanks to Judd Apatow’s “The 40 Year Old Virgin,” that makes my designation as an older male virgin shift into another phase, where I unintentionally and unwillingly become associated with a minor moment in pop culture. And I become another step closer to being a living internet meme

I reviewed “The 40 Year Old Virgin” back in July 2016 (during the blog’s second anniversary). I won’t rehash my sentiments about it here, only to state that while I found it amusing, I didn’t consider it akin to a documentary like some dudes think it is, or even some primer or inspiration like others do. More than anything, this film is responsible for taking the concept of older male virgins mainstream, outside the realm of slasher villains (barely). Virtually any time a website or even dudes on Reddit or 4chan talk about older male virginity (especially their own), they will use some variation of the phrase, “Real Life 40 Year Old Virgin,” as if they were something that was once ordered from a comic book advertisement (like sea monkeys and chicken lips). I’ve seen seen this headline for articles about virgins who were still in their 30’s (or into their mid-40’s). Whether it was a fellow blogger relating their experience or a relationship coach issuing advice, I have seen and read that phrase more often than I care to count. And I hate seeing myself become among them in roughly five more months.

Regret about my status as an older virgin is nothing new. Regret and I are old friends; we hang out together consistently and exchange cards on holidays. You’d think that an outside factor like Covid-19, a once-in-a-century pandemic which has complicated (to say the least) the world of casual dating for nearly two years would make me feel better. After all, for the first time in my life, I could genuinely blame an outside factor in my lack of a dating life and it isn’t some shallow excuse. Perhaps I am being unfair to myself for dismissing previous “excuses” as having to spend a great deal of my spare time as a young man (and now an older adult) helping to tend to my ailing grandmother (who died in 2010) and now my ailing mother (who became handicapped towards the end of high school), but the truth is there are plenty of people who have had to deal with far worse in terms of family drama and social strife, and they still managed to have a love life. But all this Covid-19 era does is remind me of the years, even as recently as 2019, that I arguably squandered. And I realize there are literally dozens of people I have crossed paths with online over the past 15 or so years who would and could say, “I told you so,” but I was too stubborn to listen. I insisted that I resolve the problems in myself before I make them problems for others, but perhaps I allowed good enough to become the enemy of the perfect for too long.

That and I just genuinely do not believe any reasonable woman I liked could possibly like me back. Which does a lot to stifle my desire to go through the slog of trying to land a date via online sources (since my real life/warm approach opportunities have long since evaporated).

Fortunately, I do live in New York and the general vaccination rate here is higher than in many other states. I have been fully vaccinated since the end of April and I wear a mask whenever I go outside. I have even attended exactly two movies this year in a (mostly empty) local movie theater. And I realize that the risk of contracting Covid-19 while on a date will never be zero percent, much like the risk of being run over by a car or shot by a mugger or crushed by a falling piano will never be zero percent. But the fact of the matter is that until Covid-19 is in “memory territory” and not “still killing almost a dozen people a day” in NY, any attempt to date is not only increasing the risk of death or permanent disability onto myself, but my elderly, handicapped mother. Does she deserve to be at increased risk because I chose 2021 of all years to try harder to get laid? No she doesn’t. But that is still time lost, still months off the clock, and it is still my fault for letting it get this way. I wasn’t strong or smart or willful enough to not let all of my traumas, real and imagined, from childhood thru college ware me down to the point of inactivity.

I suppose the one boon to this is that becoming an “official real life 40 year old virgin” is potential novelty. Should I decide to acknowledge my virginity in a potential dating site profile, it is an easy reference to make. The problem, as I laid out previously, is that it is a subject that I am not comfortable discussing in real life with friends and family; much less admitting it to strangers. I might increase the odds of attracting someone associated with a fetish or sexual curiosity, but I am unsure if I want my dating approach to consist of being, essentially, a “Bedroom Pokemon” (“I am a wild Viginasaur, Flattery is Super-Effective!”). It would cut out a lot of future stress (i.e. having to bury or downplay or compensate for my staggering lack of experience with dating, kissing, hand holding, etc.), but having a woman I am about to see for a coffee know my most shameful secret before anything else is anxiety inducing unto itself.

The biggest irony? I have saved up enough cash that were Covid-19 no longer a problem, and the risk of eviction was not present, I could easily take that trip to Las Vegas and finally become a real man. My job actually offers paid vacation time, and some hotel suites are pretty cheap (under $90 a night) if you go during off peak hours (basically, Tuesday thru Thursday). And as much as my opinion on that has “evolved” over the years, the pressure of not wanting to be an “official 40 year old virgin” could have been the final justification for taking that trip. Yes, there is the risk of an STD, but in Vegas prostitution is legal and part of that involves sex workers staying healthy and having health insurance. Arguably the risk of an STD under that circumstance may be lower than if I hooked up with a random woman at a local bar (even if the latter is more socially acceptable). There is some degree of shame to having to lose my virginity by paying for it as if I were a circus freak, but to be honest, most people’s first sexual experience has come degree of awkwardness, imperfection, or shame to it. And covering it up isn’t terribly hard nor the worst of lies to make. “My only time was with a prostitute named Chastity in Vegas” is only so many shades removed from “my first time was with a woman named Chloe I met at a bar/club/friend’s wedding/clown college” anyway, so long as I got tested and kept clean. But have you seen the Covid rates for Las Vegas!? Talk about increasing infection risk! So not even that “failsafe” is safe anymore.

The smart thing to do would be to hunker down, wait a tad longer until Covid-19 gets even more under control, and then try to make up for lost time. At least I wouldn’t be the only person having a dry spell (even if mine is drier than the Sahara). But by then it may be 2022 or 2023, and the older I get, the slimmer my chances to ever have sex (or heaven forbid, a happy, fun, and healthy romantic relationship or two) without paying for it becomes. The fact that this latest hurdle totally isn’t my fault doesn’t completely eliminate the fact that the previous dozen hurdles were at least partly my fault. I was the one who was too proud to beg my friends for help more. I was the one who was too stiff to live it up more when they tried to take me to bars or a club. I was the one who always tried to act “too cool for school” to cover up how shy, awkward, and scared I was. I was the one who wasted all three chances I potentially had as a youth, in part because of my own fears and anxieties. I assumed I would get more and I was horribly wrong.

If I could see unicorns or have super strength like Sir Galahad for being a virgin, it wouldn’t be so bad. But instead my own super ability is regret and longing, which is less useful than talking to fish. Yes, even us “almost 40 year old virgins” get to mock Aquaman. But even he has a queen. What do I have, besides my “mattress of solitude?” And if I wasn’t good enough to attract women in an era before random encounters could result in mutual death, what chance do I have now? I simply don’t know how to proceed, or even if I can proceed. And I am not looking forward to being nothing more than being the real life (and less fit) version of a Judd Apatow character profile.

Happy Halloween, everyone! And remember, the worst monster is always humanity, so those who aren’t wearing costumes are the scariest of all!

Dateless-Man Gets As Close As It Gets via Online Text!?

I honestly don’t know how I get into these situations online. I’m not on Twitter, or Tumblr, or Instagram, or TikTok, or Twitch, or YouTube, or the Matrix, or Kryptonian Crystals. Only two of those are fictional. Heck, I don’t even surf on Reddit or Kiwifarms or 4chan or the other dregs of the Internet. I have the internet presence of an 87 year old grandmother. And yet for the third time in less than three years, I have stumbled across a younger woman online who wanted to play out kinky scenes via text role-playing. The biggest difference is this time I wasn’t at a message board which caters to a fetish, like I was the previous times.

This time I was on a Facebook group for fans of a particular anime franchise. No, I won’t reveal which one. I joined it last year in part to share some (non kink) fan fiction I made, and because I was a genuine fan of that franchise. On the surface it seemed like a sane group, relative to Facebook. It even seems to be moderated by mostly women, which is usually a plus so things get less toxic. Once I was there long enough, however, I realized that a secondary purpose of the group was to showcase how much most of the female fans like one character in particular, in a romantic way. It’s all harmless; just sharing a lot of fanart of them. There is definitely a bit of equal time with the franchise’s lady lead, but because the group does consist of at least half women, I’d say it does cater more towards the beefcake than the cheesecake amid discussions about various episodes, movies, and soundtracks for the franchise.

Perhaps I did ask for it by replying to a topic. A woman in her mid 20’s asked everyone if they had ever done role-playing before. And as someone who has done tabletop role-playing (with dice and character sheets) in high school, part of college, and even briefly from about 2011-2013 with some friends doing a Dungeons & Dragons revival, as well as managed a message board game for over a decade, I replied affirmatively. This woman — who I will dub “Kay” — private messaged me within a couple of hours and was immediately lobbing her “original characters” (known as “OC’s” in gamer talk, not to be confused with the 2003 TV show, The O.C.) and asking me which characters I wanted to play.

Things started innocently enough; Kay was role playing her own character while I was managing most of the anime franchise characters. It was very similar to what I’ve done before with the message board game I run (which is based off of a comic book franchise, not anime, but the lines between are blurry). But once the characters met up and went past some of the standard tropes of the franchise, things got “mature” very quickly. Not only does her character more or less transform into a more aggressive form and wants sex, she wants a threesome. And this isn’t the PG-13 grade stuff at my message board where players and I respectfully “fade to black” when things get beyond second base in type. Kay wanted blow by blow, thrust by thrust input.

Imagine the absurdity of a nearly 40 year old virgin who has been on three dates in his entire life and who has never so much as kissed a woman being tasked with doing a text roleplay of a hot and steamy threesome with another woman over the Internet. That is the situation I found myself in sooner than I realized. And to be honest, had Kay been up front with her intentions and indicated that her roleplays would shift into X-rated material pretty quick, I may have passed. And to be fair to Kay, I did note some awkwardness about this and she gave me the opportunity to gracefully bow out. Incredibly, unlike the first young woman I got involved in something like this with — who lied about her age — Kay made no attempt to blur the line between fiction and real life. She has a boyfriend in real life and made no attempt to “hit on me” or ask a ton of personal questions like the first young lady (of Kink Panther fame) did. In fact, Kay is all business. Just there to get in her super freaky RP’s starring anime characters sleeping with her character, toss in some chase or action sequences, and go on with her day.

Ultimately I agreed to continue once it became clear the text roleplay (again, think CHOOSE YOUR OWN ADVENTURE, only in a private message window and not a book) would get steamier than I was used to writing. I can’t quite say why. Was part of it ego, as in not wanting to risking coming off as shy and nebbish to a total online stranger? Yes, probably. But another part was a test of my imagination. Here was a perfect opportunity to “practice” such a scene intellectually with another person in as clean and sterile a way as possible where the context made sense and nothing was on the line. Especially with a stranger, not someone I know, under the cover of the expectations of the characters and the franchise.

It was awkward; I will not lie. But it gave me an excuse to sort of intellectually go through the steps of what I think “good love making” should be like (while staying in character, of course). Start out with kissing and heavy petting, then onto some oral sex (on the woman, unlike Batman), and then after comes my, ahem, organ. Of course, real sex I imagine varies from partner to partner, as everyone has their own taste and method. That is the other good element about text roleplay; I have to be reactive. I can only work with what she gives me, and vice versa. And considering she is still wanting to roleplay and made no comments like, “seriously, you think THAT is a good idea,” I must be doing okay. If anything, I am amazed at how voracious Kay is. She seems to live for those scenes and want them to go on forever with characters she likes. And she’s advertising for more role-players again! I’m not enough for her; she wants a whole harem of keyboard jockies! Is there a male version of “harem?” If not, kind of shows how sexist language is, doesn’t it?

So, to recap, “how I spent my summer vacation” has involved writing kinky fiction under an alias on Deviantart and, apparently, stumbling on even more hardcore stuff just being a geek online. I wish I was just smooth and lucky in real life all those years in college. Online I’m a sexy beast, while in real life I’ve had the least! But maybe that is par for the course online; few of us are ever completely ourselves on it. At least with something like this, the lines are clearly drawn. And eventually Kay will get bored and move on, as much RPers do.

At least I hope so. I don’t know if I have another threesome narrative scene in me to write.

Who would have thought I’d manage to express myself as sexual being online, at least modestly thru text, during the pandemic? Maybe experience isn’t all its cracked up to be, or at least can be compensated for to a degree by imagination and tenacity? Most guys my age are “three pumps and a beer;” that could work in my favor with many an unsatisfied woman over 35. Maybe I might even be able to do “good enough” at sex that there is no suspicion about my secret, and I don’t feel obligated to reveal it as an excuse for a lackluster performance.

“That was the worst sex I ever had in my life!” “I have a good reason! It was my first time!” was not the scene I was lookin forward to. Playing a character in text is far from being myself in real life, but there’s only so many ways a guy can “rehearse” without an inflatable doll.

Maybe part of it is reaching an age where I give fewer ****’s about things. I mean, I am a virgin; by definition, I have given zero ****’s. The flesh has been willing, but the confidence has been lame and the charisma has been lacking. I’m as close to 40 as I can get and I am still in this situation, with a pandemic stealing time from me. I may as well experiment with kinkiness via my keyboard when I can. It’s not like I have any other viable options at the moment.

As always, I remain the Dateless-Man. Thanks for reading.

Dateless-Man vs. An Awkward End to a BBQ

Despite the rise of the Delta Variant of Covid-19, things in New York are slowly moving closer to normal in terms of outdoor activities. I am vaccinated but still wear my mask outside, due to not trusting other people and having a chronically ill and immune compromised mother at home. But one step closer to normal happened last week when I was able to attend one of my friend’s annual birthday barbeques that he has outside his apartment building. Naturally, last year was a no-go, and he was ironically was one of the last of my friends that I hung out with pre-Covid on January 1st, 2020. I have occasionally written about this pal before. Since it has been a long time, I may as well restate my blog policy on names. I do not reveal the real names of anyone in my life, regardless of gender, for the sake of privacy (mine and theirs). I usually take the letter of their first name and make up a fake name with it.

Except for this dude, who I dubbed “M****” due to being very lazy back in 2014 when this blog was in its infancy (and when I probably should have channeled that energy into OkCupid instead). He is one of my oldest friends, whom I met in junior high during what had been a usual awkward era of gym class. In between being bullied hard in 7th grade, I had to deal with being picked last in any sporting event since I stunk. M*** had some basketball skills, but he was too much of a slacker to care and we would just chill and tell jokes the whole period. We later attended the same high school and become better friends afterward. He was the only one of my male friends who was also raised by a single mother and came from an impoverished home, and also the only one besides me who is not married. He isn’t a virgin, although I am unsure that he has had too many sexual experiences, at least in comparison to some of my other close pals. At any rate, he hasn’t been featured in one of my blog adventures since 2018, so he was due for a return!

M****’s barbeques (or BBQ’s) are casual, low stress affairs. Burgers, hot dogs, sausages (which I do not eat), and some beer which is usually kept cool in a kiddie-pool full of ice. Since I had work that day, I wasn’t the first person to show; but then again, they never start exactly when they are scheduled to for various reasons. And these events rarely have too many women there; the ones that are there are usually there with their fiances or long term boyfriends, or are M****’s older relatives (like his aunt or mother). This event was no exception; I showed up at 6:30 p.m. when the sun was still out and within a few minutes I had a burger in me, was nursing one of three beers, and engaged in some low key, fun conversation with close and casual friends.

More guests emerged in time, and now it will be useful to whip up some fake names. All of them were people I’ve known for years, but have never been especially close to — associates, essentially. One I shall dub Fred, who works at a cemetery and is known for vast knowledge of animals and having a screw or two loose. Another I shall dub Harry, who is a postal service worker who is divorced with a son, and who has basically begun to resolve a midlife crisis by working out. And finally, there is Norman, who is one of M****s dozen or so cousins who has long hair, is an ex-drug addict who has a common law wife, a kid, and is also a few pencils short of a set. I’m not exactly normal myself, so I tend to attract those sorts of people around my orbit. And in recent years, I’ve kind of preferred it, because I have learned that “normal” people tend to be very boring, judgmental, and unimaginative.

As you might expect for a social gathering involving mostly men, alcohol, and meat, a common subject as the night wore on is women. Both Fred and Harry are avidly dating around, and when Harry first arrived (later than everyone else, which is typical of him), Fred spent about an hour trying to hound Harry to convince some of the women that he knows from his social media feeds to show up because “this thing is a sausage fest.” In a sign that men can be just as full of drama as women are (if not more so), it eventually came out that Fred and Harry both dated the same woman — who had a reputation as being toxic who tends to leave men worse off than they were before. There had been some kind of tension between the two over this, but by the end of the night it was over and they were on good terms.

I knew these guys “dated around,” but as the evening continued and various conversations were had, I soon learned the vastness of it. Both Fred and Harry claim to have slept with over 100 women, and virtually everyone at the BBQ, including some of the women there (who they did not date) seemed to confirm this. I know men typically exaggerate their sexual “conquests,” while women undercount theirs (due to the “double standard” baloney), but not a single person present seemed to question their claims. They all hung out together more often without me present and often saw them with different women on their arms over the years (to say nothing of social media pictures). And the reaction to this by M**** and the rest of the dudes at the BBQ to this reputation is one of public snark and private approval. By this I mean that both Fred and Harry’s promiscuousness were teased about during the evening, with terms like “man-slut” and “man-whore” being bandied about. However, when these mocking terms are used, they are not said with any hint of malice or disapproval, but with a kind of a smirk and a wink behind it. A part of this is social expectations, which include the fact that there is no male term for words like “slut” or “whore” so in order to compensate, the word “man” has to be crudely attached to the front. Norman also seemed to have a similar reputation, although not quite as high, nor as current.

Thankfully, I have come a long way since the start of the blog, and I did not feel depressed or envious over this. Nor did I gather this information by asking deeply personal questions like a creepy TMZ reporter. Instead I utilized my well honed technique which I call “being the fly on the wall.” In that I pay attention to the conversations around me and remember details. I have actually gotten better at this ever since I started working as a telemarketer/caller center representative since such attention to detail is key. I am the type of person who could be told by a date what her favorite color, band, and drink are, even if indirectly and I would remember it over time. It’s the sort of thing which might impress a woman, if any were to actually be romantically interested in me. I did pay attention to Fred, Harry, and Norman to try to observe what about them made them appealing to women, or at least to gather info in general.

I suppose all three are conventionally attractive, and all have tattoos and various piercings. All are relatively in shape (more than I am), although over the years Fred has developed a slight belly in comparison to a decade ago. They all are confident go-getters who are passionate about whatever topic they are talking about, even if it is one that is full of crap. They each also admitted, and were teased about, the fact that their high numbers are due in part to capitalizing on any opportunity, regardless of how they felt about the woman privately. Whether the woman was wasted or below their standards in looks or personality, none of them could resist an invitation. These are three fellows, who if they saw the opportunity for sex with my mother’s gross older friend as I did, would probably have taken her up on it, if only for the story they’d have to tell about it afterward. While they all strive for quality, they will scoop up quantity if that is all they can get for a stretch. These are men who considered going without sex for a month as “a dry spell.” I’ve gone without sex for about 25 years; my “dry spell” is old enough to drink and rent a car. On the surface Fred and Harry are all smiles and excitement over their bachelor lifestyles, but as they’re in their late 30’s like I am, there was a part of me that was genuinely curious if it was masking a longing for deeper intimacy. At least all of them went through some version of a nasty breakup (if not several) without deciding to hate women like “the MAGA Man” in 2019 did.

Fred, at least, has some demerits to his lifestyle which came up over the course of his appearance there. For one thing, he is not above cheating on lovers; a fact that M****’s best female friend (and possibly his ex, I am uncertain) made abundantly clear. For another, Norman griped about one time he was trying to set up a date between M**** (his cousin) and a local neighbor, and Fred knew this and tried to scoop her up anyway (which in guy circles is called “cock-blocking” and is as unforgiveable a sin as acknowledging weakness or cuddling). Although Harry certainly has the allure of being smarmy, it seems that Fred is more mercenary and is willing to bulldoze over others to get sex. That is hardly rare in dudes, but it was clear that even though Fred was among friends, they hadn’t forgotten this.

All of this was just casual social science research between beers and burgers (and one-liners) for me. As the title suggests, things only got awkward towards the end of the evening. The crowd had thinned out a bit as the sun went down and the hours got closer to midnight. In a scene eerily like the opening of the 2005 film, “The 40 Year Old Virgin,” all of us happened to be sitting in a circle and to a man, everyone was talking about various sexual experiences and the body parts of women, and the types of sexual acts they enjoyed (such as “giving head” or performing oral sex on a woman). This included some discussion about initial sexual experiences, when I was shocked to hear Norman claim he had first had sex at age 13 (with a girl who was 15). Even for most “bro circles,” they might consider losing virginity around 8th grade to be a tad young.

The more they all spoke, the more tension I felt, much like Andy did at the start of “40 Year Old Virgin.” For those who have not seen the film, Andy’s secret is revealed when he attends an “all guys” poker party with his coworkers and his inability to accurately describe what breasts felt like once the discussion topic shifts to sex and women leads to his virginity being revealed (and a lot of public humiliation and mockery). M**** knows I am a virgin, or at least he did years ago; we don’t talk about it much, as I never bring it up. It is part of the quiet unspoken deal between me and most of my (male) friends where they never ask me about my love life, and I never reveal anything about it. As the only guy in the circle who was not talking about previous girlfriends or sexual encounters, I was concerned that it might lead to some sort of awkward question thrown at me.

I have sometimes expressed anxiety about situations like this in previous posts, and especially in entries I used to make when I previously posted on Doctor Nerdlove‘s forum. Often the advice I was given included the utter denial that adults outside of college randomly talk about previous lovers and sex in casual conversation, followed by the pointer to keep it cool and claim “to not want to kiss and tell” or to “be a gentleman.” The only problem is absolutely no straight men in New York who have ever had sex would fail to mention it were it to come up in casual conversation to the point where they were asked directly. Not a single one. You could ask a rabbi about the last time he got laid at a party and he’d give some sort of bragging answer. So a response like that would automatically be suspect.

The lesson I learned from Andy, even if it was just a movie, was not to panic. To not be in a rush to contribute to the conversation and only consider what to say when forced to. After all, if my secret shame is destined to be revealed at a public BBQ, then why should I be in a rush about it? I also know the philosophy behind lines such as “he doth protest too much,” and that trying to overcompensate can backfire. Above all, to only answer such questions in vague trivialities and short answers. The longer I could contain my awkwardness, the better the chances that the winds of the conversation would change, such as to the topic of films or YouTube memes. And sure enough, that was exactly what happened. With enough time, the near metaphysical measuring contest ended before I even had to reach for my belt.

I suppose the lesson out of all of this is that the people in my life who would make the biggest deal about my virginity are fellow men. They are the ones who likely to enforce stereotypes about it and lead a chorus of potential mockery about it. As embarrassing as it would be to reveal my virginity to a woman, and as possible as it is that she may mock me or see me as lessor over it, men are more willing to go out of their way to comment about it. Of course, there was the chance that the exact opposite thing could have happened; the dudes could have been all so torn up about it that they sought to go “on a mission” to “find me a woman” as a matter of male pride. But I do not want to find out, and even the latter would be annoying.

It was this last segment which made the episode something to type about. That despite facing an eviction and a pandemic, that there was still a chance of life imitating art in a bad way. It will be another month before my next court hearing and I am still hesitant about dating for a variety of reasons, least of all contracting it and bringing it home even if my vaccination makes may make me asymptomatic. I am losing the battle of time, even if it is very unlikely that I could get a date in a month regardless of the circumstances, unless I appeared on TV after winning the lottery. And even that wouldn’t be an ideal way to do it.

At least I ducked it this time, and didn’t have to explain myself amid flat beer and cooled hotdogs. That would have surely been a drag on a worknight! Maintaining my alter ego as the Dateless-Man can be stressful at times, but someone has to do it. And thankfully, I have decades of experience. I’m not some rookie like Andy was.

Take care of yourselves, everyone who has read this far. At least for another month, I remain…the Dateless-Man.

Dateless-Man vs. Platypus Post II

Last January, I began what was to be an eventful year (in terms of the pandemic, not my love life) with what I dubbed “the Platypus post.” Why? Because much like the Australian mammal, it had a little bit of everything with no main theme. And there is where I find myself now. I already missed May due to really nothing major to report, and I do not want to miss two months in a row (like I did last year). I suppose if this post fits any “theme,” it will continue the trend of 2021 being the year that I delved into expressing myself more through fiction, either as an attempt at therapy, boredom, or a sign I am losing my damn mind. Or some combination thereof.

Much as before, these will be broken up with bold text. Call it a Dateless-Man mission report straight from my noble post at the “Mattress of Solitude” (TM)!

Dateless-Man vs. Covid-19 Update

As of mid-May, I am fully vaccinated via the Moderna shot. I took both shots in April, but since the last one was near the end of the month and it takes a fortnight (the pretentious word for 2 weeks, not a misspelling of a video game) for the vaccine to fully take effect within the body, that means I was all anti-bodied up by about mid-May. I had been warned that there could be some aches and lethargy from the second shot, which I acknowledged by scheduling it for a Friday so I’d have a full weekend to recover before work. And boy did I need it, because I felt weak as a kitten for about 36 hours. I still did all my chores, but I also spend most of that time in bed or staggering around. But, it was worth it to finally turn a corner on this pandemic. Vaccination rates are at 70% in New York, so most restrictions are limited aside for transit, hospitals, and super large indoor gatherings. And we’re still going by the honor system in terms of people being vaccinated, and that seems a bit misguided. Most people have no honor.

I do have my concerns about the Delta variant, which is spreading across the nation since we still have so many unvaccinated people in the U.S. and therefore so many petri dishes for the virus to mutate. But at least I have made myself as safe as can be, as has my mother.

Seriously, get vaccinated, everyone.

Dateless-Man vs. Hairlines, Part 2

One downside to waiting until I was fully vaccinated was that I waited too long to go back to my barber, and now he’s closed down. He’d been my barber for about a decade and he was an old school dude who knew how to cut my hair. I usually expressed difficulty getting others to cut it the way I liked for years until him. I’m not like one of those guys who is fine just spinning in a circle with a barber holding an electric razor for 5 minutes; my hair is curly and the front especially has to be cut with some consideration, or I wind up looking like Lloyd Christmas from “Dumb & Dumber.”

So now I’ve basically decided to let my hair grow long. I had a mullet for the first few years of college (which may help explain why I was single), but now it’s just all of my hair being long. It may not seem like a big deal, but I hate breaking in a new barber and if they goof up, it’s months before new growth negates it. The sitcom “Married…with Children” once had an episode about Al Bundy losing his regular barber and the woe it wrought, which I can totally relate to now. I just don’t that kind of time, even if I want to entertain the possibility of dating again.

First I feared a thinning hairline. Now I just let it grow unfettered! But at least I don’t look too bad with a short, bushy, “Fox’s Peter Pan & the Pirates” style ponytail.

Dateless-Man vs. Eviction, Continued

Due to a new executive order from the governor, our endless hearings have been postponed until September. That will be a break of two months, the longest we have had from this madness since 2019. To think it has been plaguing my life in some form or another since April 2018. It genuinely gets hard to focus on much else besides work with that impending economic doom hanging over my head constantly. But, hey, a 62 day reprieve! I’ll take it.

Dateless-Man vs. More Fetish Fiction Writing

At this stage my Deviantart side-hobby has been rolling for almost 3 months now. I am still averaging 2,000 views and about 10 “faves” per story, and I am averaging 3-4 stories a month. Some of them have done way higher (i.e. 7000 views and as many as 23 “faves”). That is still small time compared to the top dogs of the format, but I still consider it impressive considering I am a man out of nowhere (even if I have some minor recognition within the “community” (i.e. forum) I had posted at earlier in regards to this. Honestly, a good chunk of the reason why I did not post here in May was because the spare time I had available for it was spent writing a fetish tale, and there was little to report anyway.

For perspective, this blog never had that kind of viewership (nor do I want it to, to be honest), and even the more straightforward geek articles I used to write semi-professionally online for a website rarely used to average quite that much per article. And while the readers are commenters there are 99% men, it does feel good to have some level of acceptable regarding my fetish, which I am more shy about and consider a bigger taboo than even my older male virginity (which is a feat considering how close I am to forty these days). People compliment my imagination, and while it is mostly being used for kinky stuff, I do genuinely try to make the stories readable and workable beyond that. Some writers just do “the scene” and that’s it; I try to have a clear beginning, middle, end, a plot, and even sometimes character development. Dialogue is fun to write sometimes.

I am not at the level of acceptance about it where I will reveal it here, or mention it to a date, or even hint at it to someone I was in a long term relationship with. But expressing it makes it feel less buried, and I do think the outlet has been a net positive. It feels less like yet another part of myself I feel I must lock in a box and never reveal. Even though I know that only expressing it via fiction online under yet another alias may seem pretty close. Call it placed in a closed but unlocked box. If a woman I was in a long term relationship with admitted to it being her thing of her own volition without any prompting from me, under that circumstance I would acknowledge it, because it would be to aid in her pleasure. And as small as this sounds, it’s progress from a few months ago.

What Would I Put In A Dating Profile, Anyway?

This leads me full circle to what I pondered on Leap Day 2020 (which turned out to be less than 3 weeks before major Covid-19 lockdowns began). As I stated at the end of the year, while many “lost dating years” could be fully attributable to my own trauma, drama, stressful circumstances or lack of confidence (i.e. general cowardice), 2020 could not be. Covid-19 hit everyone. The lockdowns, social distancing, and danger was real. In fact, it still is real. I know I am hesitant to go to a packed movie theater again or a bar or restaurant, at least without a mask on most times, and I know I am not alone. It isn’t so much that I fear death myself, but that my mother is very high risk if I bring it home to her. Were I to catch it running normal errands, at least it could not be helped. If I bring it home because I wanted to get laid, well, then that is on me.

Considering it took time to get vaccinated and for things to slowly reopen again, it could be argued that it would have been folly to try to date again before, well, now. Ideally, I would have some cold approach possibilities via friends or associates, but those wells dried up ages ago. And various MeetUps are virtual now, which defeats the purpose. I don’t want to do virtual; that seems beyond artificial to me (and an easy way to get “catfished”). This leaves online dating, as haphazard, random, and ineffective as it usually is, as my least worst option. That means OkCupid or Plenty of Fish.

My only other option would be to travel to Las Vegas and lose it to a sex professional where it is legal, and therefore she is likely to be healthy and not as exploited. And the irony is I have actually saved up enough cash that, were I not worried about being evicted and having to move to a new apartment at any given moment, I could afford to do it now. Some hotels offer $80 a night if you go during off peak days (i.e. any day that is not Friday or Saturday). It’s a long flight from NY, but shouldn’t be as long as to California (where I have gone twice in my life). And I even have a job which has paid days off (which I have to spend being available for housing court). But it does seem reckless to blow a few grand on that when I may need it all for a security deposit somewhere before Christmas.

And it means solving that dilemma of constructing a Bio which is truthful and genuine without lying or, as I did in college, going too far in the other direction and just splattering my faults and baggage all over. Especially since my two genuinely good traits — my sense of humor and my writing ability — are skills that need to be shown, not told, to make an impact. Simply typing, “I have a sense of humor” on a Bio is worthless; no one claims to be “humorless” online. I have to display it by writing a truly funny Bio, without being dishonest or crass. And I have to do it in under 100 words per Bio section, as studies show that anything longer tends to dull interest.

To say nothing of uploading recent pictures, with my long hair and the fact that I have likely gained some pandemic weight. Maybe I should brag that I have twice the dadbod now. I’m in shape; it’s just not aerodynamic. And to do it all in 2 months before the next court drama or before I get any older. If the pandemic has taught me anything, it is that life is short and we only get one chance at it, and I have blown many of them. I will never have certain things, and that includes certain types of romance. I will never have a successful carefree high school or college romance, where things are innocent and it is okay to be broke. I will have less time to develop a learning curve because I am already old enough and I literally cannot waste any opportunity. The romances I get in my life will likely be a pick of people who are, well, left over. Without the ignorance or innocence of youth, all of us will be jaded and micro-analyzing any flaw or misstatement. Of course, I shouldn’t talk — I’m am overweight virgin with a weird fetish and a gross lipoma on my back fretting over a receding hairline with average looks and height — but there is a part of me which is angry at myself for being so emotionally incapacitated that I did not try harder even five years ago. I am not in my prime, and neither will the dating pool which remains for me. It might have been nice to have dated when I was, like everyone I know seemed to do. Now I am an also-ran fishing for fellow also-rans. Genuine love and connections are possible, but it is more likely a mutual fear of dying alone may be an underlying factor. I am at the age where no one with any sense chases after what they want; they settle for what they can get. And that feels less magical, I suppose.

I read some decent advice from someone who snagged a fairly inexperienced lover of her own who claimed the best thing to do was to try to be that “diamond in the rough” that can be a reward for someone who has the patience or luck to find you. The only flaw in that is that my confidence is still hardly ideal and I would genuinely distrust someone who treated me like I was their special prize. I would expect an angle, like Gordan Ramsey and Jon Taffer emerging somewhere with cameras and telling me I was suddenly on “Virgin Rescues” on TBS. If a woman looked at me lovingly and said, “What did I do to snag a guy like you?” my only answer would be to shrug and reply, “I don’t know; you insulted a magician?” If someone asks me why I didn’t date much before the pandemic, I have to list excuses to avoid the answer of, “too lame and chicken-spit”. “Why did no other woman snatch me up first? Baby, you were the only one dumb enough to try,” is honest but does not work in any context. And yes, as someone who understands fiction and words, I know it is not encouraging that my first inkling towards hypothetical women who like me is to offer only distrust and insults. Burying those Id urges, honestly, may be more essential and more of a challenge than burying that I am a virgin or have a fetish. I simply don’t have much more time to reach a state of spiritual and emotional understanding before trying to date again. This is as good as I am going to get. And at least I am better that that dude begging for cigarettes on the street corner.

Still, this is a unique point in history. All of us have collectively survived a once in a lifetime event. Maybe that will lead to more understanding and open mindedness. And maybe despite my flaws, I find a truly special woman who I am able to complete despite my own jadedness. Such happy endings in life, in my experience, are fairly rare. But if I don’t try, then I have already failed. And as bad as I regret my failings in dating, I think I regret the opportunities I missed even more.

And that’s that for June! I hope everyone who reads this is safe and happy, and has a great summer ahead of them. Maybe next time I will have more hopeful or dramatic news for the blog.

Until then, I remain…the Dateless-Man.

Dateless-Man vs. Covid-19, Hairlines, and Fetish Writing!?

That’s right, we’re covering all three topics for this installment! With my endless eviction drama nearing its third year of involvement (near domination, really) of my waking life, I wanted to focus on some stuff which is happening aside of it for now which does connect to the premise of this blog. And seeing that I have gotten a host of new views and hits (especially on April 18th, for some reason), I may as well summarize it. As an older male virgin in his very late 30’s who has only been on three romantic dates, three speed dating events, zero kisses and one accidental breast-touch (which is my most highly viewed post), I set up this blog to review my own futile romantic life and times. It began as a simple catalogue of all of my major experiences with the opposite sex going back to my first unrequited crush in grade school and finishing with my “last date” in college. And beyond some speed dating events (the last one in 2015) and a few lamentations for an associate or some coworkers here and there, that’s mainly been it. The cataloging was mostly wrapped by 2016 and since then it’s been various essays, ponderings, and lamentations of various lengths and degrees.

That’s not as succinct as “previously, on X-Men,” but it will suffice. So let’s tackle each subject one at a time, shall we?

Dateless-Man vs. Covid-19

Much like the rest of America and the whole damn world, I have been effected by the global pandemic. I’ve had to work from home since late April 2020 and adjust much of my lifestyle (or lack thereof) after work. It also has made casual dating more theoretical than practical in a manner beyond my own insecurities, fears, and doubts. I wonder just how many people who aren’t married or cohabitating have gotten laid within the past 10-11 months, especially in “hot zones” like NY (where I live), CA, WA, or even Michigan. With a very real risk of either contracting a deadly disease and passing along to a relative, friend, or coworker even from non-romantic activities, I imagine only the reckless, desperate, and/or extremely horny have bothered to even try to date during these times. With lockdowns making most outside activities null and void, it also diminished interest and practicality.

Unfortunately, there is nothing like a pandemic to make one truly consider concepts such as wasted youth or missed opportunities. For most of us, dating and or the very attempt at a love life was essentially put on hold for a year, and it was absolutely none of our faults. There are far worse things to worry about, like joblessness, homelessness, death, and disability, but somewhere on a top 20 or 50 list, a love life will pop up as a concern for most.

However, slowly but surely it seems as if things are trying to return to normal. Indoor dining in coming back in limited capacities, and outdoor activities are okay so long as one’s been vaccinated. And, hey, vaccines! They’ve become more readily available since even this same time three months ago. NY has an utterly complicated and frustrating website system for making an appointment, and once slots were available they usually were gobbled up faster than press passes to the New York Comic Con. Thankfully, as an insomniac, I happened to be up when they freed up on the even of Good Friday, so I grabbed one up.

Come to think of it, why is the Friday before Easter called “Good Friday?” It was supposedly the day Jesus Christ was crucified. It certainly was not a good day for him, even if you accept him as a supernatural martyr and savior who willingly “sacrificed himself” to rise again. Bring crucified is a horrific way to die. It wouldn’t matter to me if I could regenerate like Deadpool or the Crow, I wouldn’t consider a day I was crucified as a “good day.” I think the concept was that it was a “Good Friday” in the sense that the resurrection of Easter kicked off faith in Christ as “the savior” around the world forever after. I still find that kind of callous, and I wonder if more people of faith would focus more on what Christ said and did when alive, instead of focusing so much on his death to the point of endless visual recreations, some of them would act more like he intended (and not, say, be televangelists). But this is a tangent by an ex-Catholic school kid turned atheist.

So at any rate, I got my first Moderna shot on April 2nd, and am scheduled to get my second on the 30th in the wee hours of the morning. The first shot didn’t hurt and I had few side effects (beyond a sore arm), but it’s the second shot that most people say will knock the daylights out of you. It’s the biggest sign that normalcy is in sight and if only for the sake of my disabled, chronically ill mother, getting the vaccine as soon as I could was a priority. I’ve gotten used to some aspects of our new shared isolated lives, such as not having to commute to work or physically deal with co-workers and supervisors. My job is flirting with the idea of returning us to the office “this summer at the earliest” and that may definitely take some adjusting for me. It’s been nice saving some $40 a week on transportation expenses, as well as money on getting snacks and lunches outside. On the other hand, it’s meant less walking and I definitely have gained weight, just as I am also getting older and my metabolism is slowing. At least physically. Mentally I am still as manic as ever.

On the other hand, this year has really drilled in that I am not getting any younger and while it is very lame to be a guy pushing 40 trying to make up for lost time, it may be even worse to not ever try. I have lamented endlessly about feeling cheated out of expected rites of passage or romantic milestones when young due to my own inferiorities and social expectations of men, and it remains a shame I never will enjoy the cheap, simple thrills of teenage or young adult romances. I’ll never have that much free time or fewer worries again. I’m not in my physical prime anymore. And my outlook on life has probably gotten less patient and bitter even if it doesn’t really show here. I’ve certainly become more short tempered over the last 2-3 years than ever, which is not good. I sometimes feel that it is a shame that my first and possibly only lover may not get me at my best, and my best was pretty crappy to begin with.

But, plenty of lamer, uglier, shorter, meaner, fatter, and balder men than me plunge into the dating world with delusions of grandeur, so why not me? I at least can admit to myself I don’t know a thing about pleasing a woman and being eager to learn. That alone may make me distinct for my age group. Most dudes my age or older who are single are very set in their ways and think they know everything. I KNOW I know nothing, and that can be key to learning. And nobody knows what kind of dating scene the post-Covid lockdown era will create. Will it make women more discerning and less willing to even grab coffee with someone until there is a lot of online courtship and a real feeling of mutual desire? Or will everyone be hornier than Bowser from Super Mario Brothers and be “down to ****” with anyone who at least seems reasonable and available? Or could it be a blend of both depending on the person? I certainly have chosen a hell of a time to consider jumping back into the dating pool for the first time in about a decade, but then again, my luck’s always been pretty terrible.

Dateless-Man vs. Hairlines

Speaking of age and bad luck, I have noticed my hairline is beginning to recede. Considering I am in my absolute late 30’s and at least 2/3rds of my male friends were at this point at least a decade sooner, I may not elicit much sympathy here. How many men aren’t at least starting to thin as they near 40? My maternal grandfather still had a full head of hair when he died in the 90’s, but it had also receded quite a bit. My father and his relatives have been absent and a mystery, but he may have been balding in the early 80’s, according to my mother.

Suffice it to say even with Covid restrictions, I have only had one haircut within the last year and change. I usually averaged 2-3 a year. I am deathly afraid of having hair cut which will now never grow back.

On top of everything else going on, I was not in the mood for a midlife crisis. I haven’t even gotten over half of my juvenile crises. I haven’t even kissed a woman on the lips and now I am shopping for hair loss products? My looks are average at best with hair; I am in no mood to have to consider dating as the Penguin’s stunt double. How is that even fair!? So I have been using some products, and the latest includes a full on laser light helmet. It kind of looks like something used on Power Rangers, only to combat baldness and not a giant rubber suited monster. I don’t even know if it will work and if it does, the results may be minimal or moot.

Now, I know what some people will say. There are plenty of balding, overweight guys who get laid; in fact some are studs and don’t have to be famous. But that usually relies on two things: confidence and personality. I have none of the former and barely a handful of the latter. I’m an inoffensive white guy who is neither tall nor short who has a sense of humor; in NY I am a dime a dozen. Battling evictions and Covid was bad enough; now my scalp is a ticking time bomb?

It can genuinely feel as if the fates that be do not want me to ever have sex or find love — or if I do, it has to be after overcoming what anyone could fairly describe as a well above average host of challenges. At least with someone who is not zonked out to their eyeballs in a nursing home. Why can’t they throw challenges at the buff college dudes who sleep their way through bars and throw me a bone just once? I jotted down my fairly reasonable dream date: I’m not asking for Jessica Alba emerging from a clam.

Dateless-Man vs. Fetish Writing Part 2 (or “Revenge of the Kink Panther”)

Finally, perhaps a bit of better news. If 2021 has had any theme to it so far, it’s been “The Age of Kink”. Two out of three posts were about fetish writing and one was that aforementioned “mildly erotic fantasy.” To summarize again, I’ve long admitted to having a fetish, but I’ve been too shy or embarrassed about it to reveal it even here, on my own blog. In contrast, my “older male virginity” has been the topic of at least a dozen entries over the years. It is something I genuinely feel is more taboo emotionally, even if objectively I know it isn’t that bad.

I post under another avatar at a message board dedicated to the kink and I had engaged in text based role play with two women regarding it since 2018. One of them messaged me at random to get that ball rolling, and it ended because she lied about being underage (at the time). I posted an “advertisement” about doing this on the forum and another woman messaged me about this and we did some text roleplay for about 10 days before she ghosted me. My last entry about this saw me casually mentioning whether or not I should just start writing outright fetish fiction on Deviantart.

Well, three weeks ago I did just that; I created a Deviantart profile based around my avatar on that message board and have just been writing some fan-fiction centered around the fetish (as well as reposted some old stuff I wrote in 2012-2013). I’ve written about 4 new stories within the last 3 or so weeks and while it has been an adjustment to my schedule I have basically just used it to fill slower periods between my non-fetish geek writing. And so far the results have been positive. The stories garner 800 to 2,000 views each and 4-25 “favorites” from viewers (“likes,” basically), and I have about 22 “watchers” (sort of like subscribers here). A few of them are pretty notable people within the community I was in. I’ve quickly developed a few fans in the comment sections. The biggest difference is that 99% of the readers and viewers are men, whereas before I was text role playing with women. I’ve hardly become a rock star but it could be argued that in only 3 weeks I am averaging as many or more viewers with my account there than here.

Admittedly I know I am probably writing “fap fuel” for dudes which is a bit different for me, honestly. But it has been good to express myself with a part of my sexuality which even I consider taboo and for it to have some positive result. It’s less reliant on the immediate reaction of another person like the text role playing is and it is something I can do at my own pace. It’s a safe and harmless way to express this fetish without exposing my real identity or being uncomfortable, which I think it a good thing. I do think some of the shame revolving around it is unhelpful in my attempts to gather the will to date again. I don’t intend to ever tell a woman about this IRL as myself, even if we were dating a while and she volunteered of her own volition at random that she was into it, and that’s fine. Nearly everyone has fantasies or whatnot that they never act on. If not, more people in real life would be superheroes, equestrians, or astronauts.

And no, I am not linking to my Deviantart page; the fetish is pretty darn obvious. And no, you won’t find it by searching Deviantart for “Datelessman” or some combination thereof. I’m hardly a rookie about creating alter egos. Nice try, though!

It feels good to be complimented and flattered about something at least tangibly related to my sexuality, even on a scale as small as this. I like the idea of my imagination being used and applied in some small way towards something less “innocent” in a space and way where it is acceptable. I don’t like using this word since as a straight white man I have more privileges in this world than I probably realize, but it is nice to feel some kind of “agency” about these kinds of things even in this small way. And thank goodness I live in an era where doing this is relatively easy; in the 80’s my best option would have been to try to get a job as a contributor to a sleazy fetish magazine or “newsletter”. One could say that it may not be helpful since Deviantart is mostly appealing to dudes and my issues revolve around women, but at the core, my own self doubts about who I am as a man and about my virginity and lack of experience are all concepts invented and enforced by men anyway.

TL:DR — I am getting vaccinated, fretting about a receding hairline, and am writing fetish fan fiction online semi-regularly now. What a time to be alive.

Thanks for reading. Once again, I remain the Dateless-Man.

The Kink Panther Strikes Out!?

As this blog nears its 7th year chronicling my thoughts (and memories) about my own romantic futility, it seems that certain periods display certain themes, whether intended or not. The beginning of the blog, from 2014 to about 2016, were focused on recounting memories and experiences I’d never told anyone or committed to paper, to release them from rattling around in my mind. 2017 was sort of a “year of Zen,” where I tried to achieve a state of no longer caring so much about being a lonely older virgin, or at least to convince myself to stop caring. 2018 began the “Age of Eviction” where my thoughts and feelings about my love life are always overshadowed by a far more pressing need to survive an endless eviction proceeding between myself, my elderly mother and a slumlord. This extended into 2020, which as we all know is the “Age of Covid-19,” which has not ended and all but eliminated, or at least heavily complicated, casual dating. Couples already married or cohabitating may be fornicating like rabbits, but any other kind of dating has been muted due to fear of the virus (and bringing it home to more vulnerable relatives) as well as venues to go to on dates (bars, clubs, restaurants, movie theaters, museums, etc.) being closed or having limited occupancy.

So what about 2021? The Covid-19 and Eviction stuff is still intertwined, but looking back at my content over the last few months, and it seems that I am seeking some limited exploration about my potential unresolved and unexplored kinky side.

To recap, I am a person of duality. Having only been on three dates (and three speed-dating events) in my entire life, I have potentially very outdated and juvenile views of romance and sex. The very concept of kissing seems like a forbidden zone since I have never done so. Things which most people have done as pre-teens still remain a realm of fantasy and conjecture to me. Not only have I never had sex, but I have never had a relationship before, which may arguably be a bigger red flag to a woman as a man in his extremely late 30’s. So my fantasies of kissing or even intercourse are milquetoast, missionary style basic stuff. Yet on the other hand I have a genuine fetish, which I have never revealed on this blog or to anyone. In contrast, there are a handful of people in my life (besides my mother) who know I am a virgin and I have bleated about it online either here or in other forums in miles of digital text. So I am someone who would have to work his way up to a 1950’s style malt shop sock hop that ended with, gasp, a kiss and some light petting, who also has a weird fetish somewhere. How I can be a bland inexperienced virgin with a fetish? I suppose people are full of duality, and perhaps as my situation becomes (or feels) more desperate, I am seeking to achieve some degree of resolution through my limited means and understanding.

My fetish is nothing illegal; at least not my personal interpretation of it. It does not involve animals or children. In fact, elements of it have been featured in media geared towards children, albeit not in the same context. In an objective, abstract sense I know that it isn’t terribly unusual, although I am not certain if it is as mainstream as a foot fetish (which I do not have). But in a personal sense it feels very taboo and disturbing, especially since when combined with my own virginal and antisocial profile it makes me seem more like a creep than I am. It’s possible to have some sympathy for an older male virgin and see a potential date or love making session with him as a case of finding an older man with the passion of a teenager. Considering how many men over 30 are dull, dispassionate, and selfish lovers, I can somewhat understand why some women may not be repulsed by the alternative (an undersexed repressed dude eager to slurp her all over). But throw in a fetish and suddenly I’m a villain from Law & Order: SVU or a direct-to-video cop flick. Or I match the profile of a spree shooter, which horrifies me.

I’ve dipped a toe into trying to explore this with another person before, albeit in an accidental way. As chronicled in The Kink Panther and its follow up, on a forum where I post other another avatar, a young woman contacted me at random and wanted to text role-play some sessions regarding our shared fetish. At the end of 2018 I learned that the young woman lied about her age and was younger than I’d realized. Our sessions were never romantic or sexual (despite her efforts at online flirting), merely related around fictional characters and text role play, akin to an interactive Choose Your Own Adventure. So, I decided, if I’d found one person at this forum by complete accident, why not create an “advertisement” for some text roleplay? I’d have a better shot of finding someone who wasn’t a minor that way.

So that’s what I did; in January I set up a topic at the forum describing the sort of text role-play I was seeking, some ground rules and so on. It was the closest I’d ever come to making a personal Craigslist ad. Text role playing is actually common at some online venues like Deviantart, or other forums. And I’d done text role playing within geeky universes for many years; they were just not centered around a fetish. And for a few weeks, there was nothing.

But then I got a bite, A woman (or at least an avatar identifying as female) who I will dub “LS” contacted me via the forum’s private message feature. She decided to take me up on my offer and for a week we just brainstormed various characters and situations to base the role play on. Then for another week we engaged in it, and it was a lot of fun. She, much like the young woman in 2018, appeared genuinely impressed by my imagination and ability to quickly craft narrative fiction. With a base premise and cast of characters I can easily type out dialogue and exposition and work with whatever the other person gives me in return. I sometimes remain baffled at how little it takes to impress people; stuff I consider a parlor trick. Again, nothing about our sessions was sexual; our characters didn’t have sex or kiss and that was not the agreed upon premise. It was strictly fetish related, or rather, an adventure which we both know will lead to it. It was great.

But after about 10 days, she said she would be busy with work and not be able to continue for “a few days.” That’s become about a month and a half and counting. I haven’t nagged or anything, knowing the golden rule that if someone drops online communication, you can send one further “hey, what happened” kind of message before you have to leave it up to fate. People at the forum do come and go at odd intervals (even regulars), but I can’t hold my breath. No one else really bit. The young woman who triggered this thing in 2018, who now would be 2 years older, also more or less said “hi” and we exchanged some small-talk messages but that was it.

Beyond doing some fiction on Deviantart somewhere (which is more time consuming and labor intensive), I think I’ve exhausted this low investment option. I suppose I did see a brief gain, since it was nice to try this sort of thing more deliberately rather than from some “rando” contacting me. I suppose I could finally admit my fetish here and use this space for such narratives, as I noted in January, but I am unsure if I want to see this space become lost entirely due to fetish fiction. I did do a narrative last month, sort of acting out what would be an ideal initial sexual experience and that was certainly interesting for me to imagine. In theory I could do that further if I admitted my fetish, but there is a part of me which is not ready or comfortable with doing this.

I don’t think it is necessary for me to admit what it is for me to advance in whatever my love life is or may be. There are plenty of people out there with fetishes or sexual fantasies who never act on them or admit them despite being married with children. It’s okay to have some secrets, although I don’t think it helps me to have so many. I have to hide my virginity, my romantic inexperience, my anxiety, and a fetish? That’s a lot to bottle while trying to be charming on a date. So I am doing my best to work through some of that as I go, and the fetish is clearly that last wall I don’t want to touch. I mean, I’ve typed circles around it without admitting what it is.

So it looks like the Kink Panther got ghosted. Where I go from here is unknown.

Our new president claims the vaccine for Covid-19 will be massively available by May, and life may start getting closer to normal by fall? That seems like a lifetime from now, but will come faster than I expect. If it does occur, will I finally, and belatedly, give dating one last chance? I don’t know. But I have a little time to sort that out, and work on myself.

Although eventually there is only so much I can learn without doing.

Thanks for reading, and for another month I remain…the Dateless-Man.

Dateless-Man vs. The Dream Date? A Fictional Interlude

Well, this may not be terribly erotic, but it will be different. And after nearly 7 years on this blog expression of futile romantic plight, different is in short supply. So join me, will you, as I go on a journey of self indulgence.


How do we meet? Well, if it’s a dream, it could be because we happened to meet in the street at pure random, and you happened to like how I smiled, or my eyes, or the cut of my jib. Or maybe because you know one of my friends, who decided to introduce us because they knew you’d be perfect for me. But, this is a romantic fantasy, not science fiction. So how about the way in which would be most comfortable for me as well as cater to my ego, since it wouldn’t rely on random luck, or a friend, or even you, to do the heavy lifting for me?

So, we meet via an online dating website. I join it and upload the few flattering pictures I have of me. I examine the publishing criteria and write the best bio I ever have. I am honest yet witty; creative yet concise (now you know this is a fantasy). I input my measurements, which are hardly the worst but not terribly flattering (while shaving off about ten pounds, as one does online). I come off as both imaginative yet hard working; funny yet appropriately serious. In other words, I achieve the dream; I come off as more appealing than the guy with the mirror selfie and the guy making duck lips in a sweatshirt. I am, simply, your above average single dude in his late 30’s. And in the world of my dreams, being considered above average is all I could ever hope to be. I am a B+ Man and I know how to flaunt it. Heck, I am even honest about living with my handicapped mother, and because this is the world of my dreams, this comes off as a quality of tenderness instead of evidence that I am immature or broke.

And then we make our first interaction. My profile is barely up twenty-four hours when you instant message me. You give me five stars out of five. You give me a brief yet flirty greeting, perhaps mirroring that famous line by Mary Jane Watson: “Hey tiger, you just hit the jackpot.”

I read your own bio with bated breath, not quite believing I have gotten so lucky so soon even in my own dream. Of course you are physically my type, and I yours. But our bios are compatible, too. You have a professional job within the arts; perhaps as an editor of a major book publisher’s graphic novel division. You list similar interests in comic books, anime, media, and so on as I do. You also volunteer on occasion and above all, stress that you are looking for a sensitive man who can make you laugh more than one with abs of steel, a hypnotic smile, or a six figure bank account. You are down to Earth and value the little things and the tender moments more than big spectacles. You care more about an intoxicating brunch more than a star studded night on the town. And because this is my dream date, you even boldly proclaim that you have always wondered what it would be like to be able to take charge in the bedroom and groom a man not so “traveled.”

“Hey there yourself. Love the Spider-Man reference. Want to swing somewhere for coffee or your beverage of choice?” This is what I text back after perhaps an hour of hand ringing and anxiety about having gotten so lucky so quick. This is as clever as I can be in such a circumstance. Even in a dream, I am in a state of disbelief. But, you are patient and eager to meet the man behind the profile. You quickly agree and suggest a trendy yet inexpensive local place within the city which has both indoor and outdoor seating for the upcoming Friday evening.

For the days leading up to our meeting, I am a mixture of emotions and clashing thoughts in the vague shape of a man. I am excited that my bio has worked so well, yet terrified that I am somehow far more charming than I realized. I am giddy that a date with a woman who is so compatible in looks and interests happened so quickly and easily, yet also anxious that such fortune rarely comes without a price to pay. There is an extra spring in my step, more of a hint of a smile in my voice, and more of a sense of fulfillment and energy to my soul. At least for a week, I am no longer the Dateless-Man. I am a man with a date and a chance.

Yet there is also a tremendous pressure, despite my best intentions. I tell myself that this is only a first date, and that anything can happen. I insist that even if things don’t go well, the very fact I got a “bite” so quick proves I can be appealing and the effort was worth it. And I try to tell myself that this is only the beginning, and I should not pin all of my hopes and ambitions for an unfulfilled romantic life on this one seemingly perfect sounding date with a professional geek-girl. Unfortunately, despite all of my experience in sales, the one person I have never been able to “pitch” is myself. And as much as I try to tell myself to relax and play things cool, I also tell myself that I cannot afford to botch thing like I did all three of my other dates.

It is my dream date with my dream woman, and I am both eager and petrified.


So it is finally time for us to meet in that outdoor table at that local, trendy eatery. This naturally in a setting with seasonable weather and no Covid-19, which already sounds closer to a science fiction premise now than it should. I’m properly groomed and dressed, and since this is a dream date, I would be wearing one of my nerdy t-shirts under a sports jacket and some nice jeans, and this would be considered dress appropriate since this is supposed to be semi-casual, not formal.

You arrive wearing a nice jacket and appropriate top, a short skirt and boots. We actually both arrive at the same time, for maximum irony as well as because I can be impatient sometimes. We both have a good laugh about it as it turns out we were both on the same train, several cars apart. Some might call it a “meet cute” moment. We each order a drink and some food and begin our date. Like many dates it begins with some obligatory small talk. Just to confirm some of the information from our profiles and so forth. No one is really interested in it but it’s much commercials before a movie in a theatre. It can’t be skipped so let’s just grit our teeth and move on.

Once that is dispensed with, you get into some more meaty conversations with me, and since you are an intelligent and sassy dream woman, this also means you’re able to break the fourth wall quite a bit.

“My name’s Fantasia, which of course means ‘fantasy’ in Italian,” you say as you sip your drink through a straw, which I notice since it means an excuse to focus on your lips for a moment. “It’s not bad as far as names go.”

“Thanks,” I answer. “I was hard pressed for a while.”

“For a dream girl, I’ve noticed you really haven’t focused much on my physical looks,” you continue with a raised eyebrow. “I mean most guys would focus on my hair color, eyes, skin type, blah blah. This is a fantasy, you can’t be that partisan deep down, right?”

“Well,” I reply as I shift in my seat. “I can’t say I have that rigid a type. It’s not like I am only chasing after white women, or Asians, or so on. I could care less about hair color or so on. Many different types of women are attractive to me. I’m very flexible.”

“I’ll be the judge of that later on,” you tease with a wink. “But just so I’m not an amorphous blob in a skirt and sexy boots, is it okay if we just settle on some visuals? How about me being mixed race so I’m a little tan, with brown eyes. And I know you’re not hung up on hair color, I know you like more unusual dye jobs a little more than, say, blonde or brown. Right?”

“Um, yeah,” I reply, a little surprised. “But it’s not like someone who’s a brunette or whatever is a deal-breaker.”

“Of course not. So we’ll say I have black hair and some roots are showing but I died it purple, and it matches my lipstick and fingernails, alright, sweetie?” you state back. “I mean it’s your dream date, you don’t need a disclaimer on it, right?”

“Right, I guess,” I say back.

“I think it says a lot that this is your dream date and I’m kind of taking charge here,” you say, as you look down at your own body. “I’ve noticed I am a little voluptuous without being too lean. In fact Cosmo might say I should lose five or ten pounds but I don’t agree and neither do you.”

“Who really takes Cosmo that seriously, anyway?” I reply. “That is an awesome skirt, where did you get it?”

“Do you really care or are you just running with advice you read that said to compliment a woman on something other than looks so you don’t seem shallow?” You tilt your head and smirk.

I shrug. “Both?”

“Good answer. I got it on sale at this cool boutique I know,” you respond quickly to get it out of the way before moving on. “I also find it interesting that we share some interests but you didn’t just mirror all the stuff you like. Just at random I like Doctor Who, Sailor Moon and horror movies and you’re not especially wild about either. Why?”

“Someone who just mirrors me on everything isn’t a dream woman, it would get boring,” I reply bluntly. “I’m game to try some new thing so long as she willing to, too. Or even if she’s not. Maybe my willingness would rub off.”

You take a few moments to nibble your food as I do. “You’re pretty idealistic for a cynic.”

“Most cynics are frustrated idealists, ” I counter. “But this is becoming all about me. Your job sounds fascinating. I’ve love to hear more about it.”

“It’s one part creative and two parts hectic and full of deadlines. I have so many manuscripts to approve and edit, and then I have to contact the creators, and then help with the ad campaign for the books,” you answer excitedly. “But it’s all worth it to be on the cutting room floor of some great, fun stuff. I can be there to help nurture media for a new generation, and make it more diverse, y’know? Have you ever read YA comics?”

I nod. “Actually, yeah. I used to get review copies from a big publisher and I’ve reviewed a lot of them. I haven’t read one which was outright terrible.”

“That’s because they have better editors,” you say proudly. “And it has to appeal to more than old guys.”

“Yeah, definitely,” I reply. “I love seeing your passion about it.”

“You sure you want this kind of conversation on your dream date?” you ask, a bit curiously.

“Sure,” I reply with a shrug. “I like getting along with small talk. This is a dream date, not pornography.”

“Touche,” you respond as you finish your meal. “I just wonder if you want to skip ahead a little, is all.”

“Skip ahea–” It finally dawns on me. “We could do a montage. Is that okay with you?”

“Sure,” you say back before snickering. “It’s my first montage. Be gentle.”

We finish the rest of our food and drinks, and even have some desert. We finish our stimulating conversation about our work and hobbies, as well as other random assorted topics, such as gripes about mass transit. Both of us decide to go to a nearby bar for some more drinks, and to spend more time together. Neither one of us drink much, but nursing one or two drinks over the course of hours with food is fine. I am content nursing some general beer, such as Rolling Rock (TM), while you prefer a martini. I decide to introduce you to a bar which also specializes in arcade games that I went to once for a friend’s birthday party that I really enjoyed. You agree and after spending a few moments on your iPhone for directions, we walk several blocks to get there. We are so engrossed in our conversation that I barely notice you wrap your arm around mine and hold my hand.

When I do notice this, though, a tingling sensation rolls up my limb. I’ve never experienced this before, but I know I like it. The warmth and closeness to you makes me feel a happiness which I can’t quite explain. It increases the pressure to not mess this up, and I am trying not to showcase how giddy I am too much, since I always try to be aloof and cooler than I really am. Once at the bar, we both walk together with our drinks and examine the selection of arcade classics. Neither one of us are hardcore gamers, but both of us remember these quarter-eaters from our youth. I introduce you to three of my favorites from this location: X-Men Arcade, TMNT Arcade, and the rare Konami gem, The Simpsons Arcade. X-Men, in particular, I played a lot during my wasted youth in the 90’s and I know inside and out, which slightly impresses you. You enjoy some of the shooters, as well as Rampage and Street Fighter II. We spend a few hours there and many quarters, and we are both buzzing with shared proximity and nostalgia when we hit the street again. By now it is later in the night and the city is glistening with its lights.

“How was that?” I ask.

“Fun. A little geeky but I like that,” you answer back. “Hey, it’s getting late. Do you want to, um…”

“Uh, hang out more?” I smile and try not to show my anxiety. “Right?”

“Yes,” you answer confidently. “My place isn’t very far. I’m trusting you not to be an serial killer, okay?”

“This has already been the best first date of my life, so there’s no pressure. We can wait until another date or two for that if you’re more comfortable,” I offer. After all, I’ve waited over three and a half decades for this moment; another few dates or even a month or two is nothing more than an interlude.

“That’s sweet, I appreciate your disclaimer!” You chuckle, before patting me on the shoulder and winking. “But this is my dream date too, remember?”

“Of course. No pressure, right?” I smile a little awkwardly.

You continue to snuggle up against my arm and draw my face to yours. “None. C’mere.”

“Oh!” I gasp, as our lips draw closer.

The sensation of our lips connecting is another new one for me. It’s a first kiss so I keep things simple. I try to match your movements with my mouth, and share your embrace. For a moment I forget how I hated public displays of affection when friends or other people did them. Turns out it wasn’t just me be shy and was all about me being envious. Who knew? Me, deep down. I cup my hands on your cheeks as we kiss again, our noses side by side against each other. It feels so natural despite my eyes being closed for half of it. I can feel my own heartbeat increase and I actually think yours does, too. An actual woman feeling passionate about me for a moment? I never thought this was possible.

When our lips finally part, I have no idea how many minutes it’s been. We each take a moment to catch our breath, as your face is still cupped by my hands, and you stroke my hair a bit.

“I think we really need to get to my apartment,” you say in a soft and hurried tone.

“Yeah,” is all I can say as we walk, fast enough for it to be a near jog, down three avenue blocks and about four short short blocks to your apartment. Our hands are interlocked the entire time.

As an editor for a major book publisher, you actually earn a higher salary than I do. While hardly rich, it does mean that you live in an apartment building which is far more upscale than mine, with a doorman. However, you lead me to a back entrance that you also have the key for, which is a service entrance.

“I don’t need any side eye from the night watchman,” you tease.

It leads me to believe I am hardly your first one date conquest, and perhaps not the last. This hardly relieves my inner anxiety, but it helps me understand how you have been so quick to all this. You will know your body and best advise me on how to please it. We all but scamper to the elevator, which is empty as this is the ground floor and it is late at night. You hit the button to your floor as instinct before I even notice the doors closing, and then you are upon me for another embrace. This time our kiss is more exploratory; I feel your tongue touching my lips and while this does feel strange, I also know to reciprocate (or to at least try to). As always, my golden rule is to err on the side of gentle. We caress each other’s faces as the elevator moves, and my head bumps the wall of the car enough to make a sound.

You chuckle. “Sorry, you okay?”

I chuckle back. “S’okay, it’s good to know I’m not dreaming.”

“No, just typing,” you tease, as if the fourth wall were merely your plaything.

The elevator finally reaches your floor and we walk together to your front door. You have a keychain that features an exaggerated rendition of Luna the cat from Sailor Moon, which jiggles as you turn the key. Your apartment is cozy without being small; a large couch in the living room, a modest kitchen, and a fairly large “master bedroom.” The walls are painted a dark shade of purple with much of the furniture being leather bound. Several posters of rock bands and some films are in the bedroom.

“Nice place,” I comment. “Though if I’m honest I wouldn’t care if you lived in Scooby’s doghouse at this point. I mean, he even had a wine cellar somehow.”

“Dork,” you tease as you push on my chest with your finger to lead me to the bedroom. “We’ve both been out for hours, we need a quick shower. You first and then you’ll wait for me. Don’t take too long, stud.”

“Yes, ma’am,” I find myself saying automatically, a leftover from my call center job when I am not thinking clearly.

It feels bewildering, showering in another person’s apartment. But in the end, a shower is a shower and shampoo is the same even if it’s a different brand. I still make sure to lock the door behind me, perhaps as a leftover from seeing the film “PSYCHO” at a young age. I give myself a complete scrubbing, taking roughly 15-20 minutes. Out of instinct I partially redress, only without my shoes or putting my jacket back on. I had hoped the shower would calm my nerves, but it doesn’t. I step out of the bathroom and you are there with your towel and robe folded in your hands to jump in after me, giving me a quick peck on the cheek as we pass. Your room is darkened, but lit with a lava lamp and a scented candle. As you shower, I cannot help but pace across the floor for several minutes.

Do I tell you my secret? Even if you already know, is that a conversation I want to have on a dream date? How about my fetish? Is that also something I want to get into so soon? It is all happening so fast that my head is swimming. It is everything I wanted so far, and within a few moments my secret will be moot. I need to try to relax, and–

That is when I see a pair of eyes peeking at me from the doorway. They belong to a housecat; with black and white fur. You hadn’t told me about a pet, and I’d neglected to ask. I theorize that the feline had been in another room which I hadn’t visited yet, such as the kitchen (where the food likely is). Or, the cat had been elsewhere, perhaps under or beside the couch. At any rate, even though I haven’t owned a cat since childhood, I know how to greet one. I lower my palm to the feline’s eye level and make a motioning gesture with my fingers. It works most of the time and sure enough, the cat comes walking over and gives my fingers a good sniff. It begins to rub its face against my palm for a few passes and offers a soft “meow” up at me. I offer a pet across the lower neck and back. It turns out the feline is friendly and quickly bounds beside me on the bed for more.

After a few minutes I hear your voice in the room again. “I see you found Smithers. Or he found you. I wasn’t sure about saying anything because a lot of guys I bring here don’t like cats.”

“I love cats,” I reply as I turn back to you, clad in only a robe which is barely closed. “There’s a joke about a pussy and me playing with it that I could make, but I won’t.”

“I think you just did,” you say as you slink closer.

“Smithers,” I say, once again falling on a reference. “After Veronica’s butler from Archie?”

“You don’t miss anything, do you?” You chuckle. “Good. I like a man with attention to detail.”

A pause, as you play with the collar of your robe.

“So, are we going to undress, or do we need to play some strip poker?” you ask gleefully.

“We’d better undress. I can barely play blackjack, much less poker,” I answer as is hesitate before pulling my shirt over my head.

I’ve never disrobed in front of anyone, at least not since I was a child. I only see the flaws about my own body, especially my torso, back, and stomach. I remain silent, not wanting to ruin the moment with my own anxiety.

“Hey, it’s okay,” you say as you toss your robe on the bed, which also causes Smithers to jump away. “See, I’m not exactly an American Gladiator either.”

“Nice reference,” I say with a smirk; nothing calms me more than geek stuff. “You’re beautiful, though. I’m–“

You place a finger over my lips as you crawl onto the bed. “We’re here, no more self doubt, huh? Guys who obsess over their own bodies neglect mine a lot. Just go with the flow.”

“Right.” As you proceed to kiss me again, I undo my pants. A part of me regrets wearing them now, since it’s hard to concentrate on doing both at once. I wonder how musicians handle it so easily? Hell, many of them do that in a moving vehicle, to boot!

I ask if you want a back massage, and you agree. Now this is something I have done, albeit not with a stranger. Again adhering to err on the side of gentleness, Your back feels smooth as silk, and it is amazing to even touch another woman here. Every positive sound and motion you make fills my soul with anticipation. You reciprocate, and comment on how “stiff” I am. I am not sure if you mean my back or somewhere else, and I don’t care. You are the one who starts to shift your caressing to below my waist, and I get nervous for a moment. You ask if it is okay and I nod, asking if I may touch you as well.

I decide not to tell you of my virginity, or of my fetish. I am anxious enough and I just want to enjoy the experience and do as well as I can with it. This is my first time and I want to explore. I gently go from kissing you on the lips before moving onto your lips. I gently caress your breasts, gently and softly, treating them as delicate pleasure zones. I move my fingers down the sides of your torso, and am simply enjoying the sensation of touching a woman. You tell me that I am going to drive you crazy if I don’t start going somewhere lower. This is my first time seeing a vagina in real life and while I have certainly seen pictures and diagrams, they do not compare. My heart is beating so quickly with anticipation and excitement mixed with fear that I worry about vibrating through the floor. So with no other options or experience I resort to asking a question. As always, I try to use humor as a mixer, but I do not know if it will work.

“This is sex by numbers and I’m the brush; just show me the numbers, baby,” is the best I can do on such notice.

Its lame; bad porn writing. It’s the biggest moment of my life and that’s the best I can do. But this is a dream date, so it’s good enough for you and you begin to guide my hands. Once again, I begin with soft and gentle strokes, as if caressing a flower. When you want it firmer and harder, I do so. I do my best to not go too firm too soon with my hands. By now, my own genitals are throbbing, but I am not in a rush. My orgasm is pretty much guaranteed; I’ve made myself cum rubbing off against furniture or the side of my own leg. I did not wait over thirty years to rush things now. In fact, if I could relive one moment endlessly for the rest of my life, it may be this one, or this date.

In time you become wet, and then I ask if you are ready or if you want more. After some more caressing of your sides, you nod and motion for me to initiate. I fumble for the condom I would have brought, as I always do for every first date. I try to open the thing and roll it on as fast as I can; I am thankfully I did not have to undo a bra tonight. After so much anticipation, it feels as if my manhood is about to fly through the roof, much less enter such a wonderful woman. Once more, I begin gently, only increasing pressure when guided too. By now I have confidence to ask, if only in one word questions.

It is nothing like masturbation, and not because of the physical sensation itself. The evening leading up to it, the conversation, the laughter, and the pure happiness…there is no self session which can match that. Your body is a living pleasure zone and I practically want to touch every inch of it. It feels so warm, but not uncomfortably so. And after it is finished, if you are up for it, I return to caressing your body where you want it. I have never tested my erections for distance but I know I can return to rigidity with some more stimulation, and your entire being is stimulating. Time blurs. The clock does not exist. I may forget my own name at some point. None of that matters. What matters is the two of us in this bed, having sexual fun until we both are about ready to pass out from pure sexual ecstasy.

Even when it is over, I want to be close and together with you as we sleep together — actual sleep. My last thoughts are that this is all I have ever wanted since I was about 16 or 17 years old, and that after so long I have finally achieved it. I am no longer a virgin, and no longer the Dateless-Man. In fact I don’t know what I am now. And while there may likely be a twinge of regret for not getting there sooner, I am satisfied that I got there with you, in this way, tonight.

And I hope to take this journey with you again another evening, and an evening after that, as we continue exploring what our lives are like together. At least for a little while, so long as we are both happy together.

I try not to think about Smithers watching the entire thing.


So, that’s it. A completely fictional, mildly erotic and completely amateurish account of what I would like my first romantic experience to be, under completely ideal and optimal circumstances (not realistic circumstances). There is a bit of a bittersweet taste to it, as I suspect I may never experience anything close to this. It is a pandemic era, I am fighting an eviction, and age is against me. And considering all that, there are worse things than never having sex. Being homeless or either dead or disabled from Covid-19, or heck, a speeding car, are worse.

But a fantasy has to start somewhere, so this is it. I want to meet someone wonderful, who is at least half as into me as I am into her, and I get her off as she gets me off. That’s it. I don’t need the moon. I never did. Am I really asking for so much? Is it really so difficult? It has for me. The perfect set of circumstances has never fallen into place to make the above anything less than a lonely man’s fantasy.

It’s not a bad fantasy, though.

For another month, I remain the Dateless-Man. Thanks for reading.