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.
10 THINGS DATELESS-MAN WILL NOT DO TO HAVE SEX:
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.