International Sucks If You’re Single Day

“I’m just a lonely boy, lonely and blue. I’m all alone, with nothing to do. I’ve got everything you could think of. But all I want is someone to love.” — Paul Anka, “Lonely Boy”, 1959.

Don’t let the quote fool you. Valentine’s Day came and went and I wasn’t too blue. The period of time from October to March usually represented the half of the year when I got more depressed, morose or lethargic. I’m hardly the only one who experienced this, and studies have shown that the change of season often have that effect on people — less daylight hours. As I explained once before, it starts in October because Halloween represents a holiday I used to love as a kid but has become less enjoyable as an adult. Christmas has tons of false commercial cheer and New Year’s tends to bring regrets. February brings “International Sucks If You’re Single Day”. And my birthday is in March — where I grow another year older as what I am.

When I started this blog in 2014 it was right before this period and I am sure some of my posts during it showcase it. Not only did I intend this blog as an outlet for my memories and frustrations regarding whatever anyone could call my love life, I also intended it as a bit of a self experience. I had never typed up any sort of journal expressing my own thoughts on personal, non geek or genre related stuff in my life. I had no idea how I would react.

So this is the third annual go around of this “period of the year”. And beyond one period of frustration, I’ve been pretty “chill”. Recent reorganizations at work have kept my mind elsewhere, but I don’t think it is just that. Having this space to not only be able to vent, but to have some discussion or reflection after with others — albeit on my terms, since this is my blog — has helped. I’m not saying when the big 2/14 came around I was dancing in the street. Least of all because recent snows have kept the streets slick and ice ridden. But on the whole I was okay.

And anyone who has ever taken mass transit in a major city after February 14th can tell you, it can be a gauntlet if you’re in the wrong kind of mood. I work atypical hours so I usually come home later than usual. As in, around 9-10 p.m. That is after the period where couples who work can still meet after and do whatever. And boy, the couples were out in force. I didn’t witness any platform canoodling but there were plenty of flowers, balloons, couples just drinking in each other’s company. Being that I live in NY, these were couples of various types of people and orientations as one melting pot. One couple that were standing on the train for a while looked to be in their early to mid 40’s at least. The woman resembled Nancy Allen to me (of Robocop and Carrie fame). Since whenever I often see couples either making out or soaking in their time together, they tend to be younger, I actually thought it was cool to see a couple who were neither elderly nor college age.

As also part of my usual tradition, I got some a card and a small gift for my mother. It’s kind of lame that she’s really the only person I ever had to shop for on that day. I’ve sort of adapted it to being another time I have to buy her a present and a card out of the year. It isn’t that I dislike it or anything, it’s just something I compartmentalize in my mind. I barely even like mentioning it because of “Momma’s Boy” stereotypes that I have always felt surround me. Only in America are adults who live with family members and/or parents seen as immature or lessor than. For most people it is an economic necessity too, which also implies bad things. Her being handicapped of course complicates it, but most people don’t care, frankly. The American model is to abandon all of your roots as soon as you can, live alone, work for some corporate master, earn 10% of your worth, retire on 10% of that, and die. Hopefully after breeding at least once. It all seems so small and mechanical to me. Especially as plenty of super rich families all live close by or under one McMansion here like on Dallas. But I digress.

Regardless, I took an “International Sucks If You’re Single Day” without any real period of being glum as a good, albeit different thing. It is more evidence to the possibility that after so many years, I am finally accepting my status on an emotional and spiritual level. Perhaps having a safe place to vent on my own terms really was a missing component. Sure, there are times when I may feel a twinge of frustration or longing, but I don’t sense they’re as long or frequent as 2014 or 2015. We’ll see how I handle my birthday, which I always dread. I never want to be another year “past 30”. Enough of those and I’ll eventually be “past 40” and so on. If I hate living up to plenty of stereotypes of virgin men (I’m a geek, I live with my mother, I don’t have much money, etc.), imagine when I am a literal 40-Year-Old-Virgin. Being a working adult helps with that; I can keep my birthday on the down low, have a normal day at work, and be done with it as soon as possible. That’s exactly how I like it. After all, what is the point of a celebration to me? What sort of life do I have to celebrate? Sure, I have it better than a lot of people and I do try to appreciate that. But on American, NY terms I’m not even a face in the crowd. I’m on the lowest rung out of all of my friends. I am behind them and most of my peers economically and romantically. Why would I enjoy celebrating more of that? Just give me a normal day, thank you. That was always harder at school, where teachers and/or friends would insist on bringing it up every year. Plus, teenagers and adults in their 20’s always want to get plastered on birthdays.

I wonder if part of the acceptance within me, besides the sheer venting, is the recollection and listing of all of my past memorable incidents with women or futile romantic efforts. Actually laying them all out in text form from A to Z in rough chronological order has allowed me to go back at them beyond just my own memories. It was a release of some pressure, perhaps. Or maybe seeing it all in black and white helped me come to a place close to acceptance. I am what I am, and certain things were never meant to be. Fighting against this, hoping against hope, yearning for things I was not made to attract brought me a lot of pain. But now I have it all here, to read and reread if I need to. It is easier to finds a new angle on something. In addition, it’s easier to not have to recollect it as often, since I have it down in text here.

It could be argued that if I really accepted my state, I would reveal more of myself. I would reveal my virginity in my public profile or at least be willing to admit my exact age, name or where in NY I live. I wouldn’t hide my virginity to others or avoid the subject entirely. I would argue that while I may be closer to acceptance, I am not 100% of the way there, and even if I were, relapses or regrets are part of being human. I don’t like being judged, or pitied, and revealing those things openly would result in both. I don’t want to become a laughing stock at work. I don’t want to have some of my friends who are women pity me or misunderstand me. Being aware of public perceptions is part of acceptance. What I am is not normal. It never will be. I have lost too much time. Using the mantle of the Dateless-Man suits my purposes for now. I can vent and share without being judged or pitied on too personal a level, and I compartmentalize this from my “public” life a little. I am not ready to reveal myself as a freak quite yet. I am not ready for many awkward conversations about it. I barely even like to acknowledge it verbally.

At any rate, at least now is “Happy Cheap Chocolate Day”! Corporate candy overstock is my best friend.


Dateless-Man vs. “Carrie’s” Birthday Party

So, it’s officially 2017. A new year, new possibilities and the same old worries. The minimum wage has gone up in NY, which has led to downsizes at my job. I’m safe, deeply entrenched, for now. America has a new President and my birthday is only two months away (give or take). It will be another year as Dateless-Man, and another year of older male virginity. Having exhausted most of the recollections of my interactions with women, at least those worth typing a few hundred words about, over the last two plus years, topics for posts sometimes get scarce beyond my sporadic whining about stuff. But, this weekend was an exception!

Long time readers may recall the last time I mentioned a woman I dubbed “Carrie” last February. The long and short of it is that she’s the ex of one of my friends from maybe a decade ago who I later realized I had an awkward “2nd Base Moment” during that tenure. Basically, during the time they were dating, she was at one of my pal’s BBQ’s, got falling down drunk, and in trying to catch her from face-planting on a porch the side of my hand brushed against her chest. I apologized to her, and my pal, frantically, everyone laughed, great times (for them; I was mortified for an hour). We got reacquainted on Facebook last year as she went thru a bout of depression. Eventually she got better as she met a new beau, and life moved on. Last week was her birthday and she invited a bunch of people to a party over the weekend. I was invited; in fact, I was the only member of my usual “crew” (who I barely see anymore) who was.

At first I debated going. The party was held in two places; a classy pizza place/Italian restaurant and then at a bar which was loosely themed around Dr. Who. “Carrie” was the only person I would know at the party, for one. The bar was also fairly far from home, for another. And then there was my general dislike for parties. But there were other advantages. I had nothing else going on, for one. Another was that while we’d chatted online, I hadn’t personally seen Carrie beyond a quick “hi-bye” at some previous bar shindig years earlier. And I won’t lie; having something to post about here was maybe 20% of it.

The rest was my mixed emotions regarding her. Carrie had been seeing a guy as of last year, but in recent months I noticed a change in her online feeds. Less happy pictures with him, more seeming to acknowledge being single. Some angst about hitting another year in her 30’s unmarried and without kids. On the one hand, we are going in different directions romantically; she wants to settle down with something long term, and I’ve not even begun. She also doesn’t know about my secret and it’s embarrassing enough with a woman I haven’t known long, much less one I have probably known loosely for almost a decade. On the other hand, I won’t lie and say that maybe 2% of me was curious if she would give me some “signal” at the party. I knew better than to unload emotional vomit towards her at her birthday party. As it was, whatever angst from last year is over for me. I moved on emotionally, but am fine with being pals. Since her social circle was new to me, I was also curious as to any possibilities of any of them including single women as well as general networking.

So I got a hair cut, shaved, and put on nice but still semi-casual attire. It was appropriately dressed for the shindig as I got to the restaurant later than some but earlier than roughly half her guests. Carrie seemed genuinely surprised and pleased that I had made it out. I have a reputation of being a bit of a hermit in our social network. She naturally had to move about to different sections of the table as more folks arrived. I chatted with some of the other people there, who were either single dudes or paired up couples. The party in the restaurant was fairly intimate, only about a dozen or so people around some tables. The pizza was okay, gourmet and all that (i.e. light and flaky). There was one older woman who was maybe in her late 30’s or early 40’s who I actually would have liked to chat with, but she wasn’t there long and spent much of her time with Carrie. Overall, at least I thought I handled myself well. There was no noise to drown anything out, and I kept people laughing with one liners or banter about whatever topic it was (usually shared media we liked). I didn’t hog Carrie’s attention and there were moments when I had to “recharge”. But I doubt if anyone there who didn’t know me would have known I was shy and introverted.

Two of the couples there were heavily into gaming and other nerdery. They bonded a little over having Dungeons & Dragons days per week and playing other games. One couple I talked to extensively; oddly I seemed to get along well with a perky blonde who was with an ex-soldier turned snowboarder and thrill seeker. They wore matching tuxedos, but she decided to wear his top hat, so she was like a blonde Zatanna. It was delightfully weird. It also made me think about how being into nerd things seemed to be no big deal compared to my college days. The couples talked about nights playing intense board games like old school couples used to talk about poker or bridge. It made me wonder what it would be like to have a lover who shared my passion for something.

Once we got to the bar, however, I’d say my social interaction deteriorated drastically. It was insanely loud and packed; barely standing room only. It also had live music, in particular a swing band whose specialty was playing “swing” versions of mainstream rock or pop songs and mixing them together into movements. It reminded me of The Mask and my fascination with that film and animated franchise in junior high. Hell, I related so much to the Mask as a tween that it alone may be worth an article. It was a great band, but it added to my feeling of isolation. Some of the people were dancing in the front, which only reminded me of my inability to do so.

There are three reasons why I don’t dance. The first is I have no skill. The second is that I have no rhythm. The third is that I am too uptight to humiliate myself trying. I didn’t used to be; in elementary school during my class clown, pre-bullying days I went to some of the dances the school started holding in the church basement by about 4th or 5th grade and didn’t mind flopping around like a dingus. But then again I also had plenty of pals to chat with between movements. Nowadays I am far too sheltered and closeted to even try to do so. I sometimes wonder if I would were I wearing some disguise and there was no risk of identification. Unleash my inner dance comedian (because that is how badly I dance; it invokes laughter, but when I am the right mood I actually don’t mind performing for laughter). Sort of like a park mascot or…The Mask. Some of the people had some skill (the women more than the men, naturally), but a lot of it involves just letting go and moving to the beat, and I can do neither.

Carrie danced. At one point she rubbed up against one of her other, taller, guy friends who she was very familiar with for an extended period. She wore a rainbow sparkled dress thing and had dyed her hair red. She sometimes laments about being a size 8 or 10 or whatever but it’s all proportioned. Besides, anyone who isn’t sleaze would consider that “fat”. It sounds lame, but sometimes I simply enjoy being around a woman I consider beautiful even if it’s totally platonic. It makes me feel good, in a non lustful way, to be in her presence. To be worthy of her presence. Maybe it is inexperience, or prolonged years of being unworthy or beneath the notice of women I desired or was attracted to or even got along with. I tried not to huddle around her too awkwardly, but the noise and dancing made it hard to chat with anyone for longer than a few lines. There were 2-3 other women there who were Carrie’s friends, but it was too loud for introductions and I was neither confident nor loud enough to introduce myself. I felt it awkward or risking being “obvious” to loudly try to introduce myself to them at a bustling bar without any prompts. Two were in corsets. Carrie has some very unique friends. Maybe that’s my problem, I was the only one of my crew who stayed weird. They all morphed into normal guys after college, and I remained an awkward freak.

I would watch the dancing, the overall going with the beat, and would try to calculate imitating it like a robot. Like most bar experiences, it made me feel left out, like an alien watching humanity and trying to imitate from afar. At one point Carrie noticed and asked, “Too social for you?” I replied, “No,” which was maybe half a lie. The restaurant was fine, but at the bar I was overwhelmed. I wondered if I could handle parties or even dating again, so long as we avoided being lost at a bar. I wasn’t the first to leave, but after the band left around midnight people started filing out, and I didn’t want to miss the last bus out of town. As it was, I barely made it. Carrie once again noted being pleased that I made it out, which she followed up on via Facebook.

I imagined that had this party happened maybe ten years ago, or even 8, I might have reacted differently. My reason for going would have been 100% hoping Carrie initiated “something” rather than acknowledging that we were on different paths. I would have sulked or been jealous about the geek couples I wasn’t part of. It would have depressed me later. Instead I am calm, collected. I acknowledged it all and enjoyed what I could. Carrie did inquire about her ex who was my pal, since he’s quit social media for at least a year. We also chatted about other friends who will soon be parents. Carrie expressed surprise that they would be the first in our group to breed, since she considered most of them “immature”. I joked that most men’s emotional maturity is at best half their physical age, so they were on track.

Overall, it was an interesting experience for me. It reaffirmed my inability to cope in loud bars or massive groups socially. In more intimate settings, I imagine that I joke around enough that people might not know I was shy and introverted unless they knew me well. One half of the evening allowed me to become a part of a group of mostly strangers, and the other half reaffirmed how in many ways I am an alien on my own planet. I will never relax enough to dance, and I always feel apart from people in too large a group at clubs or bars. Carrie obviously made no “moves” towards me and if anything, rubbed up against another guy literally in my presence. There were at least 3-4 other women I encountered that I would have liked to get to know better who for aforementioned reasons I never said a word to. Yet there were no feelings of malaise or regret to this shindig for me. Maybe in a way this was also part of why I went. To see how I would react should things develop in the way I expected them to. C’mon, I’m too experienced to assume that Carrie would reveal some secret desire or I’d bump into another woman who was into me. I’m not a teenager or in my 20’s anymore. I know that’s not meant to be, and doesn’t happen at social settings for me.

And I was okay. I wasn’t skipping down the street about it, but I was okay. It was water off a duck’s back, a fact of life I had accepted. I was more concerned at the end with catching my bus and making it home without being involved in a drive by. Is it possible I am coming closer to my Zen? I’ve lamented many times how I wished that my inner desires for companionship and love would vacate my body. How I could wish to somehow reach into my soul and turn that desire off like a switch, through willpower alone. And sure, there are moments still of frustration and envy. Unfortunately, I am only human. But overall I think I am in a different place now than I was at the end of my 20’s, or even in 2014 when I began the blog. Having this as a safe space to safely vent my romantic frustrations and bleakness has mattered. Getting all of those stifling, humiliating, and one sided disasters of my memories about women out of my mind and into text, where others can see it, has had some impact.

The absence of pain is not pleasure. But it’s still the absence of pain. With my sense of humor and experiences from work I can handle the rest. This party, while short, was an interesting experience for me and my reactions. If this is the development of Zen, of no longer giving a damn about being alone anymore, then I welcome it. I’ve yearned to be free of these urges. Perhaps now that I have vented in essays for two years, I am closer to that state. Perhaps this is a sign that I have entered the last stage of mourning of my love life — acceptance.

And with my birthday coming up soon, that may be the greatest gift of all.

Dateless-Man vs. 2016

“I know, look at me, I’m hideous! Do you think I want to be this way? A freak!?” – Arlen Crane, “Guyver 2: Dark Hero”

Just like that, another year has come and gone. 2016 in particular will be one which may live in infamy for many of us. Many talented musicians, actors, and other celebrities departed this year, as well as the craziest Presidential election in ages. For me personally, it was a very strange year. I ended last year feeling that perhaps I would make a stand in my dating life this time. That something pivotal would happen, or could happen. That I was fighting a battle against time and it would be one of my last years to even attempt to reenter the dating world and garner any kind of success.

It seemed that even the desire to do so opened up the floodgates of fate. My job went through a drastic restructuring, and I had to focus on either readjusting or finding a new gig. I also suffered a knee injury which resulted in some recovery time for most of the summer. It wasn’t as bad as it could have been, and overall, I was lucky. The only reminder is a scar. I suppose if a woman ever asked, I could lie and say I got it in some bad ass manly incident. But maybe that’s thinking ahead of myself, as I am wont to do.

I began the year engaged in discussion with the ex of one of my best friends, trying to simultaneously bolster her own confidence and emotional needs while wondering when or if I could seek to ask her out. Opportunities don’t come up very often, do they? In the end she said she would take a break for her sanity…before getting in hot and heavy with some dapper dude she met. It didn’t help that she was looking for something permanent and long term, while I am the very definition of wanting to make up for lost time. It’s fair game to go after a woman who may want to settle down, but who hasn’t made such a thing bluntly known. It’s quite another to know that and pursue her for less than matrimony. At any rate, I ended the year debating whether I should take up my mother’s older horny friend on her painfully obvious desire to sleep with me in pursuit of her own fetish. I learned, or at least relearned, that my desire to lose my virginity is not an absolute zero sum game. I drew the line at wanting to sleep with someone I had no physical, emotional, or intellectual desire for simply because it was offered. I suppose it means I have integrity, but that and two bucks won’t get me on a bus.

I went over my flaws and my strengths this year, which was an interesting experiment.

In fact, this entire blog is an experiment. After another morose night around July 2014, I decided to get out some of my unresolved or repressed feelings and memories regarding my own lack of a love life. I’d tried to do so privately via a Word file that only I would read, but I never typed so much as a sentence. Somehow, the blog structure, under an anonymous name, with others reading it (whether a handful or dozens, or even hundreds) managed to get me to actually put fingers to keyboard. The addition of an audience, or at least a potential one, somehow got me to express some of these feelings in as honest a way as I could. My grandfather was a writer and lecturer; writing’s in my blood. Of course, he was also a bad ass merchant marine during WWII who literally run away to join the circus as a boy. It seems the more I learn about my family roots, the more I learn what a stiff I am. Everyone, even my mother to a degree, has had awesome adventures or exciting moments in their life. I’ve got nothing. I almost got run over a few times by cars as a youth, that’s pretty much it. Maybe if I had had that sort of life, even though my mother naturally raised me to not have to, I would have had the confidence needed to be attractive.

I’ve had a lot of time to reflect upon all of my past posted failures with women. And simply knowing that this is a “safe space” for me has helped. Any time I am really feeling depressed, or some incident has really gotten to me, I can type up a post here. Having that is a safety net which I didn’t have prior to 2014. It means a lot, especially all of the cool people who comment all the time. Usually this time of year is the peak of my depression, and this year hasn’t been so bad. Not that I am upbeat about the holidays or 2017, I simply haven’t felt as bad as I often do from October to March. Being consistently busy helped, but so has having this outlet.

I don’t do resolutions, and having some expectation or urgency to make a decision on my dating life last year didn’t help. If anything, the universe has spoken; just the mere inkling of wanting to dive into the world of dating again was followed up with economic uncertainly and a very physical and bloody injury. I am fighting a battle against time, where my years of vitality or ability to attract a lover who is potentially under 60 is growing more narrow. Now it comes down to whether I want to heed the universe’s warning or defy it. It would make it easier if I had any reasonable expectation for positive success, but I do not. I would have to act in the face of nothing but a history of failure, frustration, adversity, and misery, at a time when the stakes are far higher than they would have been in high school or college. I haven’t had it in me in the past, when I was younger and had less to lose. I don’t know if I have it in me now. I know it will be an emotional gauntlet which will drain some of my finite resources and spare time, with no reasonable expectation of success. I don’t know if I am game for that. My desire to not be alone would have to override my self preservation. Not being actively miserable isn’t the same as being happy or content, but it’s close enough for me.

I don’t welcome new years; I brace for them. In a few days 2016 will be no more, and a new year of potential horror, wonderment, or both will arrive. I’m sure some new adventures for me will arise for me to blog about, I just don’t know about them yet. Thanks for reading along with me for all this time, everyone! I hope to fill more posts for you full of my usual angst, opinions, and foibles with women next year. I would like very much to no longer be this way, to not have to be stuck with what seems are bad options or no options, or to be able to turn back the hands of time. But I can’t. The most I can do is move on, or onward.

Dateless-Man vs. Envy

And no, this was not an introduction to some Full Metal Alchemist fan art someone made. I just typed the title and that was the first thing I could think of.


I’ve said in the past that I have tried not to be jealous of my friends. It was something I definitely was during my teenage years which I have sought to purge from myself. But perhaps I have usually used the wrong word. Jealousy is feeling someone wants to take what you have. Envy is wanting what someone else has that you do not. It would be more accurate to say that as a teenager I was often envious of my friends. Most of them came from “comfortable” middle class households and had more comforts, and less worries and responsibilities, than I had. They also all had more social skills with women and had women show genuine interest in them. None of them turned 21 without having had sex and/or a few relationships under their belts. Pun intended.

I hardly even realized my own feelings of envy often propelled some of my often blunt wisecracks towards some of my pals as a teenager until I was in my 20’s and in college. I realized that was what I had felt, and that it was wrong to be so. It’s wrong to be envious of friends; I should be happy for them. As my friends, their joy and success is in a way, mine. So I took extra effort to purge myself of negative feelings towards them, to be happy for them when they did well as I should be. They’ve all gone on to be more successful and have much happier lives than I have, and I am genuinely glad for them. It can be a work in progress, but it is a work I feel I have gone a great way towards.

But occasionally I have set backs, at least with people who are more acquaintances than friends. One of the oddities of Facebook is that it allows you to befriend, follow, and chat with anyone, even people you hardly remember ever meeting. One of my online “pals” is a guy I’ll call “Skip”, who is at best a friend of a friend. I am sure I met him personally at some bar my friends took me to over the years once or twice at best. He certainly seems to have more fond or definite memories of meeting me. That’s always been one of the odd and frustrating things about my life. Men who I barely recall meeting seem to have fond connections about me and remember me forever. Women hardly know I exist. I easily make impressions on men without trying, but with women I may as well be a ghost. Such is life.

Skip is roughly my age (probably a little younger like most of my pals are), is a postal worker, is into many of the same geeky things, and keeps in shape. He’s coming off of a particularly nasty and sudden break up with either a wife or a fiance, which he has at times handled poorly. He projects a lot of stereotypical (at best) attitudes about women over it and clearly has some resentment issues. He’s been trying to move on and date again, but he misses that deep connection he once had. However, he has one tremendous advantage that he doesn’t seem to appreciate: women find him attractive. Skip sporadically shares stories online of when women give him compliments or flirt with him. This week, however, he “lamented” after a date about how “all these women want to do is hook up on the first date”.

To say that he was complaining about having too much water before a very thirsty man was an understatement.

I understood his plight – he wants a deep connection and some slow burn tension, not aimless hook ups – but I also stressed that being attractive to women was an advantage towards that goal that he could appreciate. But the more I typed, the more some of those hints of resentment and envy bubbled forth. It’s more complicated when you consider the secret that I have to keep close to my vest at all times – that I am a post-30 virgin. A few of my friends know, but he isn’t one, and none of the ones who do share it. I doubt many of them even think about it often, which I am glad about.

At one point I typed this:

I understand wanting a deeper connection with someone, especially after a rough break up. But at the same time, the fact that women are so into you at least physically at least means that your chances of finding it again are good, since you’re considered attractive. It’s a short cut towards finding some of those deeper connections. I mean, think of the alternative. Imagine knowing no woman would ever want to have you, even for a moment, in any sort of romantic way. I call times like that “being awake”. You at least know you can interest women, it’s just a matter of finding the right one for you. That’s a tremendous advantage. It may be frustrating when it’s not mutual, but at least take advantage of it to find someone who does bring that passion to your heart again.

As you can see I tried to use myself as an example of the opposite end of the spectrum. Skip continued and revealed the women he just went on a date with (or another recent one) revealed that she’d been involved in a threesome within the first 20 minutes of the date before complimenting his eyes. He enjoys “the chase” and wants more of an “old fashioned” woman such as Julie Andrews (seriously), although he did find it “flattering” that women found him so attractive that they always wanted to “hook up” with him. In addition to this, I did have another friend (who is a genuine pal, who I have known since high school) giving more of what I can call “typical guy advice”, such as, “Take the ass if it has been a while to perk up your mood. Hell maybe it’ll even develop into something afterwards” and “Well, assuming she enjoyed the threesome she awkwardly brought up there is always that avenue if you’re bored and feeling energetic”. This other pal is currently involved with his 5th or 6th lover, at least.

Next to me they may as well be discussing quantum physics from another universe. Their love lives and their reactions to women may as well be from another universe compared to me. I’m not saying that it’s wrong for Skip to dismiss being considered “a hottie” because the feelings aren’t mutual, nor is it wrong for my other pal to encourage him to “take the ass” if he can or is “bored”. I mean if the women Skip’s with are that into him, nobody’s being hurt. There’s nothing wrong with casual sex or short lived romances. As my pal said, many times something deeper starts off there; people “hook up” and then later decide they have fun and get along out of bed too. That’s perfectly legitimate. And as I said, I know Skip has been through a rough bit and could use some happiness.

It was just striking a nerve with me, I guess, to see him complaining about achieving what I have always dreamed of. It took all I had to not reveal my secret and say, “Look, you could be like me; a 30-something year old virgin who no woman who was too young to sign up for AARP has ever desired, so be grateful for what you have”. But that’s a secret I never want to reveal until I have to; least of all because of an earlier incident on Facebook several years ago where some of my friends who did know enjoyed a little “in joke” about it.

In the end I did admit:

I guess. Maybe I’m just too far on the polar opposite of it. [Skip] wants something deeper and passionate and he’s stuck getting a lot of vapid sexual attraction. I’m the walking anti-hormone, where all sexual desire goes to die.

I know that while some single guys like me lament about how “nobody likes us”, it can be especially frustrating to have people you don’t like “in that way” be into you. In fact I’d argue the only advantage to being one of the great untouched is that I have never been involved in breaking a woman’s heart. I can’t imagine putting someone through that. I always assumed if I dated, I would be the one who was dumped. I can handle and survive my own pain; I can’t control how others handle or survive their own. I know what it is like to have attraction towards someone who doesn’t like or acknowledge you in any way; I would hate to put someone else through that. I would feel so much guilt. Of course, dating women because you don’t want to “make them sad” or prolong a relationship you’ve already emotionally checked out of bring their own problems to them. Like many things in life, there’s no perfect solution; just choosing which flawed one works for you.

I’ve heard it said that’s never good to measure yourself by how you compare to others. Our own stories are unique, we’re told, and comparing our raw footage to someone else’s highlight reel will always result in heartache. I would contend that anyone who saw the highlight reel of my life and didn’t consider it underwhelming and pathetic is either delusional or starving in a third world country. But it’s difficult when it seems that every peer around you effortlessly achieves what for you is impossible. I literally cannot imagine a situation where a woman I am into desires me, and all around me I have peers like Skip who make that seem a forgone conclusion. When their love life has so many options for them that they can dismiss many of them.

I, on the other hand, am so desperate that there is literally nothing a woman could say which would repulse me from her so long as I was genuinely interested. I cannot dismiss any opportunity because I hardly get any. I spent the last couple of months seriously questioning whether I should sleep with a 60+ year old woman who is my mother’s friend who I am not into either physically or intellectually simply because I have no other options to ever lose my virginity short of a trip to Las Vegas. Desperation is the anti-sex equation, but what is the alternative for an older virgin? Because if I told someone, “I was just waiting for someone as special as you to come along,” that would be a bold faced lie, and I don’t believe in that. Unfortunately, “you’re the first one who thinks I’m hot for some reason I can’t fathom” may be honest, but it doesn’t inspire passion.

Perhaps my outlook would be different if my friends had been like me, struggling to understand and interact with women. But instead they’re all normal guys and I’m the freak. And it’s a role that I sometimes tire of. I tire of being the Xander of the group, the Orko, the Snarf. The funny sidekick who for one reason or another just is not on the same level as the others, and who is utterly useless in areas where it counts. I may be able to make cute anime references or occasionally spout some wise philosophy or insights into people, but I’ve not forged out a good career or figured out how to attract people I desire.

I wish I was so attractive to women that they gave me compliments or I had so many opportunities that I had to fend off the worst ones to get to the best. Instead I’ll probably be lucky to have one lover in my life, probably when I am far from my physical prime. I do hope that Skip finds what he is looking for and at least intellectually understand his dilemma. I’m not exactly looking for one nights stands either; I just wouldn’t refuse one if it arose with someone I liked. I don’t think I’d ever lament women wanting to sleep with me on the first date, even if they weren’t my type. I’d stop at “flattered”. Especially since I’ve never felt that in my love life, ever. I’ve always felt like an outsider, and when I interact with insiders, it really shows.

The struggle with envy is a never ending challenge. I hope to master it someday, but this week probably wasn’t it.

Dateless-Man vs. Best & Worst Dating Environments

I’ve explored a great deal about my love life, or lack thereof, over the past two plus years. If it was any colder, I could solve global warming single handedly. Theoretically, if I were to go about trying to change this, I would need to cater to my strengths. So I figured it might be interesting to examine my own feelings and past to sort out which areas I would be best or worst at. By “environments”, I mean a setting or location. It’s easier to list the ones where I do the poorest and then move my way up. Although since I am still one of the great untouched, one could say there’s no habitate or location where I do well or am genuinely considered desireable. I’m doing this in a free form, free association style so I don’t think I’ll be numbering any of them.

Dateless-Man’s Worst Dating Environments:

Bars & Clubs: I’m lumping these together because they’re similar. I don’t enjoy drinking to excess, and they usually have music that’s so loud that I have to yell all the time. But the biggest challenge is that not only is it hard to strike up conversations with random women who are strangers, but that it’s even harder to even find any who are alone. Even if you go to a haunt on “singles night”, most women will either be with a date (a man or another woman), or be with a gaggle of friends. It’s hard enough coming up with an ice breaker or opener, and having it be heard over the din of music and other people talking. But now I have to scope out who is single and who isn’t with a crowd. It’s incredibly difficult trying to engage with a group of people when you only want to speak to one. There’s no socially acceptable way to say, “Excuse me, ladies, but I only want to speak with her. May I have permission or is this unacceptable?” So you have to either wait until the group splits or try to engage them all, which is as many times as difficult as there are extra people there. And no group makes it easier. As soon as some dude comes over, the collective will judge him. And as soon as I might almost have the confidence or a good line, 5 other guys have already gone for it.

I’ve gone to bars many times with my friends since high school. I have always felt like an extra wheel, desperately piggy backing onto other people’s conversations. I never enjoy myself. The conversations rarely are about anything I have much experience with. Nobody is there to talk comics or anime, they’re talking jobs or lovers or so on. Adult stuff. There’s not much to say about work and even less to say about my love life. At best I am their shy awkward sidekick, making all of my pals look more charismatic by default. I do even worse at clubs, where the music is louder and everyone is jumping up and down. Even if there was any space to dance, I have utterly no ability. There’s no way to distinguish myself apart from “jumping moron #25” or “jumping moron #26”, especially if they’re in better shape and more at home in the environment. Since clubs have less space or volume for chatter, physical attraction is more important than even bars. And that’s always been one of my biggest hurdles, being unattractive. I don’t think I am ugly, but I’m hardly the sort who women tend to be immediately physically attracted to. At a club, this is the kiss of death.

I only went to a club one time without my friends (and even with them, I only went to about 2-3 clubs with them). I paid the cover and then tried to avoid being trampled. I maybe had one drink and stood around planning the best opener I could think of to a woman I had spotted at a distance who was totally alone. By the time I had, it had been about half an hour or more and another guy had swept in, and they were chatting at length. I was in my mid 20’s and it was quite a waste of time. At least when I am with my friends, I occasionally have someone to talk to and it is less embarrassing then being alone. But I’m not at home even with them in either. Bars and clubs really require you to overpower the scene with personality, looks, and/or charisma and I have none. It all feels so artificial. If you try talking to anyone, they know exactly what you’re after and will reject you before you get in a word. Assuming they even hear you.

Parties: They’re similar to bars and clubs. Most parties one is invited to tend to involve friends or associates. If they’re a regular crew, it can usually mean no one is single there. If it does involve some single women, then EVERY OTHER GUY will have the same objective as me. This immediately puts me in direct competition with other guys, whom I may already know, with direct witnesses. If you fail, you will be remembered for that FOREVER. It will be the story the group tells at every subsequent gathering until you all die. Even if you attended a subsequent party with a harem of Swiss bikinni models, someone will recount the one time you flamed out. If it’s a party where I barely know anyone, it’s similar to a bar or club, only with lower volume. You may have to interupt a group, which is awkward. Anyone you try to chat with knows exactly why you are there.

“Hi, my name is–”

“I am not into you, get away from me,  die in a fire please.”

“Hah, look at ____, she just told him to die in a fire! We’ll tell this story forever.”

Fuck parties. Ones that involve dancing are even worse. Thankfully I’ve never been to one like that. Just awkward social gatherings where everyone was coupled up aside for the one girl who was bulldozed by all the single guys, usually. Like Bars & Clubs, the downside to using icebreakers here is that they’re difficult enough to come up with, and always feel artificial. Everyone knows that a guy isn’t going to start up a conversation with a woman he doesn’t know (or barely knows) unless it is fodder for something romantic. That puts an air of artificiality on it, and a sense of futility for me as well.

And no, cosplay parties aren’t any easier. I went to one last year, actually. If you come to a party alone with no friends and can’t break the ice with women in groups dressed normally, nothing gets easier just because they’re dressed like Avengers or Sailor Scouts.

Speed-Dating: I’ve gone on four of these, including one last year at the New York Comic Con. I’ve typed at length about them, but clearly they are not a good environment for me. I have never gotten one full date out of them. They can be exhausting, and feel like mini job interviews. Even when  you feel there is chemistry, someone can have their fill of you quickly. If there are others nearby, they can hear your schtick ahead of time. Many times, the hosts’ attempts at comedy or keeping the mood light are as embarassing as the MC at a 4th grade prom. They’re a good way to meet dozens of women very quickly, and also a good way to be rejected by dozens of women in a hurry. The last one I went on I was genuinely proud of my performance, but it didn’t get me anywhere. Apparently, after a sample of the Dateless, nobody wanted another helping.

Random Street Cold Approaches: Basically, just chatting up women on the street or when circumstance happens outside. Admittedly, this is supposedly the hardest thing to do, a challenge to all but the most suave or sleazy of pick-up artists. Opportunities such as this don’t come up often, but when they do, I botch them. I’ve also watched in awe as others seem able to wade into these sorts of opportunities around them. It’s difficult enough for me to come up with an icebreaker or “go all the way” and try to get a name and number at a venue where in theory it’s socially acceptable, like bars, clubs, or parties. On the street at random feels even harder.

Dateless-Man’s Best Dating Environments:

Schools/Classes: By virtue of my one date in high school. Two things are to my advantage here. One is proximity; women in the class get a dose of me a number of days every week. They get used to me, maybe even hear me speak. And that leads to the other thing, regularity. I am not the sort of person women are just attracted to. I’m nowhere near as dashing, interesting, or charming as other guys. My strength is waring on people like a set of old socks. Not in an aggressive way, but in an, “Eh, he’s harmless/sort of funny” sort of way. The only dilemma I used to face is that if I made a move and failed, the rest of the semester would be awkward, and likely lead to gossip. I’ve heard it said that “things are only awkward if you make them awkward” or “people take cues from you on how to react”. I think that’s baloney; platitudes that people say without ever thinking about them. Unless cues are read properly and both parties are single, an unwanted classroom solicitation can be awkward or lead to gossip regardless. Still, I preferred the time to plan a move (which I never made), and the repeat opportunities. And at the very least, you have something immediately in common to talk about.

Warm Associate Approaches: Unlike a “cold approach”, a “warm” approach means you actually know the person. This may be a coworker, a classmate, a friend, an associate, or someone in your social circle. I can’t say I ever feel at home or comfortable in any setting involving women, but I feel less uneasiness with someone I am familiar with. It makes it easier to get an idea on their interests and a better notion of whether we click. This isn’t to say that I’ve ever succeeded here, either.

Online Dating: By virtue of my one date from OkCupid. In theory I have more control of my initial presentation. I can type and edit a profile, and try to pick photos where I look less horrible. You have more time to reply to any texts and can theoretically reach out to dozens of women in a very short period of time. Were I to try dating again, it would be exclusively through this medium. I really have no better options. I am not going to waste money on bars and clubs where all I would do is pay money to drink overpriced alcohol, stand around, and leave dejected. I can write well enough and if I zealously attacked this I could probably get at least one or two more dates eventually. Probably maybe almost!

Last Man On Earth: With all competition eliminated and all hope of future procreation available only through me…the rate of artificial insemination and homosexuality among women would rise about 1,000,000,000,000 %. However, by sheer virtue of being the only remaining option available, I would become more desirable and my rate of success would increase. Yes, I am taking this premise seriously.

Alternate Planet and/or Universe: Maybe I’m not. In theory in an alternate universe or planet by some sheer fluke of their solar radiation, atmosphere or gravitation forces I could be bestowed with powers far beyond mortal men there. It could be a realm of empathic psychics who find my awkward yearning and self loathing vulnerability attractive, in the same way that Cyclops is somehow attractive to Jean Grey, Psylocke, and Emma Frost. If a guy with a foreign accent can be considered “sexy” just by virtue of that alone, imagine being a guy from another universe. Maybe it’s a dimension where the stink of failure is an aphrodisiac. Or it could be a planet where all the males are gone. Look, I just don’t do well with competition.

Conclusion: It looks like short of getting lucky with warm approaches, it’s online dating or bust for me. It gives me more time to build rapport or set up something, or rely on my writing skills. It does take a lot of work and planning in terms of dates. And I do face having to overcome my virginity, my litany of faults, and my potential kinkiness. But with all other venues being far more difficult, it’s my least worst option. I wish I had a better one. I suppose a long term approach would be expanding my social circle, going to MeetUps and hoping either someone there is single or knows someone who knows someone who is single, but that’s far more long term than online dating. Besides, MeetUps which are geek orientated already have the problem of the one or two token women likely fending off more offers than they want. My ideal environment would be someplace where I had no memory of my endless failures with women, where I felt truly confident and accepted, and where I could sense genuine potential desire in the women around me. Short of a flight to Vegas, however, I don’t think any such place exists in this universe for me. I remain…the Dateless Man.

The Awkward Escape Clause Got More Awkward

No, don’t worry, I didn’t sleep with anyone yet still.

But there was a totally unexpected development related to my last posting here, “Dateless Man vs. An Awkward Escape Clause”. To recap, I went over how one of my mother’s friends and former co-workers, a woman in her 60’s named Dee, has harbored a crush on me for ages. I discussed how I feel no chemistry nor any sort of attraction to her physically or mentally (as in, personality). Considering my woeful romantic history and lingering virginity, I theorized that should I ever want to just “get it over with” without shelling out for a trip to either a sexual surrogate clinic or Las Vegas, Dee may have been it. However, a lot of this had been theoretical, me going from events which had happened years prior and picking a topic to write about.

A part of me wondered if I had misunderstood things. Or if I hadn’t, that it had been about 6 or so years since I’d seen Dee and things could have changed. Not that I had changed my own “squick” opinion about the entire affair. But I wondered if more of it had been in my head than reality. It’s typical of men to overestimate women’s sexual desire in them, even unwanted desire. I’ve usually never been like that at all. Usually quite the reverse; I usually assume I’m the lowest ranking man ever on the scale of “fuckability”. Or at least somewhere below Alf but above Hitler’s Literal Corpse.

Well, as “fortune” would have it, Dee ended up calling the apartment that I share with my mother (for economic and health related issues; she’s handicapped). I managed to reach the phone first. And while my conversation with Dee was brief, she left no doubt about her desiring me. In fact if she’d been any blunter about flirting with me, she’d have started quoting lines from porn.

One of the first things she said was, “I forgot how old you sound now,” in an impressed sort of tone. It made me remember that since she was Mom’s co-worker in the 90’s, she first met me as a kid. It further creeped me out a little that she had a crush on me now (and yes, I would feel the same if it was a man lusting after a woman he’d known as a kid, like Dorian Grey). She asked if I was seeing anyone, and mentioned a present she gave me when we’d had dinner (with mom) around the time of one of my birthdays. She’d gotten me a cheap ring (likely a hand me down) that I never wore. Dee said, “Well, you have my ring so I’m yours first,” before later adding, “Make sure to invite me to your wedding so I can cry in the first aisle” or words to that effect.

To say I was shocked was an understatement. My own replies were blunt as I waited for Mom to get on the line. Two or three words max, usually in disbelief. It was very awkward for me, and I could feel my anxiety rise by the moment. Now, as I mentioned in the last post, Dee has always been what some would say is a “liberated” woman. She is merrily promiscuous and prefers younger (white) men. I don’t look down on that out of purity or anything. If I met a woman who I liked who was similar (and I have), that wouldn’t effect my respect for her in the slightest. It just felt very awkward for a woman who I wasn’t into who was as old as my mother being so blunt about crushing on me. Dee has a weird sense of humor and is hardly shy about romantic subjects, so it wasn’t anything deliberate. It was just her nature. That didn’t minimize that brief conversation making me feel odd.

Afterwards, I told mom about it. She wasn’t surprised, but then again I imagine they’ve talked a lot about men over their two decade or so friendship. She knows about Dee’s crush on me and my own lack of interest.

So, let’s sum it up. For the first time in my life, I had a woman talk dirty to me over the phone (or at least come close). I was not only in my 30’s, but it’s a woman almost twice my age who I’m not into in any way, but is a family friend so I am obligated to see more than a stranger. Whenever I have dealt with anyone younger and/or someone I actually am interested in, I always have to read tea leaves or be put in a situation where revealing any desire will come with some measure of pain for somebody. But when it comes to old ladies in nursing homes or friends of relatives, by god they think I am sex on a cracker. And people wonder why I am so romantically frustrated and find this avenue so hopeless. It would be a hilarious comedy if I wasn’t the one living it.

When 2016 started, I thought it might be a pivotal year in terms of my romantic strategies or lack thereof. Maybe I was, once again, looking for a sign of whether any redoubled efforts would be rewarded. Ever since January, I’ve had a lady friend come to me for advice online and to buck up her own esteem from love lost, who later went on blossom after my help to her. I am genuinely happy for her, just disliked being put in a situation where it was either risk upsetting an emotionally fragile woman who just wanted someone to vent to sometimes, or be alone forever again. And then I fell and hurt my knee at the start of the summer, and needed months to recover. Now this. I have the choice for obvious and easy sex with an old woman I don’t desire in any way but clearly has the hots for me, or wait another few months and be an even older male virgin. Aren’t choices fun? Especially whenever it’s always choosing one in which you lose the least?

I got my sign. The universe has spoken. My love life is a miserable, frustrating, underwhelming joke with no good options or prospects. If I were to proceed anyway with any attempt, it would have to fly in the face of every blunt sign that reality is telling me. There is not one reason why I should feel confident in having any better success than when I was younger and could rely more on youth and proximity. This incident was just another straw in my Underwhelming Haystack of Love. The Magic 8-Ball has once again told me, “ALL SIGNS POINT TO NO”.

I’m not saying I’m giving up, even though I probably functionally have for a long time. I’m more experienced now, and I think I talk to strangers better due to the job I’ve had for years. I know at least intellectually that I’m not the absolute worst out there. I have had many people buck me up online on this blog, which is appreciated. But I realize now that in doing so, I would have to be prepared to act against all logic. In this, trying to actually make a love life happen, I would have to hammer a square peg into a round hole. I would have to reject every single sign the universe has sent me and go, “I think I can anyway”. I either have to have the determination of a super-soldier or the stubborn delusion of a hopeless romantic masochist. I don’t know if I have either in me.

I have no intention of taking up Dee on her “offer”. I’m just not into her in any way. I am not so desperate to lose my virginity that I am willing to try to sleep with an old woman who has a fetish for me who I am not interested in either physically or intellectually. That’s either a sign of integrity or a sign I simply don’t want to lose my virginity as badly as some others. Either way it means the same thing. Bars don’t hold “wet integrity contests”, after all. But as we near the later end of the year, with another birthday on the horizon for me, I have to look at my options and status honestly. I am woefully behind schedule in terms of romantic experience. I will have to work 50 times as hard to get half as much as the average person got when they were 15. I do not have youth or proximity on my side. I have no distinct advantage when compared to almost any other man. Apparently only old ladies think I am worth touching. A shame I have no desire to be a nursing home gigolo.

These are really the only options I’ll ever have. Whatever is in me is really all I will ever have to work with. I’ll have to be prepared to work against the grain of every instinct I have, every sign the world around me has shown me, and without any positive reinforcement. And all that just to, what, get a second date? In a more competitive market, with so many disadvantages? There’s an element of luck and chance in these affairs, and I’ve never had it. I’ve followed the “just pursue your passions and someone will come along” advice for much of my life, and clearly that has never happened.

There is more to life than relationships. There are more things I can do besides find a lover. There are more things to enjoy than sexual relations. It may have been a brief and very awkward telephone conversation, but it certainly has sparked a lot of thought. Thanks for reading, everyone!


Dateless-Man vs. An Awkward Escape Clause

“Beggars can’t be choosers.” – Proverb

Being a man who is severely inexperienced with romance past a certain age brings with it a lot of interesting dynamics. By interesting, of course, I mean either awkward or terrifying. You have things to keep secret, yet which can’t remain secret should you proceed to resolve them. You have less perspective on this very common fact of life, and find yourself having to dance around conversations or expectations to avoid giving it away. And you also have to combat certain attitudes about sex, love, and dating not only from peers, but society and your own head.

There tend to be two major schools of thought regarding older male virginity. One is to gradually become more fulfilled with your own interests and at least try to make any lovers you have meaningful. After all, a very common complaint about more “experienced” people is some regret that their first time wasn’t with someone they would have liked, or they had a few regrettable sexual encounters for dumb reasons. Men especially are encouraged to treat sex like experience points in an RPG, or think of it like that. A lot of anxiety I and others in my lot feel is the sense that we are not “real men” unless we can assert it through either sex or violence. This is baloney based on sexism, but it persists. Even in circles involving less experienced men talking about their fates or thinking about it themselves.

One attitude which can persist in some places is the sense that an older male virgin simply has unrealistic standards. That all he (universal he) wants is a perfect living doll regardless of his own physical state and anyone less is ignored. That if only he was more willing to “take what he could get”, he’d “get laid” and so on. And there is some truth in this for some; some people do have unrealistic standards. I never thought I did; the sheer volume of women I have found attractive as I went about my daily routine for over 30 years has been too varied to suggest that. But to me it represents a paradox. Desperation is seen as an unattractive trait; yet any older male virgin who isn’t so desperate as to leap upon any and every sexual opportunity, no matter how vile or awkward, “just doesn’t want it bad enough”. Even peers who share this state can occasionally be just as judgmental in this regard than any studly jock.

Which brings me to the subject of this article. Anyone who’s been reading along with the blog for a while may realize I sometimes use lengthy introductions to avoid having to discuss subjects I find awkward. And I may as well type it out before I clarify. The gist of is that my mother has a slightly older friend of hers who has usually made no bones about finding me attractive, and I could probably lose my virginity to her without much effort on my part – if only I was willing to sleep with a woman I don’t feel anything for who is friends with my mother.

An “awkward escape clause” indeed!

I briefly mentioned my mom’s friend before, in “The Last Actual Date”. She was the one who set me up on it (with a much younger co-worker of hers). A lot of backstory is needed. For a long stretch of time, my mother (before she was disabled) worked at an artist’s school and met a lot of wild and wonderful characters there. One of them is a woman I’ll dub “Dee”. They’ve been friends maybe twenty years or more. And like a lot of older women who have been friends over a decade, they have had periods of time where they didn’t talk and hated each other, only to reconcile eventually. Dee is roughly around my mother’s age (call it early 60’s), works as an artist’s model at the school, and is both a little eccentric and very “liberated” in her romantic life. She is also a major fan of Superman. As far as I know she’s never been married nor doesn’t seem to want to marry. Much like my mother did in her youth, her own sexual conquests almost seem to be a hobby. “I like sleeping with young white men,” is something Dee’s said in my presence during dinner. Her current on again/off again boyfriend is a priest who is cheating on his vows with her. She’s also hardly monogamous and, like mom, can sometimes be a bit “risque” when talking about sex. I’ve met her at various times throughout my youth and once I was in college it seemed to get out somehow that she found me attractive.

The last time I saw her was maybe 7 years ago when she, my mother, and I had dinner. It was around either my birthday or Christmas and she gave me a cheap hand-me-down ring as a gift. It was maybe a couple of years after she’d set me up on that blind date with her colleague (which Dee apologized for, which she didn’t have to do). I didn’t talk too much but Dee and mom talked plenty. At the end of the dinner mom seemed to reaffirm the rumor that she “liked me”. I hadn’t noticed; Dee seemed to talk about her usual topics. Her torrid dating life, some of her thoughts on society, happenings about her job, and Superman. At one point I joked about her “having a shrine” to Superman at home and she deadpanned, “How did you know?”

The biggest problem with such a situation with Dee is that I have no genuine feelings for her. We don’t seem to click or have any chemistry in terms of personality. Without describing her looks the best way to put it is that she doesn’t click for me physically. She isn’t ugly but I just feel nothing there. It seems beyond obvious that Dee wouldn’t mind a “booty call” from me, or at least once did. However, I obviously have never taken her up on that or explored it. Least of all because I find it awkward that someone who is my mom’s friend and around her age is into me for a “booty call”.

One of the oddities of being among the romantically inexperienced elder male communities (whether I want to be or not) is that sometimes they (or we) have a knack for being victims of “traditional male culture” while also strictly enforcing it. And I say this with personal experience in how I view myself. After all, a great deal of why I have a poor self image is because I am unable to fit my own criteria for masculinity which is within my own head. The anxiety older male virgins feel is not just coming from society and culture norms, but from their own feelings and enforcement of it. And one of these dynamics is the sense that “a real man” takes any sex he can get (so long as it is among consenting adults, although too many men see that as debatable). If he doesn’t, so goes the theory, then he “doesn’t want it enough” and “deserves” to be a virgin and unloved. Traditional “male theory” is that it shouldn’t matter that I feel no desire emotionally, intellectually, or physically for Dee, nor should any feelings regarding her age or role in my mother’s life exist. I should just capitalize on the opportunity, especially as someone who laments at length about being a virgin. Especially as someone who at least entertained the notion of prostitutes in Vegas or sexual surrogates inside my own mind as a temptation. I could easily imagine at least one of my friends (probably a guy one) encouraging me to put all this aside and try to move forward with this “opportunity”.

One of the many frustrating ironies about my life is that while I haven’t ever been considered attractive to women around my own age who I was into, much older women have always found me attractive. During the last few years of my grandmother’s life I spent a lot of time in various nursing homes and I can’t count how many old ladies blatantly flirted with me. Nothing like poor vision, heavy medication, borderline incarceration and at least a half century (or more) of an age gap to make me a stud, huh? Every man wants to be a “lady-killer”, but with that crowd it could get too literal. Maybe there was a time where men like me were considered attractive, but that time is long past and isn’t coming back. I try not to get nostalgic for an era I never lived through. So add this factor into the situation with Dee and one can see how it can seem complicated when I think about it.

Plus, how would I even go about it? Just call her up and ask her out? Have a ridiculously awkward “date” before the…other stuff? And attempt to go through the physical motions with someone I all but literally have no feelings for? Would grinding through the physical act of sex with a willing person even if it went against what I am comfortable with be better off for me in the long run? Besides, I’ve never talked with Dee bluntly about this sort of thing to begin with. In theory, one of the few “advantageous” (or “less horrible”) parts of being an older male virgin is supposedly getting to have some more choice about one’s “first time”. In real terms, too many people out there were raped or molested or pressured into sex when they weren’t ready, and it is a source of trauma. In other terms, many people tend to regret their first time, usually with someone in their youth who they slept with due to the same reasons why I even fret over this thing with Dee – social pressure and hormones. I’m older and not enslaved to my hormones, and old enough to know better. This doesn’t even get into some ramifications of those around me. While I am sure Dee won’t “attach” to me or see it as anything deep, how would my mother react? She’s an ex-free love hippie herself (a fact which makes my virginity very ironic) who has said she would understand if I did so, but she’s also said that knowing my position of having no intention of doing so. Lord knows it could drive a wedge between mom and one of her longtime friends. I am not a prude and have no issue with a “booty call” or a promiscuous woman (so long as all parties in her life know and accept it), but something seems off about a situation where I have no emotional or physical desire, and all it would be is a physical transaction I feel I am doing for “my own good”. Literally all I would get out of it is finally being able to not be a virgin anymore. A sexual surrogate is part of genuine sexual therapy, and in theory a Vegas prostitute would be someone I could choose specifically because there would at least be physical desire there. And those are options I have rejected outright.

Is it wrong to want to have a first sexual encounter where I at least have some genuine feelings for someone else on an intellectual and/or physical basis? Even for just a short period of time? I don’t mind being the object of someone else’s fantasy or booty call, it just feels off to just go into it for the act itself, and for there to be no kind of passion or genuine energy in it. But perhaps I am wrong. Perhaps I should jump at this chance to finally shed my shame in a perfectly legal and consenting way. Most people’s first time is hardly perfect and mine likely won’t be either (especially since I am sure I will be physically underwhelming for the woman and she will either be disappointed or disgusted). But something about it feels off, feels wrong.

Deep in my heart maybe I know that the sheer act of sex won’t “fix” or alone improve upon many of my faults and problems. And if it won’t, maybe it isn’t worth it to lose it in a deeply uncomfortable situation just because it maybe presents itself. Unfortunately, the alternative is more lonely nights, more feelings of woeful inadequacy, and more lost months and years in a pit of despair over this. You can’t put a value on integrity, but it won’t keep you warm at night either. I am tired of being a freak, a comedian’s punchline, a facade of a man. Yet I am apparently not so tired of it that I am willing to take advantage of an old woman’s fetish with a wince just to check a box off a list. It is who I am. And that is…the Dateless-Man.