Dateless-Man vs. General Virginity Opinions

It seems that when you’re  what is termed an “older male virgin” (that is, an American man who hasn’t had sex by age 21 or so, or in my case, by age 30-plus), not only are you up against a variety of factors (such as time and inexperience), you’re up against general social norms. Greater society (men in power) seeks to classify everyone and sets up rigid rules which everyone is supposed to follow or embody or live up to. Those who don’t tend to be seen as deviants at worst and at best “a bit off”. Even if you follow as many of those “rules” as you can, sticking out in even one or two elements can place you in an area apart from others where you’re on the outside looking in. And often when those of us who have the secret of being “older male virgins” express feelings such as anxiety, fear, and even frustration about our state, it is common for those responding to claim that it’s not as insurmountable a status as we think. “Nobody has to know unless you tell them,” is one platitude I’ve heard; another is, “It’s all in your head.” And as one thinks about things rationally, these platitudes (or to be fair, perspectives) can sound sensible.

But sometimes you encounter an example within everyday life where someone you know, by complete accident and in a completely impersonal way, reminds you that these social norms do exist. That being one of that “community” of older male virgins does place you in a position of difficulty or lowered status compared to most other men out there. And that perceptions about you, should you reveal your secret, face greater odds of being negative.

(For the record, I haven’t typed a post directly related to my angst about my virginity since the start of August, so I’m about due.)

This anecdote takes place earlier this week at work. I’ve been hesitant to reveal exactly what I do for a living but I will say that it involves a lot of talking on the phone. So much so that I imagine if I did reveal it all, someone would reply, “My god, you can do all that and you can’t talk to a woman!?” To which my reply would be, “Give me a set script, a list of rigid rules of engagement and no other avenue but my voice and then get back to me.” At any rate, it was a full night shift towards the end of the week and as usual, my supervisor was trying to keep the morale of the office high and the energy positive, without distracting anyone from working hard. And as my line of work usually attracts various types of “characters” to the office, he was engaged in some banter with one of the top men in our department (who I’ll dub “Ned”). Ned is an ex-con in his 40’s with plenty of experience, and an ego which far surpasses it. Yet that ego and confidence are part of why he does well, and trash talk is a part of his demeanor. Since my office employs mostly men (and most of them under the age of 25), such things are common. Ned and my supervisor go way back, and while they trade a lot of barbs against each other, it’s always in jest and never personal.

At one point in their never ending game to out-diss each other, my supervisor was responding to one of Ned’s many statements of self congratulation and arrogance around the office with, “Please don’t be a 40 year old virgin like Ned is! Please, please, PLEASE do not be a 40 year old virgin guys! Take care of that!”

Naturally, the joke was that Ned is far from a virgin. He has a daughter with a woman he’s not married to, and even in the time he’s returned to the company over the past 3-4 months he’s seemed to go through at least two lovers (and briefly lived with one). And naturally, “The 40 Year Old Virgin” is a famous Steve Carell movie from 2005 which has become part of pop culture. I’ve heard good things about it, but I never watched it in part because I feared it would hit too close to home and upset me. But naturally, my supervisor giving that line (and the thunderous laughter it got from the entire rest of the office) showcased that sentiment about older male virgins. It is that they’re lame, defective, bottom of the pecking order, lower than other men, and less desired by women.

What did I do? I faked a smile, but I didn’t laugh. I didn’t feel personally insulted, as I haven’t revealed my secret to anyone in the office and the line wasn’t directed at me. I’m sensitive, but not that sensitive. My supervisor and I get along very well, even if like most people he likes to joke around a little. Once several years ago he played a minor prank on me in which he tried to convince me that one of our co-workers who was a woman liked me (and in which she was a willing accomplice). I initially smelled a prank and refused to believe it, even with the two of them trying to convince me that it was true. It was only by about the fourth round of, “No, seriously, she likes you” did I appear to almost swallow it and allow them to get to the gist of the joke (she made sure to tell me she had a boyfriend, and that it wasn’t her idea). I can take a joke and I had no hard feelings about it, even if I hardly laughed (and, ironically, I did have some crush on her). But that was years ago, and that co-worker had long since left the company. My supervisor, and no one in the room, could have any idea of how close to the mark a line like that was for me.

Which is the point. Being a post-30 virgin is so rare that it does seem like the stuff of improbable comedy cinema. And while this was an office full of men, the opinions of most women on the subject aren’t a whole lot more flattering. There are far worse secrets to have to keep to one’s vest, but this situation only reminded me that my “scarlet V” is really the “secret shame” that I sometimes term it, and it is genuinely something I have some merit to fret about.


Dateless-Man vs. New Year Doldrums

Just like that, an old year is over and a new year has begun. And just like that, I went a month without a post. I genuinely try not to do that – as ideally I like to get in roughly two posts a month – but sometimes it’s unavoidable. Now that I have gone through my mental vault of previous memories and failures with women, and considering I have waxed on about many related topics more than once – especially my own virginity – there sometimes isn’t much use in typing up a blog entry which is essentially “same ol’, same ol'”. But now that it’s at least February I at least have enough to grouse about for a few thousand words.

As stated some time ago, I consider the period from October to March to be the half of the year where I am usually at my most morose and/or depressed. The change of season from fall to winter can do that to plenty of people for a variety of reasons, such as less sunshine. For me it usually is because from Halloween to Christmas, New Year’s, Valentine’s Day and ultimately my own birthday, I am faced with a multitude of “special days” which only remind me of my own loneliness and the seeming futility of my own state in that regard. I can honestly report that since beginning this blog in summer 2014, in the name of aiding in my own mental health via expression, I’ve felt less of these negative feelings this year than last. I do believe that having vented a lot about my own past and foibles with women, as well as simply knowing I do have a “safe space” to type about my own  frustrations where I won’t have to fear anyone I “know” finding out about it is helpful. This isn’t to suggest that I’ve suddenly become a joyful optimist singin’ in the rain, but that at worst, having this blog (and those who read it and contribute to it) has at worst done no harm and at best given me an extra cushion to my own frustrations or thoughts.

But that’s not the only thing you’re hoping to read, is it? You want some updates into my adventures (or lack thereof)!

There has been a development involving a recent online situation I had with a woman I dubbed “Carrie” in “The More Things Change” back in November. It involved me becoming online friends with an acquaintance who I also realized was a friend’s ex who I naturally developed a crush on (and just as naturally, saw no viable way to reveal this without pooching things). As the months wore on, Carrie would continue to chat with me via Facebook, albeit mostly to vent to someone about her own woes with relationships and dating. I usually did my best to comfort her and offer her advice, which she seemed to appreciate (even if I did note the irony of it coming from me of all people without revealing my own secret). She’s commented how I “make everything seem so reasonable” and “give the best advice” more than once.

As we continued to chat, and I continued to weigh my options, she finally told me of an episode where she was considering revealing her feelings to a longtime friend who she believes likes her, but never made a move until one drunken “sort of” kiss. She stressed how she usually likes to keep “friends” and “lovers” as apart as possible most of the time, which was why this was bugging her out (in addition to her own esteem being shot by a few rejections). As someone who adores her I of course can’t imagine why any man would reject her but naturally I keep this to my vest (while bucking her up with compliments). Once Carrie got into how out of wack it is for her to consider dating a friend, especially one who wasn’t me, I realized that any sort of revelation of my own would likely do little more than complicate matters. It was something I feared back in November but as the new year happened, became more of a sure fact. According to her Facebook updates, Carrie is now dating someone – whether it is that friend or another dude, I have no clue – and appears far more upbeat than she was at the end of the year. I’m genuinely happy for her. While it certainly would have been nice for her to have “chosen” me or been more receptive to that potential, in the end we are going in two different directions. She is over 30 and looking to settle into something more long term, and I am even further over 30 and have barely even begun to have a love life. In all honesty she deserves far better than an inexperienced man-child virgin with a crappier job like I am, and I know it. I am stuck in this void in which I hardly want to settle down, but I’m not entirely eager for one night stands either – as if I could get either. Still, that’s not the direction Carrie is headed. I’m mildly disappointed but overall not surprised. My romantic life has never been that easy or clear cut before, why would it be so now?

Relating to my most previous installment, I am still planning out the best “imperfect strategy”. To this end I have begun reading some advice columns here and there across the internet. Two of them can also serve as the best examples of what is often out there for men in my situation (outside of standard “pick up artist” sleaze). There is Doctor Nerdlove, a former PUA artist who encourages a lot of progressive ideas with both his articles and the community of people he fosters in his forums. Another is “Good Looking Loser“, which essentially tells you that all you need to do is work out and keep plugging at online dating until something gives. The former is a very welcoming place and many of the people there give good ideas and advice, even if it sometimes can be almost too understanding. If you don’t think you have what it takes to slog through it (like me), everyone is cool with just chilling until you’re 100. The latter, of course, will scream at anyone to just hit the gym and hit up enough women, or you’re a weenie. As always I feel caught in a crossroads.

My least worst option is giving OkCupid a genuine try. I decided (or rather, was convinced) not to hand over money to the website to see my “likes” because many of them could be outdated; merely a total since I first joined in 2006. The best idea is to restart from the ground up with a new profile. Research shows that keeping it short is usually for the best – no more than about 97 words a section. Ideally having at least one profile shot which is taken professionally (as in, by a paid and/or trained photographer) is best, with selfies-via-mirrors to be avoided. But most of all, it requires a slog. Ideally, only 1:20 or 1:30 or 1:50 (etc.) will respond, and out of those maybe 1:20 or 1:500 will agree to a date, and out of that maybe 1:20 or so on will want another. Online dating is perhaps the best and easiest way to make one last gasp at making up for lost time, but it can also be just as frustrating and daunting. I didn’t have it in me when I was in college in my 20’s, or even in my late 20’s when I began my latest job. Now that I am facing down another year, getting another year past 30, being another year of old baggage, I genuinely don’t think I have what it takes to go through with it, to grind it out like I have to (especially without messaging people I genuinely have zero interest or compatibility with just to make up numbers). I am sure I can avoid coming off like a creep in those “private messages”, but I doubt I will come off beyond mediocre either. Yet I am not getting any younger, and as hard as it is now, it won’t be any easier when I am over 40, or over 50. This really, really, really, REALLY is it. I either make a shot sometime soon or I may as well never bother, ever, anywhere. And I am not sure what I want, or what I have the fortitude for, and whether I have any attributes which would help me for either.

So, 2016 begins much like 2015 ended. At least so far.


Dateless-Man vs. Speed Dating II: The Wrath of Comic-Con!

Despite that title, I’m not actually a Trekkie. Just related to one.

At any rate, before Halloween creeps up on us and fall begins, it’s time to blog about an event I’ve promised since the start of September. After a six year lapse in doing anything involving dating besides monthly (or bi-monthly) checks ups on my neglected OkCupid profile, I finally decided to do something a bit impulsive. I agreed to go to a speed dating event which was held during this year’s “New York Comic Con” roughly three weeks ago. While speed dating may not be the most ideal setting for shy, anxious people, it’s an activity I have some experience with – I went to three speed dating shindigs back in 2009. This event was held by a different company and naturally at a different venue. Rather than a bar in Manhattan attracting plenty of “normal” people, it was held at the biggest comic convention on the east coast where everyone was assured to be some type of geek. I’ve never had any success at speed dating (or slow dating, or any dating, ever), but I regretted not trying it out at previous cons and I figured some of the odds were in my favor in terms of shared interests.

Things are different than they were six years ago. The success of comic book movies and TV shows have made comics more mainstream than they were back then. I also have had four years experience at a job which literally forces me to talk to over 200 people a day, every day, five days a week. My grandmother’s since died and I’ve gone through four years of turmoil and struggle with my sick mother, our slum of an apartment, and other struggles. I have insisted for many installments that trying to date again after being years behind the curve is useless because I’m the same person fundamentally as I was in high school, college or in my late 20’s. At the core this is true, and many of my insecurities remain. But at this event I did notice that some things had changed within myself, at least for an hour or two.

The event was organized by “NY Minute Dating” (NYMD), which offers parties and events for little more than $25 elsewhere. They held speed dating events on all three days of the con, but I chose to go on Friday, October 9th, with the theory that if I hit it off with anyone, we could hang out at the con the second day (or at the very least, I didn’t have to get up early for work the next day). I registered in advance and arrived a little less than half an hour early. While plenty of people were in “cosplay”, I wasn’t. I was clad in my usual studded leather jacket, jeans, and a geeky t-shirt (in this case, centered around Ninja Turtles).

Some things were different between this speed dating event and the ones I went to in ’09, and others were the same. The similarity involved the women being stationary, seated at tables and assigned number cards; it is the men who visit each one for 3 minute intervals before “rotating” to the next one (at the sound of a bell). Everyone is given a sheet to jot down the first names of the people you chat with and like for matching purposes later. The biggest difference were the demographics. In the more mainstream set events from 2009, the women typical outnumbered the men; in fact, discounts were often granted to men to get them to sign up in greater numbers. At comic-con, it was the exact opposite. Between women who registered in advance (which was the preferred method) and ones who showed up on the spot, NYMD was barely able to fill a room with 30 women for longer than a couple of minutes. The male spots, however, filled up quick and there was a line of them waiting outside for any vacancies which stretched for several yards. I expected this, which was one of the reasons why I arrived early.

I was a bundle of nerves as we were preparing for the event, with all of the men lined up on one side of the room before everyone was assigned their first “positions” seated with the women. I chatted with some of the dudes alongside me about this and that. Having done speed dating before, I came off as experienced. However, despite this being a “geek” venue, there were a variety of different guys. One (who was cosplaying as some ninja type character) was quite athletic, energetic, and traditionally handsome. A younger one (cosplaying as Marty McFly) was a physics student, and we talked a little. Not long after I also shared some words with another fellow who fretted about “creeping out the girls” and had a bit of an overbite. Despite preferring women with similar interests, I was under no illusion that this would somehow make them more tolerant of certain things than women who weren’t into geeky things. The proof of this seemed to be at least 5-6 women flat out leaving the event before it started once they got a first glance at the line up of the men available. I once heard a saying about trying to date at a con; men have no chance, and women can take their pick. This left almost two dozen ladies left to have speed dates with. At least a third were cosplaying, and I managed to recognize most of the characters they were dressed as.

One of the first things I noticed was how young most of the crowd was. The sign up site said that the event was for people aged 21-35, but I noticed a grand total of one person who I thought was older than me (and barely more who were my age). Nobody checked ID’s at the door so it is very possible to have lied about age and gotten in without being 21. A gentleman doesn’t ask a lady’s age and it wasn’t a question which came up with every date, but it was very common for most of the people present to still be undergrads in college. At least half of the women I talked to couldn’t have been more than a day or two over 21. While I am willing to date younger women, they were a bit younger than I usually prefer, and at times the age gap seemed obvious. I used t-shirts and/or cosplay as an icebreaker topic and once I mentioned things such as being a fan of the original Ninja Turtles cartoon from 1987 – before some of these women were even born – I felt a little bit like Dorian Gray or Dracula (only without the charm or wealth). A slight majority of the women there were white, but there was also many women of color there as well; mostly of Asian or Middle Eastern heritage. Such things don’t matter to me; I’m not someone who avoids women of color nor has a fetish for them as some men may.

I started out a bit nervous, and it is possible the first lady I spoke with helped me fight through a lot of that. A Latina in her 20’s, she had dark hair and was not only very assertive and seemed to be proud of it, she also worked as a mortician as well as an avid kick-boxer. I got the feeling she may have killed me if we were on an actual date. Everyone else seemed far easier to talk to in comparison afterward, and I had roughly 21 speed dates in total – which makes it a perfect blackjack. I easily had the best conversations with two women who were likely friends because they were both cosplaying as gender bent versions of Blue Beetle & Booster Gold – a classic buddy team from DC Comics. It was mostly just 3 minutes of talking about comics and other nerdy subjects. I also had a fun conversation with a woman dressed as Frodo from “Lord of the Rings”. I must say that while there were only one or two out of that 21 who I could say I had no attraction to physically, there were others were there seemed to be little chemistry with, and that 3 minutes felt like an hour. The DJ who kept music flowing and rang the cheap cowbell to mark the time was trying to keep the atmosphere loose, even though he seemed to be trying too hard to be funny.

What surprised me about my own performance was the ease with which I seemed to talk. After initial nervousness, I was in a zone. Sure, I did have a bit of a canned opener and I did have to watch myself to avoid talking too much. But I would work with what I got, try to find common ground. I seemed to have more of a sense of when I thought things weren’t clicking with some women. I think I came off sounding far more confident and fun than I usually am, even if I also likely came off a bit old as well. I proved to be quite a chatterbox, even willing to poke fun at myself (when one attempt at my opener felt awkward, I owned it by saying, “Sorry, it’s just my icebreaker, let’s carry on” or words to that effect). Considering I was hardly the tallest or most handsome guy in the room, I honestly don’t think I could done any better, and I rarely feel like that about anything – especially things involving women. I took the best shot I had. Perhaps my day job caused me to rely somewhat on an opener which felt scripted, since that is what I am used to. It did help, as well as the fact that I was more in my element with fellow geeks talking more about hobbies than with more straight laced types. Still, most of the women there were talking about college and just graduating, which once again put the onus on age.

Once the event was over, one was supposed to log into the company’s website the next day and click on all the names of the people you liked. If they also liked you, emails would be exchanged. So out of 21 people, there were roughly 9 that I felt enough of a connection happened that I would be willing to go on a full date with. That’s almost half, which I think means that my taste is flexible. I mean, why would I want to continue contact with someone who I didn’t click with for even the 3 minutes? I’d rather not use anyone. Everyone had up to 5 days to send in their clicks and then allow the NYMD wizards to work their magic.

I wound up with exactly zero matches. Despite the hi tech change – previous speed dating events with another company would use physical sheets instead of website clicks – my result was the same as before. There are harder ways to be rejected by 9 women within two hours, but in the end it turned out like it always did. At least since 2009, I can technically claim to have been rejected by at least 40 women at these events. Nobody can say I never tried.

I’m of mixed feelings about this. During the event itself I was enough in a zone where I thought I could actually try real dating again, at least online, if I had more heart to give it a genuine, honest try. Speed dating is a bit of a shortcut and it’s a shortcut which doesn’t seem to be working. The question is whether I have it in me to give genuine dating a try again considering how far behind the ball I am. Not even women at comic con wanted more than 3 minutes with me. What chance do I have with women outside of my element? Why should I expect any different result now?

Happy Halloween, everyone! I am sure I will have another post or so in me in the future, I’m just not sure what it will be yet.

The “Back to the Future” day blues

Yesterday (if only by a few hours) was the day in which in 1989’s “Back to the Future II”, Dr. Emmett Brown and Marty McFly went into “the future” of approximately 30 years from their present time of 1985. As the classic film trilogy became more of a sensation and ultimately a nostalgic franchise, much attention has been brought to the date of October 21, 2015 and seeing where the film was right and wrong. Plenty of films, TV shows, comics, and books have glimpsed at the future and were right or wrong to varying degrees. Flying cars aren’t commonplace and the Chicago Cubs won’t be going to the World Series (much less winning it), and the “Jaws” franchise mercifully stopped well before the 19th installment. As part of Universal Studio’s push for promotions (and to sell a new blu-ray of the trilogy), there have been videos shot about the film, cast reunions, a new comic series, and a lot of media attention both online and off about it.

I enjoy the trilogy overall and normally am all about celebrations of geeky things I like. Yet today’s celebration of “Back to the Future” reminded me of my own reunion with the films several years ago. I got an unexpected feeling of depression and sadness from it around 2009-2010, and some of those feelings returned today. I suppose it was “triggering” for a brief period.

The sequels were great fun (even if “Back to the Future Part III” is usually considered the poorest of series) but those feelings arose when I re-watched the original 1985 installment those years ago. I won’t summarize the film, but the gist is that Marty McFly has to go back in time to when his parents were teenagers in the 1950’s and ensure their romance blossoms to keep himself from vanishing from the time-stream after an experiment with Dr. Brown’s famous Delorian goes wrong. The film has everything – drama, comedy, big ideas and a lot of imagination, and music. Yet in “fixing” the past, not only does Marty ensure his own birth, he also alters history enough that his father George McFly goes from being a simpering weakling who is stepped on all the time towards being far more confident (in particular, by socking his lifelong bully, Biff Tannen). It changes his entire life and the entire dynamic of Marty’s family. In addition, Huey Lewis’ “Power of Love” song is a key theme of the film, and naturally Marty himself is “Mr. Cool” of the mid 1980’s, with a girlfriend, a skateboard, and a fun, aloof demeanor. He goes through development to overcome his recklessness in the sequels.

At the time, I was not only still a lonely, single virgin, but I was also unemployed and pretty much watching my grandmother die by inches (and my mother’s health worsen as we both tried to care for her until the end came). My life had hardly gone how I’d imagined or hoped it would have, and still hasn’t. There were so many stories about time travel and altering history that I’ve seen that I didn’t bat an eye. But for some reason, that movie at that time made me so depressed that I was almost in tears. The characters are all down to earth and likeable enough (aside for Biff, one of cinema’s best villains, of course) and it seemed to twig on me that George was a hapless loser until he got a second chance through a fluke of science (and his cool son). I thought about myself and realized that I was similar – I was a hapless loser who seemed to be at the receiving end of life. I was bullied, and never stood up to the bullies out of fear in junior high. Women didn’t notice me and the few who did usually didn’t respect me. The confident, aggressive guys who walked all over me as a youth continued to do so as a man. I guess I related a little more to George than I expected, only unlike him…there’s no time machine in real life. I won’t get a second chance to fix the mistakes of the past. There’s nobody coming from the future to make sure I got the life I should have had or became the man I should have been. There’s no do-over, no retry at life and the hands I was dealt, or played poorly. I’m stuck as the loser I am, with the useless traits and tools I have, and there is no quick fix out of it. Even if I scrape together something better, it will never be anything like a happy, healthy, successful and romantic life. The fact that I never felt “the power of love” and likely never will didn’t help, either. I didn’t want to be stuck as the Dateless-Man, but it is how things shook out, and all I can do is trudge forward until it ends.

If I could go back in time and talk to my younger, pre-teen self, I’d tell myself so many things. Or, I might wind up acting out my own self loathing and muck up the time-stream. When I was 12, I’d have hated to be told by own future counterpart what a loser I’d be if I didn’t do this or that. I’d have also hated to learn that I’d still be messed up as a man over 30; at least when I was young I had hope that things would change. Now? There’s an eastern saying I like, “Hope is a bird with no feet.” It can fly, but never land.

Thankfully, today’s depression reminder didn’t last long. I’m over it, and I still have another essay about my latest go around with speed dating to type about. But since I have no other venues which I feel comfortable with writing about my bouts with depression and loneliness online than this blog, I figured this would do. At least this week I’ll hit my two posts a month average for October!

My longest term “female friend”

By and large I don’t like using the term “female” to describe a woman. It’s clinically true and I imagine its heavy use by those in law enforcement, science, and the military – and media centered around such figures – helped lead to it becoming part of the common vocabulary. It always seemed too clinical and robotic for me, even for someone as anxious as me. I sometimes struggled to come up with something more acceptable; as a teenager in college I once got roughly half of a “Psychology 101” class to all but glare at me by referring to women as “chicks” more than once. But, I use it here because the term “female friend” seems to be the one best used for the instance where a man has a friend who happens to be a woman. Because society at large (and by that I mean, mostly men) seem to pit the sexes against each other a lot and because it’s seen as rare when men and women can be friends without one or the other seeking something romantic directly, such a term remains distinct. It’s darker twin is the term, “friend-zone”, which I typed about disliking back in January.

Boy, did I allow that introduction to lead me off track a bit! Let’s start to get to the meat of it. This is an entry which I have talked up since the start of the year. It is the last major recollection of a dynamic I had with a woman during my past which is relevant enough to cover more than a paragraph. I saved it for last for one very key reason; it was easily the longest lasting dynamic I’ve ever had with any single woman who wasn’t family in my life, which dates back to the end of high school. As promised, the woman I have dubbed “Sonia” will finally be getting her own entry after her cameo in “The Everyone is Doing Better than You Party”. This blog is non fiction, but I have made some attempt to put some forethought into the posts so that they have some sense of flow or theme beyond the ramblings of a lonely madman. That’s the benefit of flashbacks, after all.

As with many of the people I’ve met in my life, Sonia was someone I didn’t directly seek out to meet, but was someone who began in the periphery of my social circle. She was the close friend, roommate, and occasional lover of the girlfriend of one of my pals. We met during one night where I and a few of my friends were just aiming to hang out and wander the area seeing what hit us. By now I was in my late teens and either completing high school or months shy of college, but since I was older than some of my friends they were still there. I was with two of my friends and we went to pick up one of their girlfriends, and her pal was tagging along. We hung around her apartment (in her room, mostly, as they played metal music on their computer and we chatted amid a few cats) and that is when I met Sonia. She was roughly 2-3 years younger than me, had several piercings, and her long curly hair was dyed either purple or red, I forget. She’s both Polish and Latin and is proud of her heritage, and her bisexual status seemed to be known almost immediately. She liked tight jeans, black nail polish, “goth” colors, and a lot of mascara and eye liner. I was in this odd position in that I frequently teased my friends for dating girls younger than they were by more than a grade, yet despite being of similar age if not older, I would have done the same had I been given the chance. In other words, I was a raging hypocrite then, although I tried to hide it (mostly by not being aware of it). I met Sonia and did what I usually always did at hang outs and gatherings – try to act all aloof and too cool for school while ultimately being a bit awkward and stand off. One example was by not sitting down while we were hanging out, so I’d be the only one standing. I would talk and joke around, but I usually tried to act like I was the sagely man of wisdom around my group – which usually came off as me being the stick in the mud.I don’t recall many specific exchanges during this meeting, but Sonia and I seemed to make a few exchanges with each other, as if she found me perplexing and didn’t quite buy the layer of baloney that I always projected. It didn’t raise to the level of “bickering”, but there was some ragging on me a little. Naturally, I found her attractive, and naturally, I made no attempt to betray any of this to anyone.

After a while we left the apartment and walked about a half mile away to a pool hall. I didn’t know how to play pool so I watched and engaged in the conversation as best I could. The hall also had an air hockey table, and that I knew how to play, so I engaged in a few rounds with one of my friends. A few hours of that, and we walked a few blocks further for some pizza and more neighborhood wandering before it was time to split up and go our separate ways. Sonia made an impression, although at the time she was only an acquaintance at best. Not long after another acquaintance of mine – a short long haired, bearded fellow who had earned the nickname “Jeebus” – was having one of his semi weekly binge drinking parties in the basement of an apartment building owned by his aunt. Most of us couldn’t legally drink at our ages, but that never seemed to stop anybody. It wasn’t my scene even then, as I didn’t care for it and felt it was not only a slippery slope of a crutch to rely on, but I found it aimless. Naturally, my friends didn’t agree and seemed to always want to encourage me to go out and drink more with them. On one occasion I went to one of those parties, and Sonia was there. As usual, there was a crowd of a baker’s dozen in attendance (if not more) and a lot of heavy metal music blasting from boom boxes. A small TV was on and “Robin Hood: Men in Tights” happened to be airing. This sparked a conversation between Sonia and I about a shared love of Mel Brooks films, and despite my usual sensibilities I’d had enough to drink that I was “buzzed” at the least, if not slightly tipsy. Sonia was just as far gone as I was if not more. As my friends used to say about me at the time, “When he’s drunk, the bug up his ass slips out.” Such a fact was likely proven true since I seemed to have no qualms about reciting many of the lines from “Spaceballs” (which is my favorite Mel Brooks film) that I knew from memory, which seemed to amuse Sonia. This second interaction with her seemed to go a lot better and we both seemed to enjoy each others company more. After a while the party ended and Sonia wanted to go with a group of them to a diner for food to sober up with. For reasons I forget (likely a lack of money) I opted to return home and cook my own food, but I hinted that I might try to drop by the diner later as they left. I made it hope and put on some hot dogs to cook, but I quickly fell asleep for a while and was only awoken by the burning food about two hours later. By the time I got to the diner they were gone, and I chalked it up to another wacky teenage outing.

I suppose this is as good a time as any to mention that Sonia had a “reputation” with some of the men that I knew. I don’t recall ever asking, but it being freely told (in low tones) to me by friends or other associates that Sonia was “loose” or “a slut”. This naturally meant that she seemed as willing to engage in sexual activity as is normal for guys to do; just as a woman (and especially one who was openly bisexual), she got more flack for it. Despite my hypocrisies, this was not a philosophy I believed in. I saw no need or fairness in denigrating women who slept with whomever they chose. These statements never shaped how I saw her as a person. I didn’t exactly stand on a soapbox and preach about feminist ideals as I avidly defended her honor, either. But I did not agree with or engage in that sort of rumor mongering. It was just noise I happened to overhear.

I actually got to know Sonia a lot better after talking with her online. When I got to college and had access to their library and computer labs, I got to spend a lot more time online than before. Before long I had my own username on AIM and through the social grape vine, Sonia got it. Less than a year later, she instant messages me out of the blue, and we began one of countless online conversations. She had moved to New Jersey, was going through a lot and needed someone to talk to, and had chosen me. I guess she had a positive opinion of me, and my efforts to come across as sagely seemed to sink in. In truth I always tried to be fair and helpful amid my sarcastic wisecracks when I could. I won’t go into the sordid details of Sonia’s life, because this blog is about airing out a lot of my baggage, not other people’s. The Cliff’s Notes version is that her past involves family turmoil, sexual abuse, and a lot of struggles with her self esteem and seeking the comforts of others, only to usually wind up mistreated or venting at them. Yet despite all that, Sonia often tried to have an upbeat and sassy demeanor. It was a past similar in some ways to that of my mother, which is probably a major reason why I try to have more empathy towards women in general. I became aware at an early age that they usually face a much different world than I did, even as someone who was bullied and didn’t easily fit in anywhere, either. It was quickly obvious that Sonia needed a friend to vent to in a safe manner who wouldn’t judge or reject her for it. I chose to be that friend to her, partly because by then my major was in “mental health and human services” so it was something I envisioned myself doing professionally. The other part is that I’m just that sort of goober sometimes. I never had a father, so it was those over the top good guys like He-Man or Spider-Man who filled that role, and I wanted to feel like I could save people (even if my world didn’t reward me for it as theirs did). And with that, our online correspondence began.

Not long into it, Sonia reminded me of that time at Jeebus’ basement when we bonded over mutual intoxication and a love of Mel Brooks. The added wrinkle was that she added quite a pivotal line, to the effect of, “I started to develop a bit of a crush on you.” It certainly surprised me, to say the least. It also wasn’t lost on me that she had phrased it in past tense. By this point she was dating someone and part of her current angst or turmoil, besides talking about her issues of the past, were issues with him. We talked daily or every other day for years of time. Even as the years wore on it was often once a week, or twice a week, or at furthest once or twice a month. Due to a variety of circumstances, Sonia moved a lot; typically to New Jersey (where she had family) and other areas of New York many miles (and hours) away from me (such as further upstate or on Long Island), since I can’t drive. Although she’s bisexual, she seems to prefer men, despite the fact that dealing with them can sometimes “trigger” her, among other complications. Unfortunately, like a lot of troubled people, she tended to fall into a lot of abusive or otherwise toxic relationships. It quickly became clear to me that I was one of the only friends she had who she felt genuinely listened to her without judging her or trying to get into her pants. Which naturally made me feel terrible every time I realized I was also attracted to her. I never mentioned it and I never acted upon it. She needed a true friend (among other things) more than she, or I, needed a lover.

Sonia would visit the “old neighborhood” now and then. One of the first time she visited during our online chronicles, she came with one of her friends, and we met up at Penn Station before heading back to the old haunts. Subsequent visits were usually more sporadic and unannounced. A couple of times, she’d turn up at a few bars where my friends and I were known to go on occasion on some of the rare occasions I was out with them. Her life always seemed to have a of tragic ups and downs. Every time Sonia would try to dig herself out, some new complication would arise. She’d try to go back to college, or to land various jobs or reconcile with her family, but things tended to not work out for her. Without a stable home environment for any extended period of time, it was hard for her to get out of certain ruts. I did what I could to help, but unfortunately there was a limit as to what I felt I could do. All I could do was try to be there for her online when she needed me.

About five or six years ago, Sonia settled (briefly) in an area somewhat closer to where I was so I could visit her on a sporadic basis. Once again, Sonia was living with another boyfriend, but this one seemed more long term and serious. They spoke of being engaged many times, and shared the same interests (video games, DC Comics, anime, horror movies, etc.). Sadly, as time wore on it became clear that this was another toxic relationship, although it reached a point where it was near symbiotic. As much as I liked being there for Sonia to vent to, I was always hesitant to give her advice many times. For one thing, she rarely asked for direct advance. For another, I always feared getting some situation wrong and being the cause of further turmoil if someone followed my advice and it didn’t work out. Secretly, I imagine that my own feelings for her caused me to second guess some of my own instincts. Could I accurately judge one of her relationships as toxic if I myself had feelings for her, even if I never acted on them? Besides, ending a toxic or abusive relationship is rarely so simple as to simply state what it is and tell one or both parties to leave. There’s entrenchment, there are deep emotions involved, and sometimes efforts to do so can wind up causing one or more people to dig in their heels. In the end all you can do is try to convince someone to see it for themselves.

Not long after she moved back to NY, I landed the job that I still have (as of this writing), I suggested that Sonia try for a position as well, since she needed the money and it was something she could do. She took me up on the offer and despite the long commute she worked for the company for roughly a month and a half through the end of 2011. Considering the ratio of male to female workers (with the men tending to be young), I did warn her in advance that while nobody would harass or trouble her, it was likely that someone would flirt with her at least once. Sonia was fine with this, as she seems to have a flirty demeanor herself. In an odd way, I probably should have warned myself. One of my co-workers (who then had seniority on me) developed quite a bit of a crush on her and even asked her out (which she declined), and she proved to be quite popular with the staff. Despite our long history as friends and my desire to keep it there, I’d be less than honest if I didn’t find myself becoming jealous for brief, fleeting moments. I never felt that way around her then boyfriend (who I’d met and hung out with a few times), perhaps because I knew of the sporadic turmoil the two had. For much of 2012, I wound up visiting Sonia at her place once a week (or every other week) to hang out, watch DVD’s or play video games, and in general to keep her company as her boyfriend often worked on the road for long, odd hours. Around this time they’d supposedly worked through their latest rough patch and were engaged once more. Yet despite this, they still argued and bickered quite a bit, and Sonia took to drinking more. Her boyfriend once said that, “You’re one of the only guys I trust to not try anything with her”, but his possessiveness usually couldn’t be hidden for long. Sonia would often defend him, citing her own temper issues and mental health woes. Once more, while I did my best to be there for her, and tell her that their relationship was toxic more than once, she had invested both time and what little money she had into it, and was reluctant to leave. I did have some temptations to throttle the guy, but of course this isn’t fiction and that doesn’t work in abusive relationships.

It didn’t help that while I had vowed to myself to keep things as platonic as possible with Sonia, that I had developed feelings for her over the years that I did my best to bury. Despite my long reservations about seeking to date someone who already has a boyfriend (for perfectly good reasons), I don’t know how I would have reacted had Sonia sought to come onto me or seek to initiate…something. More than once, Sonia suggested that I stay the night, since I usually left very late and mass transit from that area is spotty past midnight. I often refused, citing plenty of reasons while being mum about potential temptation for either of us. One weekend, however, I was simply in no mood for a walk and a wait and took her up on her offer. Her boyfriend was working an overnight shift and I knew that the risk for such a “something” was highest now. I suppose having feelings and conflicted emotions was normal, but I didn’t like that I had these feelings or conflicts, seeing them as a moral failing to even consider. It boils down to wanting to be better than most people, yet here I was caught between eagerness and dread that Sonia might seek to capitalize on the opportunity. Despite cheating on previous lovers (and this boyfriend being suspected of cheating on her, even as he was possessive), Sonia would have deeply regretted it and I like to think that had some sort of temptation happened, I’d have been the stronger, wiser man and shut it down. I like to think that, but I’ll never know. And I am glad I never got the chance; I wound up sleeping in a spare room abandoned by some roommates that’d skipped out on them, with a full living room and closed door between bedrooms. It was a restful night amid a bare mattress and oodles of cat and dog hair. Did I mention that Sonia’s an animal person? She almost always has multiple cats and a dog, if not more animals, anywhere she lives.

Sonia and her beau went with me for one of two days I spent at the 2012 New York Comic Con, which was a fun outing aside for yet another argument the pair had. When I was irritated with catching my friends having a laugh at my expense over my virginity on Facebook (“The Dark Side of the Internet”), I spent my 2013 birthday with Sonia and her boyfriend as well, and the three of us had a nice dinner. Not long after that, Sonia finally split from her toxic boyfriend and gave living with her family another go for a while. Unfortunately, that didn’t take and she’s currently somewhere in upstate NY with her newest fiance (and his kids, and her usual flock of cats and a large dog) and seems to be happy despite having to face more challenges to both her mental and physical health. We don’t talk online as much as we used to or I’d like to, and not for lack of trying. She usually doesn’t respond to private messages beyond a brief greeting, even though we interact via statuses and shared links almost daily. The last few times she’s sought me out that way, it was usually in hopes that I could wire her some money for some crisis or another; I never was able and she’s never held it against me, likely because I’d been willing to give her money (never more than $20-$30 at a time, and not that often) when I could if things were that dire in the past.

Sonia’s been slow to realize it, but she’s stronger than she realizes. She’s come from a lot of abuse, which sadly has not only taken a toll on her mental and physical health, but sometimes seems to be like bait for the wrong kind of men. These problems, as well as the difficulty she has settling in any home setting (either with family or a lover) for longer than a couple of years makes continuing her education or keeping a steady job difficult. Despite all this she is at heart an upbeat person, and tries to acknowledge her bouts with depression head on. She’s very beautiful, although she’s always been waxing and waning between struggling with her weight and being proud of her curves. If someone asked her what kind of friend I was, she’d probably offer a laundry list of compliments; meanwhile, I wish I could do more. We’ve grown up from teenagers to being in our 30’s and shared a lot of emotions together, her more than me. My vow to be the one guy in her life who was willing to do right by her without wanting something romantic in return hasn’t been easy, but maybe integrity never is. I’ve never shared my feelings in the past with her, and at times Sonia has wanted to help me move on with my own love life – she once offered to set up an OKCupid account for me or critique my current profile (which I barely touch). Sonia isn’t the only “female friend” I’ve had for over a decade, but she’s the only one in which my own personal feelings shifted beyond being platonic for moments here and there.

Whatever romantic love is, I wonder if I got close at times regarding some of my feelings for Sonia. While I have tried to avoid waiting for “the one” in terms of dating, there have been moments over the years where I wondered if Sonia was my “only chance”. At least one of my friends tried to talk me into making a move with her over the years. At a BBQ several years ago, my pal M*** (another reoccurring figure in these posts) seemed to have been inspired by being at a bar and seeing us interact when Sonia came by for one of her sporadic visits. The two of us were leaning against a fence and M*** and he was convinced that she had feelings for me and said in no uncertain terms something to the effect of, “If you don’t make a move, maybe I will”. He wasn’t the only friend to make that suggestion regarding her, and my answer was always, “That ship sailed”. Sonia seemed to always be in the midst of a relationship when we’ve interacted, and her relationships have been getting longer as she has matured and sought to settle down. She deserves far more than to be the first stepping stone to anyone’s romantic voyage and she also deserves someone who has far more to offer than I can, especially in practical terms such as having a car and a larger place to move into. There were times I was in turmoil over stifling my own feelings, and even envious of some of the men who were dating her during my 20’s. Fortunately, I overcame those feelings without dumping my baggage onto her and without mangling our friendship.

I suppose this could be an extended case of how timing can really be everything. Maybe had I hung around her more when both of us were teenagers, and maybe if “something” had happened then, things could have been different. I certainly wouldn’t be the Dateless-Man. Yet on the other hand, maybe all of the teenage hormones and drama wouldn’t have done either of us any good. Maybe things could have gone wrong and we’d not have been friends for as long. As some recent Disney films are seeking to ingrain into kids, not all kinds of love are romantic. The love between friends can be just as important, at times more so, than romantic love. I merely wonder about things, rather than have any regrets, in this matter.

And this is it. In terms of substantial flashbacks regarding the women in my life who weren’t family, this is really the last one I can think of. Naturally I don’t have total recall of every interaction I have ever had with someone of the opposite sex from birth until now, but this is the last of the series of flashbacks which I felt had any weight or shaped my outlook on things in any way. Overall I see this as a success, although not exactly the way some would expect. Sonia’s life has been full of tragedy, and I am glad to have been part of an element that wasn’t. And in a way, she’s been there many times for me as well; simply by being a woman who is willing to talk to me or who considered me a worthy individual for even a moment puts her in very rare territory in my life. She really is the total package despite any “flaws” and I am glad she is closer to seeing that in herself now than when we first met. It simply is a shame that I couldn’t have met even one or two other women who offered at least half of what she did in all of these years. Maybe then I could have been a normal person and not, well…the Dateless-Man. But, if this narrative proves anything, it is that for good or ill, life is rarely what you plan for it to be. Perhaps had I not suffered and been alone for all these years, I wouldn’t appreciate the suffering and loneliness in others.

Not surprisingly, this has also been the longest post I recall doing, covering many years of time. There’ll be at least one more entry coming; either a recap of the comic con speed dating in a couple of weeks, or a recap of why I flaked out on it. After that…who knows. It has been quite a journey and quite a lot of typing. It’s been good to read and reread these entries as well as the wonderful replies I’ve gotten from them and evaluate things. I can’t say I have reached the level of zen that I’ve hoped for yet, to be absolutely free of all emotional romantic desire, nor have I decided to take more swings at futility on a regular basis. There is more to life and more to do in it than being angst ridden over my lack of romantic success.

To date, she’s been the only person who wasn’t family who I have ever shed tears about. As a man, even admitting something like that in text feels like a weakness. No matter what happens, she’ll always have a special place in my heart.

A baby step back to the future

Believe it or not I do try to average at least two blog posts a month (with occasional spurts of more), but it seems that I did miss that schedule again. The reason has been a mixture of my work schedule (both my day and night job and hobbies) as well as a general sense of malaise. I think such a sense has been obvious all summer, now that I look back. Two out of my last three posts have been dealing with my angst of being an older male virgin; after all, I am even more “over 30” this year than I was when I began this long term recount of my dating failures. As I have stated before, I feel myself at the center of a crossroads between giving up on dating forever (or at least the near and incoming future) versus making one last desperate push based on absolutely nothing logical. Usually the months between March and October are the months where my general sense of depression decreases. I am hardly depressed, but I simply feel a sense of being adrift in a lonely ocean and wondering whether it is worth it to strain my arms in futility trying to pick a direction in this matter or to simply continue to allow the tide to take me.

I know I am not an ideal lover or date for most women around me. I know that I have very little to offer either physically or in terms of charisma. I know that I have no end of esteem and emotional issues, as well as plenty of real financial and even family worries to juggle as well. My mother’s long term health is rarely good, after all. On the other hand, I am not getting any younger, and as difficult as all this is now, it will be even harder when I am “over 40” or beyond. There are no end of men going through just as much as I am or worse who don’t give a damn about dumping their problems or issues on women in their quests to get laid; why must I be the lone hold out in the universe? Sure, I may have integrity, but that doesn’t keep you content at night for long. My ideal to quash the very feelings of loneliness doesn’t seem to be entirely and permanently possible without some outside substance or horrible brain injury – neither of which I desire.

The truth is that I have been in the middle of a period of “giving up trying” in terms of romance for at least six years. My 20’s faded away and now I am where I am now. And the more I mull over options and worst case outcomes, the more time I may be losing. There is a part of me that wants this, that wants all of this stress and self mourning to be over. But there’s this other part that still wants to try and succeed at this, despite the mountain of evidence I have complied in the installments below which state fairly clearly that I am not cut out for this. I’ve had few genuine opportunities at romance. What opportunities I had I botched so spectacularly that it took me years to realize it. Yet despite all that hindsight, I likely would screw up again if I went at it again. There’s no reason why I should believe otherwise. If there is one lesson I have learned in life, it that regardless of age or setting, no woman I have ever had even faint attraction towards has ever been interested in me in any way. It may as well be an enchantment on my flesh.

But, I have taken a baby step forward. Like most people, “putting your money where your mouth is” can spur at least some motion. I’ve been mulling “investing” some small amounts of money into opportunities which have come up in regards to dating. One of them is going “premium” at OkCupid (one of the internet’s biggest free dating websites which I rarely visit and in which I got exactly one date with nearly a decade back) to look at the 25 women who clicked “like” on my profile (who for all I know may no longer be on the site). Another was signing up for an annual speed-dating event at this year’s annual New York Comic Con, which I have been attending ever since 2011. I’ve done speed-dating before, but this time promises a collection of women at least modestly (if not heavily) into the same geeky crap I am into. It’s an event which usually fills up weeks before the actual con, so time was of the essence. Yesterday, I plunked down my $20 digital dollars and signed up for the latter. So, almost six years after my last speed dating event, I have decided on that as my first foray into the realm of potential romance once again.

The con alone will be tiring, especially since I usually get little sleep beforehand preparing for it (atop of my usual work schedule). Speed-dating can itself be exhausting; it feels like dozens of job interviews at once. I could always flake out between now and the event itself and just decide to eat the twenty bucks and not bother. There is the chance that some “once in a lifetime” event or signing or panel could have happening at the same time and I have to choose. But, the very act of committing some (green) skin into the game at least makes it more probable that I will go through with it. So, at the very least, I will have another post coming next month.

Part of the dilemma is that as I am utterly inept at going with the flow or capitalizing on a crumb of a chance, I attempt to overcompensate by over analyzing things in advance. I call it “prep-time”, a term some fans throw about to explain how Batman can beat anyone given enough time to prepare. And part of that is trying to prepare myself, at least emotionally, for all of the worst case outcomes at once. And I realized that even if things go well with a woman, that doesn’t lead me towards any happiness; only another awkward moment and more potential for yet another deflating and frustrating outcome atop of all the others I have had in regards to dating. Say it goes well, I get a date. The date goes well, eventually I have to try to go in for a kiss. I’ve never kissed before, so naturally I’ll be terrible at it since I had no practice. A poor kisser is a mood killer for many women, and not for any unfair reason. But say that goes well and we have more dates; then I have to make further moves, or at least explain why I am not bothering while still projecting interest. Even the very notion of admitting my interest in a woman directly to her feels…off. I’ve literally never done that. I have literally never said or typed or communicated to one of the women I have ever liked, “I like you, I think you are beautiful/intelligent/etc. and would like to continue whatever”, not once. I always knew the outcome or feared it. I can’t imagine even taking off my shirt before a woman, what with the large lipoma on my back and a wart near my nipple, without imagining her even vomiting or sending me fleeing into the night with thrown objects. I simply cannot be that charming or handsome face wise towards a woman to compensate for this; and if I was, that would only cause me to become more suspicious. All this mental drama before I’ve even sat down and rotated or sent out an IM. You can see why I don’t want to bother anymore. It’s a mess for everyone.

At the same time, living in endless fear and underachievement doesn’t feel any more secure. The safety in endless misery only lasts so long. So, a baby step in one direction. We’ll see how it goes. I expect it to go poorly and be underwhelming. I doubt I am any more appealing to comic con women than I am to “average” midtown Manhattan women.

I do have one more past adventure to recount, which by now I have likely built up more than I can deliver with. I will get it typed eventually. I do think it is a doozy. But, all for another time, and another lonely night at the keyboard. Thanks for reading.

Dateless-Man vs. the Vicious Virginity Cycle

Ready for some more whining about my v-card? Honestly, this wasn’t a topic which I expected I’d devote some 2-3 entries for, if not more, when I began this blog last summer. It was likely inevitable as I would run out of previous adventures to discuss, and would have examined all of my major past encounters with women in time. Despite the title, I am very aware that all of my problems with dating, or life in general, won’t be solved by grinding flesh with another person in the end. However, I do find himself in a bit of a cycle lately when weighing any options, and while it may not be entirely due to my most shameful secret, it certainly is a factor of it.

In the end it all comes down to a lack of experience. It can feel very much like seeking employment in that way. Most employers prefer someone with experience – whether it’s gigs one needs a degree for or even slinging burgers for minimum wage – yet it’s hard to get that experience if no one hires you. And much as with that situation, age and assumption by society also play key roles. Most employers would be sympathetic to a teenager without any job experience, but someone in their 20’s or 30’s would be seen as odd (in the least). To a degree dating is similar. Like with anything, dating, sex, relationships and love are things that are skills which can be learned, so long as one has opportunity. Without that opportunity, however, the odds of landing any “positions” (pun intended) become nil. Much as with employment, the older one gets without a certain level of experience, the more bizarre it seems to others. Reasons don’t much matter; few people genuinely care about such things. In a world built on endless competition, especially with men against other men in nearly anything, reasons for a lack of certain skills are ultimately meaningless. The world doesn’t care.

Virginity as it is known is a social construct, invented by men eons ago for various purposes, least among them controlling women’s sexuality to make the task of figuring out whose children are whose (often for the sake of inheritance) easier. It, along with other gender norms, effect and hurt both sexes in different ways, although there is some overlap. It can seem that too many people – especially men – can make too big a deal of it online too often.

At the moment I feel I am at a crossroads. There is a part of me who wants to look at the body of evidence laid forth in this blog, see it for the litany of failure that it is, and move beyond it. Call it exhibits A thru Z as to why I need to embrace my inner zen and abandon even the theory of dating anyone. It is where I, intellectually, want to be. I want to be able to give up on this and never feel any pangs of being lonely or envious ever again. To be freed from such desires and continue on with the rest of my work, such as my job, my family, and my hobbies. There is another part of me, however, that doesn’t want to quit; that insists that my last date was some seven years ago and despite my insistence, I’m not the same as I was then. I consider this an emotional side, as it ignores all previous examples of my dating futility and seems to still hold to an ember of hope that things will be different were I to try again. The struggle of the heart versus the mind is a classic one, and to a degree it is one that we all have to weigh about a variety of things. There seems little way to reconcile this personally, at least at the moment.

Onto what I have dubbed, the “Vicious Virginity Cycle”. For most “normal” people, the path of romantic relationships is one of youthful experimentation which leads to trial and error and hopefully, a final partner whose selection represents the culmination of all that has been learned (or not learned). You stumble and bumble during teenage years, refine skills and desires as a young adult, and by the time one is in their 30’s, one is supposed to at least have a better idea of what they want in a lover, what they won’t consider or accept, and more importantly have enough pieces in play to want to share them with someone else for a longer term. This includes having been through (and survived) at least one break up, which tends to go better the younger one is, as teenagers rarely have enough resources at their disposal as adults do when it comes to grief. For an older virgin, they have no such experience, and the lack of it not only makes it difficult to venture forth at a later stage in the game than their peers, but it also makes their peers hesitant to risk becoming part of a late bloomer’s bumbling quest.

At my age, most women where I am in New York are seeking to settle down with someone for the long haul. Hell, even in college in my early to mid 20’s, most of the women I encountered seemed to be looking for long term relationships over flings (or at least so they said). And while I am not exactly looking for “one night stands”, I also cannot honestly say I am looking to “settle down” and marry yet, either. My love life hasn’t even begun! And this represents a dilemma for any woman who would even consider giving me a chance, so long as she has full knowledge of my terrible secret. I cannot look someone in the eyes and honestly tell them that I love them and want to spend forever with them if they are the only lover I have ever had, the only woman who dared embrace the beast, because I have no frame of reference to compare her too. In addition, any of the mistakes and errors that are common in first relationships would be hers to suffer, at a time when most women hope to have left that sort of thing in high school. Therefore, a woman would be reasonable to assume that after I had my “first time” with her, I likely would not be staying with her forever, and would ultimately move on. This isn’t to say that I want to “love ’em and leave ’em”, but without a commitment, a break up is inevitable. What woman would want to be the stepping stone to an old hapless virgin’s journey? It’s an unfair thing to ask of anyone, much less someone that I may happen to like.

Most normal people don’t go through angst like this, because they did all of their “experimenting” with their physical and emotional romantic needs during their teenage years. Going through that again with someone who is old enough to have acquired this experience is not something which I imagine is desirable. This, therefore, would favor a woman who isn’t looking for long term romance but is after shorter term flings herself. But, this represents another problem; a virgin, by definition, is inexperienced and therefore can’t be counted on to please even in the short term. I can’t even be counted on as a boy toy, a friend with no benefits. I, of course, having had no experience, would be tickled pink just to make out with someone. Alas, that leaves the woman with nothing gained on her end, and that’s an unfair proposition to put on anyone. I suppose I could be delusional and assume (or hope) that by sheer fluke I am some sex prodigy who somehow nails everything on the first try, but I sincerely doubt that. Life isn’t that convenient, at least not for me.

So, in conclusion, being an older virgin means that I have nothing to offer a woman with long term goals (as it’s likely that she would merely be “the first” and not “the last” for me, even if I decided to marry my second girlfriend), nor do I have anything to offer one with short term goals (as a man who has never seen a live vagina is likely to be a terrible short term lay). I don’t believe I project an aura which screams of “danger” to women, but that alone is the bare minimum, not a plus. Outside of high school, there are no accepted ways to safely “experiment” with anyone aside for sexual surrogacy or prostitution (which outside of Nevada is illegal and dangerous for women).

This paradox makes it difficult to even fathom trying to date anyone again intellectually. In order to have success I have to project a sense of confidence and self, and that I have something to offer. Even faults should, in theory, be spun in ways that can be seen as strengths. However, there is no positive way to spin being an inexperienced virgin over 30. There is no way to sell that to anyone in a manner which is anything short of desperate or pathetic. There is no way to have confidence in an area in which you have never succeeded before. What would I have to be confident about with a woman? What reason could I have, what could I possibly offer romantically that she couldn’t literally get from literally any other living man within a mile radius? It is delusional, and unfortunately that is something I am not. And the longer one stays crippled with inexperience, the harder it is to risk trying to get some. Hence, a cycle. I have a sense of humor, but that alone isn’t enough; you don’t rack up “joke points” until they reach a certain threshold and then you become “sexy”, same as simply being “nice” should carry no expectation of romance.

And this is a cycle which can easily make the decisions as to which side in my crossroads to take for me. I have some potential opportunities online. I could invest more in OKCupid, pay the $10 and get to see the 25 women who clicked “like” on my profile (whose profiles weren’t ones liked by me in the past). There is a speed dating event at this fall’s New York Comic Con which I could, in theory, apply for. Speed dating is vastly tiring and a convention is tiring enough, but how often does one get to meet women who will all likely be into similar geeky stuff that I am? And there is one acquaintance, a literal friend of a friend, who I have gotten to know slightly on Facebook (as in, we are friends and comment on stuff sometimes) who I would love to date, had I anything to offer besides being the low earning rung of a romantic ladder. But even when I begin to consider potentially trying for any of these options, I face the cycle (or “the Self Awareness Paradox“). Putting a bow tie on a farm animal won’t make it a man, and unfortunately, that’s all I have. Hiding it didn’t work and any romantic foundation built on lies doesn’t work. Unfortunately, there seems to be no honest way to escape this cycle.

The best I can do is to try to erase any desire to do so from myself. Maybe one day, I will succeed.

Sorry for the repetition. Maybe I should get to my last flashback and get on with it already.