First dates and “Double Jeopardy” – The High School Adventures, Part 2

It’s been the longest gap between posts that this blog has seen, which means it’s time for another previous adventure in the life of Dateless-Man. We’re still in the midst of my high school years in the mid to late 90’s and this chapter should hopefully be the meatiest in terms of the blog’s stated purpose. It’s time for dinner and a movie, or just one of the other – it’s my first date, in all its’ awkward and mixed message glory.

Picking up from the last “high school adventure“, I was now a teenager in the mid to late 1990’s, a rebel without a cause and a loser without a love life. By this stage I was skipping most of my classes in favor of hanging out on campus with my clique of friends (mostly freaks, geeks, goths, stoners, and metal heads) either shooting the breeze or playing table top RPG’s – character sheets, dice, and all. Most casual observers thought were were gambling until they saw the d12’s. Naturally my mother was far from happy with my truancy, and this led to some of the worst arguments of our lives. I just didn’t give a damn and considered myself a bit too “cool for school” – which was ironic as I wasn’t too cool at all. At any rate, I did attend some classes here and there on my schedule, and at one point that included a social studies/history type class in my sophomore-junior year. The teacher was an older and sterner man who I would later revisit when I finally had to get my GED, but that’s another story.

In a way, the genesis of my first date is a perfect microcosm of my relations with women in high school, and perhaps later. Naturally, as a horny teenage male with zero confidence, I spent many classes sneaking peaks at an incredibly attractive young lady who was seated across from me who I in no way had the guts to ask out. I would still interact in class, and despite my truancy I always proved to be an apt student when I bothered to show up and study. But I imagine that a good reason why I still attended this class was due to the object of my desires. Awkwardly, one day I found myself handed a note in class not by her, but by another young lady who was seated next to me, who I’d hardly noticed. Yes, this was the era before texting became as widespread and kids still passed notes on paper to each other. Is that something that still happens now?

As always, all names are changed to protect the innocent; I’ll dub her Sophie. For the record, the names I choose to dub the ladies who are involved in my misadventures are chosen based on the first letter of their real names and then any alternate name which pops into my head. I’d noticed her in the class before, but she simply hadn’t been as glamorous as the girl that I had been obsessed with in the class. Yet she was still very much “my type” and appeared friendly. To be blunt, my initial response to being handed a note by her in my class was surprise. It was a very direct note, asking me whether I wanted to attend a movie that weekend with her, which literally offered check boxes for “yes” or “no”. Rather than leap at the chance, I was stunned that she was offering it at all; by then I’d had no luck with women and was suspicious and hesitant of disappointing any who had been near. I recall my initial response was writing in a “maybe”, and asking about more details.

This wouldn’t be my last date, but every time I am on the cusp of one, my lack of confidence manifests itself sort of like a disclaimer. I usually display surprise at being the target of a date as well as ask the lady some version of, “Are you SURE!? Is this not a GAG!? You DO know you’re asking ME out, right? The lowest rung on the man ladder! Don’t say I didn’t warn you if you’re disappointed!” Considering how many girls by then had played the “she likes you game” with me or previous experiences involving cruel pranks or tricks, maybe some hesitancy was justified. As a teenager, I was far more cynical and wary of things than I had been in elementary school (even if still more hopeful than I am now). At any rate, soon the details would be ironed out between Sophie and I. Date, time, which theater, which bus to take and so on. From the onset, however, Sophie seemed to stress one thing: “We’re just going as friends”. She said it when we met that day, she said it when I called her to confirm it, and on the evening of the date itself. “Just. As. Friends.”

So, I did what any logical person would do. I took her for her word.

Naturally, I made sure to be perfectly cleaned and shaved, and wore a nice button down and shoes. My mother was thrilled that her shy son was finally on a date. And things seemed to go well. Sophie and I chatted on the 45 minute bus ride to the theater we wanted to go to, mostly about shared tastes in movies and other small talk. She enjoyed “smart action movies” the best, and in addition to being a Russian immigrant, was taking a gymnastics class at school. The film we wound up seeing was “Double Jeopardy”, starring Ashley Judd and Tommy Lee Jones. She’d seen it before, but wanted to see it again and I was certainly game; considering it was my first date, I’d have been game for “THE CARE BEARS MOVIE” if I’d had to. I remember that we decided to go dutch, but I was such a bundle of nerves that I almost forgot to go up to the ticket booth and pay. I don’t remember if she got snacks or soda or not; I know I never went for that at the movies and still don’t. Any any rate, there was the two of us, in a darkened theater watching a movie on the big screen.

And that’s all we did; watch the movie.

I never made a move, never even tried to flirt with her. It wouldn’t have helped had I tried, since I in no way would have known what to say or how to deliver it. I recall during a love scene with Judd in the beginning having an odd feeling about me, and glancing back at Sophie. She looked back at me for a moment and I distinctly remember debating within my own mind to attempt to make some sort of move, or not. My best option was also the most tired; the “oh I am yawning oh look there is my arm going over your shoulders by sheer accident” move that I likely picked up from TV somewhere. It would have been lame; even I thought so. I didn’t want to make Sophie uncomfortable or cause her any sort of distress or a bad time; in fact, throughout the date I stuck to my usual routine of trying to make her laugh with quips, which is how I usually interact with people. So instead I respected her decree; that we were “just friends” seeing a movie. And lord knows I’d never tried to make a move or romantic suggestion to any of my other (male) friends on trips to the movies. So the moment passed, and soon the entire movie did. I did enjoy it, at least. Our hands stayed on the armrests, our butts in the seats, and beyond some banter we mostly watched the movie in silence, as instructed by the animated figures at the start of any cinema experience.

The bus ride back seemed to go faster, with there being slightly less banter. I was still inĀ  a good mood and Sophie seemed to, as well. I walked her home (as she didn’t live too far from my apartment), and the date ended with a hug and a “we’ll do this again sometime” statement. We chatted for a few minutes after on her porch and I was thrilled. Was this the start of something? What would we do for the next time? Did she really like me or was this just a “friendly” movie trip? Naturally, by our next class I was asking about our next date, and Sophie said she was busy. Then, she had an accident at her gymnastics glass and sprained her ankle quite badly – bad enough that she had it wrapped and traveled with crutches for one or two weeks. Sophie insisted that she wouldn’t go out again until she’d recovered, and I certainly respected and understood that. I tried to be a gentleman to her, help her with books or doors before and after class, usually walking her to her next one. I would call her on the phone, but she almost always cut our conversations short.

After a fortnight she was only using one crutch and not long after seemed to have mostly recovered. I began asking about when she felt she might be ready to hang out again, which she kept putting off, saying she wasn’t ready or was busy. I respected this and tried not to badger her, and gave her space. However, one day in class she was chuckling with some of her friends and I learned that she’d been busy with them, going to the movies and doing other things despite her ankle. Her ankle was soon healed but Sophie continued to give various reasons why a second date wasn’t on her schedule; a test here, something else there. Yet the next day in class I’d always find out that she’d instead been busy with her friends. Any phone call (which was maybe once or twice a week) would end quickly, until the point where she stopped taking my calls. Eventually I caught on that she wasn’t interested in another date, but hadn’t told me in as blunt a way. After about a month or so, then, I stopped trying, and she made no move to suggest this distressed her. We remained friendly, even after the class had ended if we bumped into each other in the hallway, but usually not more than a “Hi, how are you doing?” sort of deal.

So, that was my first date experience. No flowers or candy, no fumbling hands or lame passes – just a bucket of mixed signals on both ends. I imagine responding with an opening “maybe” started things off on the wrong foot, and her insisting we were “just friends” was either a tactic to ensure I didn’t get grabby or some counter-measure to that. I never would have gotten grabby or crude, but naturally there’s no way Sophie knew that, and I imagine most young women try to set boundaries for their safety. On the other, I never quite understood why Sophie didn’t simply tell me how disinterested she was in me after our date, and allow it to end at that. Years later I reasoned that women often do that because men can (and do) become nasty or even violent (or stalker-y) when they are firmly rejected. I never would have done so, and while I would have been a little deflated I’d have merely internalized it and moved on; but again, there was no way Sophie knew this. Still, I prefer a firm statement of displeasure rather than a promise of a new date or a claim of having had a good time when clearly, that didn’t happen. I mean surely if I come off as enough of a putz to be unworthy of a second date, I also come off as a putz who’d never lay a hand on a woman even if she’d stabbed me. In the end it came down to me having no charisma and never making a move, so I imagine Sophie lost whatever passing interest she had in me romantically. That or maybe she just really did want company to see an Ashley Judd movie again.

At the time this wasn’t a huge deal; I was disappointed but bolstered by my experience and imagined I’d learn more from future dates with future women. Little did I realize that it would be at least six years later when I was in the midst of an extended tour of college before I’d get a date again. I had no idea that my dating opportunities would become more rare than sex between Vulcans. While I was a cynical and frustrated teenager, I still had hope for the future, hope that I’d encounter young ladies in travels and exploits with my friends much as they had. Hopeful that something would happen, that someone would take an interest in me; after all, it’d happened once, right? Eventually that hope died as the years went on, and the cynicism and frustration would only grow.

I can count the amount of formal dates I’ve had on one hand, and still have fingers left over. Much like a lot of things in my life, this first date seemed fun on the surface but beneath likely had a lot of misunderstanding and missed cues on my end. I want many of the same things normal guys want, yet when given the chance I often have no clue of what to do and bungle it, missing some unspoken hint or trigger that is common for everyone else. Maybe there was nothing I could have done back then, as respecting a woman’s word and choices about what she desires from an encounter has usually always been my policy. Unfortunately, obedience is not very attractive or charismatic, or adventurous to a woman, whether in the 1990’s or now.

Still, most people’s first dates are awkward horror shows. And at the very least, a minor film like “Double Jeopardy” will always have a place in my memories and my heart.


Another summer of discontent

One good thing which has come out of this blog for me is in listing some of my past experiences alongside my more current rants and feelings, I get the sense of things working in cycles. Some cause and effect. Much as in high school, I remain a third wheel in the romantic subplots of others, always on the outskirts but never in the middle.

Summer in New York is always a season where love, or lust, seems to be everywhere. The weather is warmer so people are wearing less. Trips to the beach or at least general outings for couples are more common. You can hardly take a bus or a train or even a walk anywhere without encountering a couple, often in mid-smooch. Like most people, I tend not to be fond of public displays of affection which don’t include me (same as many people dislike any wedding which isn’t their own). It naturally doesn’t help when it seems left and right, all of my friends one by one are either getting married or getting engaged or seeming to go steady with someone, almost all at once. Even co-workers at once seem to have been struck by Cupid’s arrow. To heck with Hallmark and February, I say summer is when most people get bitten by a love bug. Everyone but me, always a day late, a dollar short, and dressed in the exact wrong attire for the party.

In my second post (“I am tired of being Jacob Marley”), I mentioned my current job setting vaguely as well as the fact that I seem to have accidentally begun mentoring a younger coworker as an impromptu sidekick. This wasn’t deliberate, but as most people do at work, I’ve gotten chummy with some of my coworkers, especially since we all end up sharing the commute. Among the coworkers who have become part of our troupe are an older couple in their mid to late 60’s and a fellow I’ll dub Hal. He’s in his 40’s and is a hard worker, but also easily angered, long frustrated, and with a few screws loose. No matter what, he always seems to have this personal “musk” about him. He’s tall and I suppose his looks could be considered “rugged”. In terms of demeanor, it’s akin to taking the DNA from Edward Norton from “THE HONEYMOONERS” and Eeyore from “WINNIE THE POOH” and splicing them into some clone creation. I’ve long tried to encourage him to take things easy, to help him do a better job, but there’s no getting through to Hal.

At any rate, as it happens, a new employee has once again joined our ranks, a part time teacher in her 20’s. She began sharing the commute with us and for a night, I was beginning to wonder about how she felt about some of us. She smiled at me a few times, and I would try to smile back, and she would lower her head, as if embarrassed. We even talkedĀ  a little! I am not a good student of body language, but is this attraction? She is my type, but I have long abandoned pursuing people of my type, as I assume I have no chance because they don’t notice me. But did she? I’m the reverse of most men in that while most men seem to assume any woman who looks at them is into them, I go out of my way to explain away any sort of hint at someone simply being friendly, or it being happenstance, or mistaken circumstances. In fact, this post may have been very different had I typed it sooner.

But at the end of today’s work shift, something changed. It was still the same stuff from this new lady with the group’s ride home on the trains. We even talked more. However, the older couple seemed to notice something I had not – it was Hal she was apparently making googly eyes at, not me. The fact that he was dating someone else – a woman in her 40’s or 50’s – didn’t seem to matter. Hal seemed to enjoy the choice of two women in his life. For the life of me I don’t see the attraction, but then again I am neither a woman or into men. Hal is tall, at least, although his body odor and temprement often make me seem together.

It was another instance where I was merely a background figure in the soap opera of someone else’s life, and why I should never even entertain certain possibilities. Even after so many adventures, so many failures, so many confirmations of my datelessness, for a moment I forgot I was the Dateless-Man, who nobody is attracted to, nobody is into and nobody loves romantically. Next to me, even someone as screwy as Hal is a stud in comparison. I should rent myself out as a wing man to malcontents – I’d make a killing.

The only saving grace is I didn’t make a move and embarrass myself, especially with a coworker in a small, gossipy office. I am at least used enough to my burden to avoid such mistakes.

And so another summer comes and goes, with the birds and the bees in the air for others, but not for me. My job is only to observe, and wonder how, and why, and what I don’t get.


Oceans of advice, and too few solutions

One thing that will come up the minute you either let it be known that you’re dateless to any circle of friends in real life, online, or any other place will be advice. Hell, dating advice is none too rare online; just Googling it will produce nearly 30 million results! They will range from mainstream magazine articles or book shills to people running online columns or message board topics, to even videos online. Everyone and anyone seems to have some magic answer for why you (or I) haven’t been able to find that special someone – or any someone – and get out into the pool. Whether you log in to commiserate with the masses at or send an email to the Playboy Adviser – two things I did in college – you will be swarmed with a sea of advice from experts to layman.

The one thing I never found was answers. I really do wish it was that easy, or it that simple. But the bottom line is everyone is unique, and that means every screwed up person is screwed up in a unique way. The path that made me the Dateless Man wasn’t a simple or static one.

I figured for spits and giggles I’ll bring up some of the most common or memorable bits of dating advice I have ever gotten from friends, family, strangers, articles, or emails and why they didn’t click for me. If some sound like cliches, well, that’s only because many are. We’ve been bombarded with so many sound bite morals in fiction and media that few of us even examine what they mean or even if they’re universal.

“Just be yourself.” – It sounds so simple and obvious, but it’s not. What if you don’t know who you are yet? And what if “yourself” is a terrible, lame, or otherwise non interesting person? Really, this advice just sounds like, “keep doing what you’re doing longer, and it will work out instead of defining insanity”. After over three decades of being myself, I am pretty confident that who or whatever I am is not attractive romantically to anyone that I am into.

“Pretend to be someone else until you learn how to do it.” – This is usually followed about how it’s all part of “the game”. Why does love or dating or relationships have to be seen in the prism of “a game”, as in some sport or contest with a winner and a loser? In effect, this is acting, whether one pretends to be someone else completely or just “fakes being confident”. In the end, this is lying to someone as a first impression, and I’ve never felt that’s a good place to start any relationship, casual or deeper. I know that none of us reveal or act like our true selves in every social or professional setting – and most times we shouldn’t – but shouldn’t dating be different? Besides the fact that I am no actor, I always felt it would end poorly to pretend to be someone else to a woman, and then inevitably have to disappoint them later on when the act has to end.

“Date younger women.” – Unfortunately, I never felt any attraction to “jail bait”. One disadvantage to getting older is that it does change the dating pool one can partake in, which can become a problem in a society where women are essentially manipulated into growing up faster and told to dress as sexily as possible for men’s benefit – even while children, and even while then hypocritically being judged for such things by the very men they’re told to entice. I usually have less in common with younger women, and often feel like cradle robbing even considering a woman who is too young. Age 18 is “legal” and 21 is “old enough for bars”, but even women around that age seem too young for me, and I would feel like a dirty old man even attempting to date one. Heck, sometimes a 23 year old can seem young to me. To switch the P.O.V. a bit, most younger women are into “older men” besides on maturity, wealth, access to things like homes or vehicles, and social status when compared to peers. I don’t have my own place, or a car, or much money, or even a good job. I imagine there are plenty of 17 year old dudes doing better than I am. And at least some of them have a future.

“Date older women.” – Besides the fact that some women past a certain age (not all, or even most, but some) are not my type, my biggest worry here is getting involved with someone who wants to “settle down” and get married, when I am nowhere near that stage. Why jerk them around? To switch the P.O.V., most women who date younger man, besides for companionship, do so because they’re seeking younger studs to instead of the older men in their age range who may need pills to make anything happen. I am nowhere near attractive enough to fill that role.

“Ask out women you’re not into to build confidence.” – I have debunked this a few times in previous posts, but I may as well bring it up here. Usually, it’s men who bring up this advice, usually by switching out some words I used and adding ones like “ugly girls” or “fat girls”. Frankly, I find this entire line of advice to be cruel and demeaning to women. I am past the stage in my life where I would ever feel that just because I am not into a particular woman – that she isn’t my type – that she deserves to be used merely for my own “experience”. I don’t like “using” people, period. I know what it is like to have my emotions jerked around to someone else’s benefit, and I’d rather not ever do that willingly to another person. The worst case outcome of this would be a woman I am not into falling for me when I am merely exploiting her for my own personal “confidence”, which leads to a heart breaking ending and a lot of bitter resentment. Honestly, men who do this sort of thing are part of why many women are wary of them or hate them (beyond the whole “patriarchy” or “rape culture” thing). Less importantly, I’d get nervous asking someone out regardless of whether or not I was into them. Practicing on a statue would make me nervous.

“Go out with female friends to attract available women via jealousy.” – Admittedly, this is one of the ones I got from the Playboy Adviser about a decade or so ago. The theory was that women tended to look twice at any man on a date, even if he wasn’t terribly attractive. While I suppose one could expect some sort of advice based on sexism from Playboy, the fact remained that if I had any female friends who I was close enough to go out on the town with, I’d probably want to date them, not use them as “bait”. Besides, that’s still using someone else for my benefit, isn’t it?

“Just live your life, go about your hobbies, and things will happen.” – Honestly, this was the one that I subscribed to for the longest time. Variations on it include, naturally, only asking out people who are into the same hobbies or social clubs you’re in. It may be solid advice if one, say, is an avid exercise junkie or goes to a gym, or into dancing, or so on. Unfortunately, my hobbies are mostly isolated ones which do not promote opportunities to date or cultivate social situations. My hobbies are basically reading comic books, watching anime/cartoons, or attending comic book movies. Comic book shops are not the place to go trolling for dates, and neither are comic book message boards or tumblrs. At worst, you’ll be seen as some gross creep for doing so and scaring off the women who are there just satisfying their hobby. But most likely you’ll be searching for people who aren’t there, because most of those circles are run by men who get very clannish about that sort of thing. Nobody ever earned a date by going, “Hey, I actually know the origin of Rocket Racco0n! Want to discuss it over tea?” In the end, female comic book fans are still people, not some alternate class of beings. They still have the same wants and needs that any other person has, and that includes looking for traits in lovers that I don’t satisfy on any real or theoretical level. I’ve spent years just living my life, cultivating my hobby, hanging out with friends, and absolutely none of that ever led to a romantic encounter with a female friend or a stranger. I’m not about to start trolling FORBIDDEN PLANET looking for a date now.

“Date online.” – The ultimate format to be genuine and open, eh? The main reason why I don’t is because anonymity and text on a screen doesn’t erase the hang ups for me. I still never know what to say, even if I have been reading someone’s profile for hours. What is the best opening line? Use a cheesy line from a book, and it’s dismissed as stock and desperate. Use some reference to the profile? Just say “hello” and risk being ignored because you’re one of 14,000 people who start off that way? And no, I am not even entertaining what is perhaps the most common form of internet online wooing: “yo honey can i haz tits pleez?” as sent by someone named “BigPenius2014” or something. I mean, do I have to? That’s just lewd and crude and stupid and terrible regardless of the format. And it’s also why any women who do date online are so burnt out that they won’t bother responding to some neurotic wreck like me who can’t even figure out what to type in an inbox.

“Just pay for it.” – Yes, believe it or not I have gotten advice regarding the use of prostitution more than once; especially when someone admits to being a male virgin over the age of 12 online. This naturally ignores the entire premise that most prostitutes are minors or women who have been threatened, bullied, attacked, and violated by pimps or others in their life, and that the sheer act of sex should outweigh an encounter with a traumatized woman who is not there for anything regarding pleasure. As if the moral reasoning shouldn’t be enough, I am hardly in a financial position to afford such things, even if they were legal. My friends have gone to Las Vegas more than once and I am not sure if they ever employed the services of legal prostitutes there or they merely utilized the drunken frat house lifestyle there to land short term lovers, but I never could afford to go with them nor wanted them to pay for my trip. Once I did have to turn down an offered trip to a strip joint for similar reasons; I feel most of the women in such establishments are desperate women being exploited, and I’d also feel like more of a circus freak needing my best friends to pay for such things to me because I am too much of a loser to even afford it myself. Some will mention that since men are expected to pay for dates anyway, prostitution is just “cutting out the middleman”, but I disagree on every fundamental level with such an estimation. There is a difference between paying for a meal or some drinks while getting to know someone or sharing a fun night out versus handing someone a wad of bills to dance for you or worse in a dynamic where if she refuses, she could either lose a job or face a beating. Sometimes I wish I was a real superhero so I could save the women who have to work under such conditions.

“Are you sure you’re not homosexual?” – Maybe not advice, but usually something which I have been asked online more than once. Given the social pressures that exist, being “in the closest” is still a thing for many men and women, even if most of America (at least the east coast in general and NY in particular) is more open about such things now than in 2004 or 1994 or 1984 or so on. There are times I genuinely wish it were that simple, because I interact easily with men and there is much less social anxiety for me. However, I have never been interested in men romantically, nor been tempted or curious. I have nothing against those who are, and in fact have had some homosexual friends dating back to high school (whether male or female). I am not “asexual” either – that would imply a total lack of desire, and it’s not desire I lack. Trust me, I genuinely wish I could switch off something within myself which would cause me to lose any feelings of lust or mournful emotional attraction to women and go about my life without that. During some periods of time I have tried to do so, burying desire and attraction as deep into myself as I could as I lived my life just working, reading comics and hanging with friends on occasion. It has yet to work; it only buries the problem, not solves it.

“Read a book/take a course on how to date.” – That’s just a way to continue this cycle while allowing someone else to profit, isn’t it? No one book or author or source works for everyone, and everyone will recommend something different. Atop that, there are plenty of sleazy authors trying to sell sleazy advice to desperate loser men. Pick-Up Artists – sometimes dubbed PUA’s online – thrive on a healthy market of these sorts of men. I can’t imagine with there being so many variables to human interaction that any set code of rules would work. It doesn’t help that a lot of PUA stuff is usually pretty demeaning to women, and seeks on preying on those who are vulnerable (or under the influence of alcohol). I mean sure, I think most men have fantasies of being able to walk into any bar, be Mr. Cool and walk out with any woman they desire. But that’s sheer charisma or looks, not badgering someone. Advice books or courses authored by women also have another problem – they tend to be advice on what attracts that particular woman. A lady who is attracted to shy bookworms will no doubt advise everyone to hit up their local bookstore and make googly eyes at women in the MYSTERIES section. I am the definition of shy, damaged goods who hides in a corner, and yet no matter how many women have told me in some form that they adore men like that as opposed to jocks or studs, I’ve never once succeeded relying on those details. Besides, most of these things always seem like more of a sell than a chance to help someone. “Yes, you too can woo all those ladies at work or the bar…just for six easy payments of $19.99!” No, thanks.

“Go to bars and clubs, everyone gets laid there!” – That requires more money than I have if prolonged. Besides that point, I am not comfortable in either setting. I don’t enjoy getting drunk, because I dislike losing control over myself and acting like a goofy annoyance due to it. I also don’t enjoy the idea of trying to prey on women who are under the influence. Clubs seem to encourage more drinking and drug use than bars, but above all I cannot dance worth a lick. I have no interest in dancing and have no desire to embarrass myself on the floor. I cannot seamlessly integrate myself into those situations, especially with music too loud to hear, and any attempts to go to bars or clubs either alone or with friends have proven to be wastes of time. I spend the entire night trying to piggy back my friends’ conversations, at best. I am an accessory to their evening, and nothing more. Such settings rely on not only an audience under the influence, but on the allure of charisma and physical looks alone. Had I the sort of charisma and physical looks to succeed in bars or clubs, I would not be the Dateless Man. Instead, I have something which appears to be the very opposite of charisma. Any man placed beside me becomes more attractive and desirable to women based on sheer comparison. Even if I wanted to have aimless hook ups, I lack the sheer chemistry to do so. I am no woman’s fantasy. I’m certainly not a woman’s nightmare, if only because sometimes fear can be attractive to some people. I’m more like every woman’s tedium, the physical manifestation of waiting on line at the DMV. I am the angel of boredom. A better time can be had with anyone, anywhere else. And that’s what people want, a good time.

That’s about all I can think of in terms of the best of the lot when it comes to dating advice I have gotten. If there was some fool proof alchemy to it, we’d all know it because it’d have been commercially sold to us by now. At this point in my life I am not looking for advice or even success anymore, because I have given up on both. At this point I want to understand, for pure intellectual curiosity. Why have I failed, and how? All the advice in the world seems to bring me no closer to that answer.

Rolling as the third wheel – The High School Adventures, Part 1

After two articles dealing with more general rants, it’s time to once again flash back to one of my previous adventures in dating. A sheltered private elementary school and an overall hellish and traumatizing junior high was now leading into high school, where I was well on my way to being shy, nerdy, neurotic, awkward, and overall undesired. The hormones were naturally in high gear, with attracting the opposite sex once again being on the radar. It was the third time I was changing schools since pre-K, which meant a new commute to get used to as well as a new campus and cast of characters to get to know.

It was not only an awkward time of transition for me, but also likely for society. This was the late 90’s into the start of the new millennium. Bill Clinton was just reelected for a second term and the whole sex scandal thing would soon arise. Cable TV and PC’s which were objects of luxury just five years earlier were becoming more common and even expected of “normal” kids’ families. CD’s were in and audio cassettes were out. VHS was in and Laserdiscs were an overpriced, niche product, but these new digital video discs – DVD”s – were being introduced and would soon be the newest way to watch movies. Cordless phones had given way to cell phones becoming more common, even if beepers were still more widespread. Anime (or “Japanese animation” or “Japanimation”) was still a very new, cultish thing which was just barely starting to be translated with some select franchises put on TV, but with bootleg VHS tapes of the latest “Dragon Ball Z/GT” arc or film still being common. Comic books were also still far more of a niche hobby with the bankruptcy of Marvel Comics, the tanking of “Batman & Robin” in film and the general accesses of the industry that’d peaked and crashed in 1993-1994. Out of the ashes arose WIZARD magazine, which was the only real source for official news and discourse. Even the Internet, which was becoming more a common tool of life, was nowhere near what it would be today, or even five years later.

The high school I attended was considered an “experimental” school, which meant they did things in zanier ways than traditional high schools. They had a differently coded grading system, and they weren’t part of any major system wide athletic league or competition. That meant there were no major sports teams, no cheerleaders, no games to attend, etc. Students also had more control over the classes they picked and their schedule, in a way to prepare them for college. Unfortunately, teenagers are not as mature as college kids so it was easy to self sabotage things for yourself. It was also incredibly easy to skip or cut classes while not facing as severe consequences as teenagers would face by, oh, 2008 (when truancy would become a big reason why social workers might intervene with a family). In addition, my mother’s health began to decline to the point that she became handicapped by the end of the 90’s – which didn’t make our already poverty stricken lifestyle any better.

My best friend from junior high, “Russo”, was attending the same high school as I, but as freshmen our paths began to part. His interests and success with girls were more widespread than I, and there was a clique of kids at our new school who had the same ethnic background as he. I, meanwhile, was still into the same dorky things and didn’t have as big a social network. My attempts to remain friends with him usually wound up playing second, third, or fourth fiddle to his newer friends who would speak in their native tongue at most times. At one point Russo put our new dynamic in very simple and blunt terms [which I will paraphrase]: “You used to be the cool guy I learned from, and now I’m the cool guy and you’re not.” Unintentionally or not, Russo absorbed how to be a “cool” NY American from me at such a fast rate that he’d leapfrogged me considerably due to his own natural charisma. Either he was a great student, or I a great teacher, to have taught skills I myself hadn’t mastered. At any rate, we didn’t end on bad or good terms, our friendship just ended. We weren’t in the same classes, and we stopped hanging out at lunch or after school. I never bore Russo any grudge at all; it’s common for kids to grow up and apart as they go through life, especially from tweens to teens. He was there for me when I needed a best friend at the lowest ebb of my youth, providing me with some sense of fun or joy for an overall horrible year or two. It did, however, begin a theme which would carry over to my new circle of friends that I would make.

Two kids who were minor acquaintances in junior high I wound up becoming more friendly with as we shared some classes, and I also made some connections in the small “Comic Book Club” our school held once a week for a year or so. My clique were on the fringes of what was more common for teenagers there, liking similar things like comics and anime, and bordering on the “goth” black wearing metal fans who would cut themselves or wear leather jackets during the summer. Unfortunately, by this stage due to trauma from junior high (the bullying, the mugging, etc.) as well as laziness (or not being challenged enough), by the time I was 15-16 I was becoming bored with school and attending classes more infrequently. The “experimental” school made it easy, via lax enforcement, to skip classes yet hang out on campus, in the library, or in the cafeteria for most of my time there, and I took advantage of it. I still had awkward gym classes where I was concerned about my weight and where I was always the slowest, lamest guy on court who had to worry about his locker being raided. And there was this huge guy who I shared a few math classes with who threatened extreme bodily harm if I didn’t “help him out” with tests and questions in class, which I always meekly did. But I was struggling with math myself, and school in general rarely interested me. I began spending more time with my friends (who all cut classes sometimes, some more and some less than I) and hanging out on campus more than studying. This drove my mother nuts (as one could imagine), and led to some of our worst arguments we’d ever have.

Now, when “normal” kids would skip classes and just hang out on campus all day, they usually did things that you’d expect of teenagers. Drinking, drugs, sex, and/or other assorted larcenies (as there were some gangs around). I didn’t do any of that. Instead I and most of my clique spent our rebellious truancy period playing paper and pencil role playing games like “Dungeons & Dragons” or various WHITEWOLF games (“Vampire: the Masquerade”, “Werewolf: The Apocalypse” and so on). I even would make my own games aping the basic systems of those, but working in my own themes, tastes, and engines. Instead of working on classes or term papers, I’d be inventing some RPG about heroes fighting demons for a d12 system. These games were crude with ever changing and broken rules, but we had plenty of fun. Yet even within this circle, I never any drugs (weed and acid being the most common) or swigged any liquor that someone had brought over. Hell, I’d never even smoked a cig or wanted to! Any time not gaming was spent just shooting the breeze amid dodging patrols from the school security guards, deans, or other “rentacops” as we called them.

My social circle was growing and a part of me assumed that I’d simply find a girlfriend through proximity like everyone else was. Girls hung around the fringes of our goth circle, there was always the one or two random class I attended, as well as fresh crops of freshmen every semester. Yes, 17 and 18 year olds dating 13-14 year olds was not uncommon at all; so long as everyone was attending the same school it was socially accepted. By this time my sense of humor had long budded into a sarcastic cynicism, and I sometimes was guilty of slinging insults and barbs at my own friends – who always responded in kind; teenagers talk trash, I guess. I also was the guy who’d eat a bug or some trash on a dare; lord, do I regret that stuff now. It was compensation for not being tall, or handsome, or hip; I wanted attention and some sort of rep among my clique for something. My perennial stubble (and occasional bursts of temper) earned me a nickname in relation to a bear, which doesn’t sound as cool as it seems. Yet beyond skipping classes I wasn’t much of a troublemaker, or a dangerous rebel, or a tough guy – even if I always wanted to be. I started dressing in black, wearing a black leather trench coat, and other sort of desperate things. At the very least, I learned that I like wearing black. I also was probably at the most hypocritical stage of my life; it was common for me to make jokes about the age gap between my friend and whatever girl they were dating, despite being older (by months or a year at times) and being into said girl myself.

Unfortunately, a girlfriend by proximity never happened. I never got any vibes from any girls I’d met or hung out with that they ever liked me more as some quirky oddball guy who was their boyfriend’s friend or just an acquaintance or classmate. While I was hanging out with larger circles than in junior high, and we were into many of the same dorky things, there always seemed to be this invisible wall between me and them. They seemed to “get” or “catch on” to certain social graces, body language, and elements with dealing (and being dealt by) the opposite sex that I never did. Much as with Russo, I wound up as the third wheel intruding on someone else’s good time with a girl if I wasn’t careful.

The adventure this long rambling set up is leading to captures this theme perfectly. In fact, it was probably a perfect image of my awkwardness and bad luck with girls as a teenager. At one point when I was about 16-17 and a new semester began, that meant new students either as freshmen or transfers from other schools. One of them was a younger girl (she was about 14) who I will dub “Jackie” (which, as always, was not her real name). I forget exactly how she came to be with our circle but she started hanging out with us and integrating herself into the group. By this time my friends were usually either dating someone or in between one break up and their next relationship; some were always single or always not at varying intervals (aside for me, who was always single). Jackie was energetic and sassy, and overall a lot of fun to hang out with; very much “one of the guys” as it were. Most of my friends were middle class kids, and always one in the cast had some rather open minded parents who didn’t mind a house full of their kid’s friends or an open acknowledgement that house parties happened.

Drinking happened at these parties, but not as often as one would think; parents always noticed missing booze. At any rate, I was desperately trying to figure out some time or line to reveal my feelings to Jackie and ask her out. Perhaps due to my experiences in junior high, with the “She Likes You Game” and with 7th grade, I was deathly afraid of it “getting out” that I liked a girl. I feared some of the same ribbing that I, hypocritically, was usually eager to dish out. I also was always guarded about any vulnerabilities or weaknesses, as they’d always been used against me in the past. Recall, the first girl I ever had a crush on turned out to only pretend to like me back on a dare.

Yet at one house party I was trying to make my move, or some move, or something. Jackie and I happened to be alone in my friend’s bedroom while the rest of the house was occupied with the rest of our friends listening to music, playing video games and/or possibly drinking, I forget. Believe it or not despite being a horny teenager, I actually would talk to girls I fancied about small stuff or whatever was bothering them. I imagined that I’d become their friend first and then, if feelings were mutual (or if they pitied me), a relationship would commence. I was chatting with her about why she was depressed this particular day (as she had a rough home life) and trying to figure out some way to be nice and help her while sorting out how to ask her out. And then she said it.

“I’m depressed because I like your friend M***”.

Here I was crushing on someone and being “that friend” when I was just the third wheel between her and a bud of mine. That naturally put an end to any attempt to ask her out or even entertaining it, forever. She did date that friend briefly; it didn’t last. Years later some of my friends were remembering old times with past friends, and another buddy claimed that Jackie actually said she liked me to him but he never told me. I denied it was true and related my story, and he said, “Oh, she liked all of you. She’d totally have gone out with you if you’d have asked.” I never quite was sure which version was true, but as always, it was loo little, too late, for a perennial third wheel.