Dateless-Man vs. Random Reunions and Related Ramblings

“I’m an old man. My life is really over.” — Al Bundy, “MARRIED…WITH CHILDREN” episode #112 (“If I Could See Me Now”), circa 1991.

With March about 2/3rds over it’s time for another glimpse into the modern world of Dateless-Man. To think when the blog first started in 2014-2015 I sometimes got 2-3 posts within a month — especially if I was feeling low. These days I sometimes struggle to hit once a month. My new job and my work with comic-related articles online often keep me busy. I’ve hit a lull for this start of the week so I figure now may be the last shot at this.

As of this writing, I am nearing my 5th month at the new job. I am still seven away from passing probation, and every week is nerve wracking. It isn’t so much the job itself, which is stressful enough. It’s all the micro-management and nit-picking rules within the agency which are bogging me down. There are so many pratfalls, so many technicalities to cross or opportunities for reprimand. After working a job with fellow oddballs and outcasts for over six years, being surrounded by so many “normal” people also doesn’t help. “Normal” people have no imagination and little empathy; they see trees, not forests, and never really consider the bigger picture. Even planned acts to try to build morale at the lowest employee levels are just focus-grouped programs on a spreadsheet. It didn’t help that I learned via co-worker gossip on an elevator ride home that one of my fellow workers in my section — who had about 2-3 months on me — was randomly and unceremoniously sacked. The anxiety that comes with every commute, every shift, is worse than even the highs and lows of a sales job in a less-than-stable industry. But, hey, it’s a job with decent salary, promotional opportunities and, gasp, benefits with a pension. Therefore, in America, those are the sorts of things that can only be had after a lot of nerve wracking.

Therefore, it was an interesting time for a bit of a high school reunion. Back when I was in high school I was pals with a clique of geeks and freaks, and while I may have been the most stiff of them, we had fun. We cut classes together, played table-top RPG’s (some of which I made), watched anime, went to movies, hung out, etc. About midway thru high school, one among us left for Florida and it’d been about 20 years since he’d been back in New York. Just being old enough that I could literally think, “I haven’t seen a friend in nearly 20 years” is still the sort of thing I can barely get my mind around. I need a nickname now so I will go with “Billy.” He came from a troubled home, often at war with his mother and often dabbling in things from self-mutilation to constant use of drugs like acid. Thankfully, a change of scenery, maturity, and distance from a dysfunctional family mellowed him out. I’d interacted with him extremely rarely online, even after I joined Facebook. That was a switch since back in high school, he was on AIM all the time. It was the week of his birthday and he’d taken the trip with some co-workers of his, and was sharing a Airbnb with them not far away for the week.

Most of my closest male friends were there. M**** from “Rolling as the 3rd Wheel”, and most of my pals from “The Everyone is Doing Better Than You Party”. Due to schedules and whatnot I hadn’t seen most of them in over a year. It’s said that men are often more prone to leading more solitary lives once college ends and careers begin, and that’s been mostly true. The fact that people move is one factor; only M**** is within walking distance anymore, and that adds to the scheduling factor. The other is they can’t plan a gathering worth crap. Whenever we’d rally the gang for a movie I was always the one who had to plan it. Despite over a week’s notice, they waited until the day-of and after work to finally tell me when a gathering was happening, and where.

Naturally this is all happening around when my birthday was. The period from October to March used to be my loneliest time of the year but these days it barely registers. The routine of my workweeks helps eliminate it, and the other is that I am less depressed about myself than I was even in 2015 or 2016. I mentally prepare myself for reaching yet another year older months before. And I don’t make a big deal about it. However, an evening out with pals with a couple of beers and some nostalgic mingling was timed for it. And without it being an overwhelming bar experience with dozens of people, it was possible to actually be heard and not feel as left out.

It was a Latin themed food-serving bar in a hipster area of the city. Naturally this was midweek so it was fairly empty. I was the second-to-last to arrive out of the group, and a few of them had been drinking for at least an hour. It was great seeing Billy again, even if he was quite hammered by the time I got there. He was grateful to all of us for making his teen years more bearable, and the drunker he got, the more earnestly he thanked us. I was reminded of how much more my pals drink than I do, even though it is much less than they were younger. I nursed two beers all night, while the rest easily racked up over $300 worth of booze among five people and two bars. Billy had been closer to some of my other pals than me, but he (repeatedly) mentioned how I got him into anime, and having run those table top games, displayed a lot of storytelling imagination. In addition to talking about old times, we updated each other and talked about life, and general joking around. I was reminded that so long as bar crowds are not overwhelming and music is not blasting, I actually converse quite well.

We were not the only people there, nor the only group celebrating a birthday. There were about five young women in their mid 20’s doing the same at the table just to my right. One of them was wearing novelty “Easter bunny” sunglasses at times. Naturally, telling the staff that it was someone’s birthday and naturally slipping a twenty led to a an off-key crooning rendition of “Happy Birthday” with a serving of vanilla ice cream. By the time the night was over, the bar staff had to sing it about 4-5 times within the span of about 2-3 hours (including for Billy). By about the 3rd time I happened to catch a glimpse of one of the waitresses who just had an utterly priceless “Oh god I am so done kill me now” face in the middle of her joining the obligatory sing-a-long.

It felt good to have a “better” job at this gathering. Being surrounded by my pals who were all continuing with careers and who were all either married or engaged, it felt good to not be the obvious loser of the group. Unfortunately, my pal M**** was currently unemployed, and dealing with that occasionally put thing in perspective. I’ve been there, I know what a slog it is both financially and spiritually. Yet by the end of the night, as the bar had mostly cleared out around 9-ish and some of us (not me) were about to head home, one of my other pals dropped something interesting, and blog-relevant!

He casually mentioned that, “I was going to try to hook up you or M**** with one of those girls to the side,” but apparently they’d had eyes at two of the others in our group who were already taken. I was floored not just by the casualness of it, but by how utterly unfocused and uncoordinated he was about it. He claimed that two of the women were single within that group. He never thought to pull me aside or notify me, or try to coordinate any sort of “wing-man” plan. What kind of technique did he even have? I have never seen him try to “hook” me or anyone up with any woman. One time, over a decade ago during college, he and my other pal “T” once met with me on the street on a random day to claim they knew of a woman from one of their colleges who was single and they were going to “set me up” with her. Literally nothing came of it; not a word, not a gathering, not a name, not a detail, absolutely nothing. It probably was for the best, however. I don’t need witnesses to my failure, and as difficult as it would be to try to ask out a stranger at a bar alone, it would be nigh impossible to do with my friends within ear and eye shot. It would become the defining memory of our lives. I’d have to hear about it forever. No, thanks.

It isn’t that I think some of my pals like to jerk me around concerning my eternal singlehood. There was one time most of them mocked by virginity online, but that was an anomaly. I doubt these hapless half measures are deliberate. I just think they’re pretty bad at it. Working a social grapevine among strangers or even associates to casually introduce someone to a single party and try to talk them up and schmooze a date without it seeming weird or desperate, or a prank, is not an easy skill. Plus, if it doesn’t work out, there could be guilt about getting a pal mixed up with it. And I think they’re just bad at it. While my pride would feel pretty worthless with having to be handed a girlfriend by a friend almost out of pity, it isn’t like I had anything else going on. Plenty of people meet lovers through friends or associates. I never did, and I always saw it as a failing within myself. I was just so much of a loser that nobody ever crushed on me. But maybe it wasn’t quite so complicated. Maybe it was just all luck and being just slightly less able to capitalize on rare opportunities than my pals were. Maybe instead of internalizing all of that and making it personal, I should have just chalked it up to a fluke and kept plugging away. I think one of the other milestones of being in your 30’s, besides being able to say things like “I haven’t seen you in 20 years,” is finally being skilled enough at social skills to want a do-over of high school, because this time I’d kill it. But unfortunately I’m not Benjamin Button.

The unintended side effect of a night which waxed a lot about the shared youth of a group of pals, and one of them thanking the rest, is it reinforced the idea that my best years were behind me. High school felt like an awkward fueled hormone slog at the time, but looking back, were those the best years of my life? Was that peak Dateless-Man? Nowadays I have more maturity and slightly more money, sure, but I have a lot less free time nor that bold, ignorant spirit or youthful hope that I had even at my lowest ebbs of teenage depression. I’ve been there and done that. I know my problems won’t be cured by age. I know “growing up” isn’t some magical rite of passage, it’s just the passing of time.

On the positive side, hanging out with pals like a normal person now and then is fun. And it felt good to have made such a positive effect on a pal of mine at his most vulnerable. The sharing of drunken feelings was at times awkward, but usually alcohol is the only time men are “allowed” to feel things, especially about other men, without it being “weird”. My whole life in ways I felt I didn’t matter and life passed me by, so I would do things to try to matter. Among them are, well, typing wordy crap online. But it felt good to have made a tangible thing for a buddy, even without realizing it.

So in the end it was a fun, humbling, slightly awkward night out with pals which ended in me not getting laid. Some things never change! I hardly expected that, though, and it was a rare night with close friends, especially one I hadn’t seen in “about a minute” like the kids today say. My friends trying to wing-man for me would have just made it more awkward. I went home late on a work-night because I didn’t want to leave, which says a lot. And unfortunately not long after, I learned the latest management company in my building (the 3rd within 10 years) wants to illegally evict my mother and I to jack up the rent, so I may quickly have more to worry about than a job and/or being a virgin. Again.

But for the moment this was an interesting experience that was worth sharing. As well as the proclamation of another year where the period ending in March was no longer my “loneliest time.”


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