“Being Single & Middle-Aged Is like a High School Popularity Contest, Only Now, Every Participant Is Fucked”

Originally published March 8, 2015


  • “I don’t have a lot of friends…”
  • “I got un-vited”
  • “I’ve failed on every level of life”
  • “Y’know, when I was in my twenties? I’d see a pretty girl and I’d say to myself ‘boy, I wonder what it’d be like to fuck her’. Now? Well, I say ‘I wonder if she’d be nice to me’”
  • “I have, like, two friends, and a thousand acquaintances”
  • “I’ve been doing ‘OK Stupid’. How’s it going? Oh, it sucks”
  • “S’pose I’ll just die alone and let them find the body eventually”
  • “Well, I have my cat/dog, and I see my kid almost every weekend, so I’ve got a pretty busy life

I’m of the countless who’ve reached middle-age (let’s call it 40 to 60), with no real idea as to how to form a lasting bond with someone I truly love, or for that matter, just barely like. Furthermore, the process of making and keeping friends is indeed a fuckin’ bitch to deal with. It’s not for lack of trying or intent, mind you, cuz I’ve done the leg-work; I was just never able to figure that part of life out, right from my immediate departure from the womb to this very day.

From my vantage point here in the cheap seats, if you’re divorced, because you were once ensconced within an “at-least-sometimes-happy-family-unit”, you’re doubly-fucked (note title). See, you got a taste of what that kind of life is like, or could be, and sadly, you may never attain that dream.

So here you stand, as fucking confounded as if your current state were a pop-quiz in your worst middle-school subject. One thing you’re to be certain of though, is that while you were married, the dating game mutated into something barely navigable and wholly mystifying (unless you never stopped dating WHILE being married, but who the Christ am I to judge? have at it polyamorists; maybe you know something that the rest of us don’t).

On-line dating? Sure! Why the shit not? You (I’m talking to you, girls, but fellas, I’m not gonna judge) may have even “passed” (read: swiped left) on MY carefully thought out, if slightly verbose, profile. As many of you know, it sometimes might even work out. “Yay you!” if that’s the case; stop reading right here and go give yer special person a hug and a nuzzle. Oft-times, though, it runs the shit-trail from a sad waste of time and money, right up to a crushed opinion-of-self-worth at worst.

Me? If you don’t know me well, I’m a life-long self-sabotager, always looking for an opportunity to throw a monkey wrench into an already twisted situation. It’s referred to in my family as “pulling a Sargent”, but that’s an entirely different opus (remind me sometime to tell you the story about “the slingshot, the pant-less grandfather, and the sunflower garden).

Date-wise, in my case, there’s always gonna be the point when my new “contestant” prods and pries about my past and whatnot, asking in ten different ways “what makes you tick?”. My honesty, in these cases, probably shouldn’t be as colorful as I tend to make it (that specific color being “none-more-black”), but I’m too old to go changing at this juncture.

I recall one occasion when, three-quarters of the way through our meal, I thought to myself “I guess I like her enough to see her again; I mean, I sorta like her. A little, kinda. And I don’t want to be rude in not asking her out for another date” (misguided manners/people-pleasing being an entirely different entry). Upon asking for a second date, my companion replies, mid-chew no less, “uh-uh, I don’t think so. You’re too dark and disturbed for me”. Oh. OK, I get it. I asked for that; but in my flimsy defense, she’s the one who was mining the skeletons with a snow shovel; I guess I just hucked too many bones at her.

Another time, my verbal truths were trumped by my date’s actions. About a year-and-a-half ago, I met up with a woman who showed up as plowed as I’d ever been back in the day. If I didn’t know better, I’d have sworn she had Parkinson’s, she was shaking so badly. Mid-way through our respective beverages (why bother with food three days into a six day bender?) she coyly let her blouse slip down around her shoulder, upon which I could see what looked like a jailhouse tattoo denoting a day, month and year in barbed wire script.

“So”, I asked, “what’s the tat mean?”

“That? Oh, that’s the birthdate of the baby I gave up for adoption. See, I didn’t really know the father. Actually, I met him on OKCupid, and only saw him that one time”.

Once? Silly me. C’est la vie.

Despite the problems that go along with honesty for the sake of an interesting conversation, I’m wondering if we were all truly forthcoming in our initial profiles, by letting our freak flags fly high (we all gots ‘em, yo), that there may very well be many more suitable matches made from the gate on out.

It’s gotta be worth a shot, right? Me first. Here goes nuthin’:

46 yo divorced male, balding, 6 foot (previously 6’1”, but probably shrinking due to a calcium deficiency), “possessor of” bipolar disorder II, recovering alcoholic, possible ADHD, passive aggressive egomaniac with an inferiority complex, with no interest in sports OR participating in gatherings of three or more, seeks same/compatible female, any height, baggage accepted. Turn-on’s include “Coke Blak” (Google it…), “The Walking Dead”, “The Monkees”; turn-off’s: litter and mean people. Strict vegetarian, non-smoking, ultra-right-wing conservative, in-door rock-climbing meditating yogis need not apply.

Ya got that girls? Good. I iron, and I enjoy doing laundry, too.

To my “sorta-kinda” shame (shit, why stop being honest now?), I’ll admit that I’ve even reached out on Facebook for interesting friends & companions (FB’s an “emotional vending machine”, right?), I’ve gone out with active drunks and sober alkies alike (NOTE: in many cases this is like two dump-trucks crashing into each other, however, I will cop to the fact that I’m usually the one running on high-test, full-speed ahead during that particular game of chicken).

What have I learned? Well, life overall is not easy for any of us. How many of us suffer from a low-level depression, a nagging ennui that periodically grabs at your gut with the intensity of a near-miss fever dream? I know I do, truth, no lie.

The world, under the best of circumstances is a scary and lonely place, even during the most God-given of beautiful summer days, if that’s your thing. The best I can figure is that we’re all broken and afraid of each other, OR we’ve found our caste and stay swaddled within it, fearful of striving for more, while concurrently wary of dirtying ourselves with those “grimier” than us. If you’re an isolator like myself, its even worse, as the fears, lifelong to be exact, run deep and thick, permeating your bones and blood.

I suspect there are more of us than we know, a (painfully and awkward) silent majority who, although they seem to have it all together on the outside during the daylight hours, bow before the self-perpetuated lies of their scabbed and bruised being, just prior to turning out the bathroom light, with a scintilla of hope to die in their sleep, peacefully and painlessly.Its loneliness; a barely tolerable self-loathing, at a constant simmer, just waiting to boil over. I know for a fact that some of us go to extremes to forget this, going so far as to not to looking at their reflections in the mirror for fear of confronting “reality”, perceived and otherwise.

By the gods’ graces though, I can assure you that there are a select few folks who transcend those routes entirely, who give of themselves in such a way that they go so far as to unknowingly save our seemingly broken lives on a daily basis (I do hope you are a lucky recipient of this gift, as I am). Its quite possible that you yourself are one of these people, although, that’s not for you to decide, but rather, its the job of the recipient of the act.

Trust me: I’m well aware of the fact that I’m not making any more friends heading down the path I’ve chosen for myself, and most certainly, something as benign as online dating isn’t gonna “fix” me; more often than not, I fearfully, with shameful arrogance, spurn the outstretched hand of those who selflessly reach out to me. But, I’m learning to do an about-face, as painful as that can be.

Recently, I asked a married friend of mine, solidly middle-class, concrete middle-management, firmly ensconced in the rest of his life (by choice, more power to him), how his yearly check-up went and he said it went “great, except for the chest pains”.

“Fuckin’ WHAT??!!!!???” I says.

“Yeah, but I think its all of the life-stress”.

Well, sure. “Life-stress”. I understand. But that’s a waking night terror that i don’t wanna live.

Understandably, I may sound bitter, but I’m really not; that’s just my natural default. I will, however, admit to being afraid, to being more scared of you than you are of me. But sometimes, and I believe this to my core, people get through that. Our little worlds would be much better places if we all took the time and responsibility of writing ourselves a love letter every once in a while. We all deserve it. I know I do.

Recently, there was this guy whom I sorta knew in high school, who said that he didn’t have a lot of friends, was getting divorced, and knew not where to begin in “rebuilding the team”. Anyhow, in the closing of his note he said “lets meet up anytime”, that he’d really “enjoy” it.

Honestly, that was one of the nicest sentiments extended to me in a long time, and I thank Christ he had the balls to say it, cuz I’m getting to the point where i sure don’t.

I will, however, keep fucking this game up until I get it right. See you on the court.

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