The Longer I’m Single, The More Undateable I Become

The Longer I’m Single, The More Undateable I Become

I haven’t been in any semblance of a conventional relationship in like eighteen months — I measure this by sober sex — so I guess you could say I’ve been single for a while. It’s been a shock to my system, a glass case of emotion where I’m getting drunker than I ever used to, mood swings like I’m on The Bachelor, more unkempt, more laissez-faire. Essentially the adventures start to build, the weekends a haze, and my penis is more confused than the time at summer camp when all of us tried the Big Red Challenge.

You see, up until a year and a half ago, I’ve always been a “relationship guy.” You know the type. We’re single for all of two weeks at most, because when one relationship crumbles, we always have a top-rated Prospect in the minors, take them out to sushi, and literally charm their pants off on a consistent basis until bingo-bango-bongo, we’re a couple (if you’re afraid of relationships you call this phenomenon “being exclusive” but just call a spade a frickin’ spade: you’re a couple).

And then, about a year and a half ago, I had some sort of epiphany. Like a mini Peter Gabriel was on my shoulder serenading me with Solsbury Hill. I was seeing a girl I liked – immediately after being left by someone I was in love with – and it was fun, we laughed a lot, and we had sober sex, but when we went to have “the relationship talk,” she asked me to commit. Usually, this was a no-brainer; usually, it was me who instigated these talks. But for some reason, I just blurted out “the only commitment I can make right now is to Bill Belichick and the New England Patriots.” I convinced her to continue whatever we were sans label, secured a handful of dates, ended up sleeping with someone else, and then started to juggle these two girls at once. But since I’m like a gorilla and can’t do anything subtly, this crashed and burned.

So why did I not commit when asked? Because she wasn’t The One. My personal belief is that there could be multiple The Ones out there for me, but this just wasn’t one of them. I also want the next girl I truly call my girlfriend to be the last commitment I have to make. I recognize this means I might have to be single for a long time – which is a clear defamation against my track record – so maybe the last eighteen months has been some sort of relationship withdrawal. But as I sit here in the cubes about to begin another long week of being stuck in the spin cycle – work, gym, Trader Joe’s, gamble college basketball, rinse, repeat – I’m starting to think that the longer I go without a girlfriend, the more I become undateable.

Sometimes I wonder if the longer I don’t have a girlfriend, the more I am perceived as damaged goods, like the kale you bought for your New Year’s resolution but have forgotten in the back of the fridge. Is there something wrong with me? Is the consensus that because I’m single, I’m a fuckboy? Sadly, the unused condoms in my nightstand and pizza boxes stacking up in the recycling bin would indicate the opposite.

I’m becoming way more skeptical of everyone new that I meet, which makes me atrocious at first impressions. The older I get, the harder it has become to act like every day is the first day of freshmen orientation. The longer I go without meeting someone perfect for me — and don’t even get me started on how difficult it can be to actually meet real humans — the more pessimistic I become. Snarkier. Angrier. Impatient. And nobody wants to date that guy. It’s a downward spiral. The first impressions I used to give off was that of the sweet helpless romantic boy next door. Now I’m literally The Improper Brostonian, raising my voice to obnoxious decibels to say douchey things in a semi-real Boston accent, and it’s all because I haven’t been committed to any one girl for a while. And yet here I am, refusing to commit to anyone who I couldn’t see having my children.

This past weekend I was, of course, acting like the moron I’ve become. I was sitting at the bar, making out with some chick I’d been chatting with for maybe fifteen minutes when I put an end to it immediately. I could have easily brought this girl home, which is really saying something for me because normally I strike out at rates that rival Chris Davis. (It’s hard walking into bars and seeing every bangable chick surrounded by Seal Team 6, these like 6’4″ Miami Dolphins linebackers and I’m trying to squeeze in between them like, “Hi, look at me. I might be short but I’ll keep you laughing until you’re dead.”).

So why didn’t I try and schtup? Because your boy, the idiot that I am, had already texted my organization’s highest-rated Prospect to have her meet me at the bar, and she confirmed that she was on her way with her roommate. She arrived, we got savagely drunk, I bought her Tasty Burger (shouts to my boy Ziggy for hooking me up with two free milkshakes), and she went back home with her roommate. I started walking home, one hand frozen to the milkshake, the other sending a long and slightly incoherent text message asking her out to sushi, ending my blabbing with a “yes/no/maybe.” (I used to be so smooth, what the hell happened to me?) Unsurprisingly, the rejection came shortly before noon the following day: “I think we’d be better off as friends. I’m so sorry.” (Don’t apologize, babe. I’m not the one that just turned down an awesome sushi meal where I guarantee I’d have you laughing all night.) We’d had a lot of fun hanging out in group settings, so why didn’t I even get a shot? Have my worst fears come true? Am I really undateable?

The Roommate, as always, talked me off the ledge. “She was too quiet for you anyway. You’d be bored after a month.” He was 100% correct, but has being single so long backfired and actually clouded my judgment in who I should pursue? She hit four out of my five required tools – cute, smart, funny, Jewish – all that was missing was the next-level outgoingness required to keep up with me. Has being single really forced me to want to settle for anything less than a five-tool player? And as I said, maybe some of my tools have become dull, too, though at the core of it I’m still the same “relationship guy.” I just need to find a Prospect fearless enough to cut through all my newly grown rough edges and realize that I am still very much dateable.

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Boston Max

Spending my retirement fund at Trader Joe's and trying to remember to check my mailbox semi-regularly

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