Getting back into the dating game

My therapist tells me dating is a lot like job hunting. You’ll never get the position you want without trying. You go on interviews, you scour the web for openings and send your resume everywhere.

An old college friend, who loves basketball, told me you miss 100 percent of the shots you don’t take.

Point is, you have to put yourself out there and actually try.

I’ve been out of the dating game for a while. And even when I was in, I wasn’t that much of a player.  I had encounters and hookups, but no actual long-term relationships. I was also never the one to break it off.

In other words, I was the perpetual dumpee, never the dumper.

For awhile, I was jaded. Then I decided to put relationships off. Save it for later when I had more time. I prioritized other things, and to a certain extent, it’s been good for me. I have a good job, I’ve improved my writing and I’m in better physical shape.

But then I got a reminder that the world doesn’t take a break, even when you do.

A good friend, one I’ve known since I was a kid, got married last year. Like me, he’s in his twenties. When he decided to tie the knot at age 23, I didn’t feel that concerned. He’d been dating the same girl since high school and it felt like the natural progression of their relationship. I felt a little weird since he was so young, but it made sense for them. He also bought a house a few months ago, bucking every negative stereotype about millennials I’ve ever heard.

Last week, I learned he was going to be a father. The baby is expected in spring 2018.

I know I shouldn’t compare myself to others (as my therapist tells me) but all the same it feels like I’m being left behind. I’m not saying I want a spouse or a family or right now, as I know that’s nuts.

Life’s not a race. But all the same, I can’t help but feel like a grade-A loser as compared to my friend who is married, who owns a house, and is an expectant father. While he’s actually being an adult I’m living in my parent’s basement, I’m not moving out anytime soon, I’m up to my eyeballs in student debt and I have no relationship prospects.

And it’s not just him.

Dozens of my college and high school friends (straight and LGBTQ) are getting married, buying homes, or settling down while I can’t help but feel my wheels spinning.

What is this? I mean, we’re all millennials for god’s sake. We’re supposed to be the boomerang generation. And I’m by no means the worst. I know other people my age who have no real job, school or relationship prospects, not that I get pleasure in other people’s failure, mind you.

My therapist tells me this is a phase. That half of these people will get divorced in a few years and I shouldn’t feel bad at all.

But she also told me I should start dating, if that’s what I really need to feel fulfilled. And to be honest, I feel like there is something missing in my life, something that can only be filled by someone.

Gay dating has always been a mystery to me. Maybe it’s because I went to a small, Catholic high school and a small, liberal arts college, and there simply weren’t a lot of gay couples at either. The dating pool was shallow at both schools making it hard to truly get my feet wet.

Granted, it wasn’t a completely celibate experience for me thanks to the bottled up, repressed, Catholic-guilt induced homo-eroticism both institutions helped produce, but I didn’t have any serious relationships, either.

It’s time for a change. I’m putting myself on the market.

Needless to say, this is going to be difficult given my current living arrangements. My parents, especially my mom, ask thinly-veiled questions about dating all the time. “Did you meet anyone while you were out?” or “Were there any girls at the party?” etc. etc.

Dating in the closet won’t be easy, but it’s a risk I am willing to take.

So, in short, I’m giving it a shot. Wish me luck.

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