Dating in an Existential Crisis

Snoopy asking the big questions

I find myself single again in 2021. I was going to wait before going back into the dating pool, but a friend said I might find someone interesting if I dived right in during my existential crisis. That sounded intriguing, so I’m back out there, cell phone apps at the ready.

It’s one thing to think about the meaning of life and suffering endlessly, and quite another to think about dating in such broad terms. Fortunately, this is one part of my life that doesn’t need that much examination. Dating for me is basically two parts: what do I want in a person, and what do I want in a relationship?

What I Want in a Person

All I’m looking for in a partner is someone who I can have interesting conversations with, and who I think is pretty. That’s it. I once had a list that was a mile long: must have similar politics, must be a gamer, etc. But I found that I liked people who didn’t meet any of those requirements, which made me realize that I didn’t understand what I wanted.

I thought I wanted someone who was “compatible” with me, as in they shared all my same opinions and interests. What I really want though is someone to learn from, who can challenge my own thinking and help me understand the world better.

That’s what was so wonderful about my ex. We had very different views, and talking to her helped slaughter all of the sacred cows I worshipped without thinking about them. It was also just fun learning about Jeffree Star’s bullshit and watching Drake and Josh. Those are experiences I wouldn’t have if my partner was exactly like me. 

The other thing I look for is a pretty face. I’ve been called shallow because of this, and I accept that judgment. But the fact is that I enjoy talking to people, and since I have to look at people to talk to them, I’d prefer looking at a face I find attractive. I find all types of faces attractive, and I don’t really have a set of criteria for attractiveness other than thinking, “She’s pretty.”

What Do I Want From a Relationship?

This is where things get a little murky and existential. I wrote a post a few years ago about how awesome divorce is eventually. It was meant to be a joke, but I’m quite serious when I say that my relationship with my ex-wife and son are both much better since the divorce. Which got me thinking: why did I get married in the first place? Why didn’t I ever seriously consider this kind of arrangement when we found out we were having a baby?

Orthodoxy and expectations, both internal and external, are the answers. I’ve replicated that orthodoxy in almost every relationship I’ve been in, but it’s not making any sense to me anymore. I could get into the weeds on that, but suffice to say that if I’m happier being divorced, then maybe I shouldn’t be rushing to get married again. Maybe I don’t even need the “boyfriend/girlfriend” label.

What I know that I want is a pretty girl I enjoy talking to, that I can smoke weed with, and have sex with. Everything beyond that is negotiable, and I don’t know if that needs to have a name or not.

Either way, we’ll see. I’ve had one match on Tinder so far, so it’s still early days. There’ll definitely (hopefully?) be a follow up.

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