Why I don't date

A healhty sense of failing at life

Three phontes, with ads for watches on Instragram displayed on their screens

The last date I was on was over a year and a half ago. Two years? I don’t remember. The last girlfriend I had faded out of my life without a clear goodbye, and then after that there were some dates with a couple other women I met, but the concept of dating itself faded as well. I don’t know which ended first, the dating or the desire to date.

Is it just age and the absence of the uncontrollable passions of youth? Is it healthy emotional maturity of not needing to have a human security blanket to smother the bottomless loneliness I used to feel?

When I was in my twenties and thirties, I felt loneliness viscerally. I would be unable to sleep at night, feeling the existential angst of what it might mean to never meet anyone again. I would feel shame and anger at my inability to solve the problem. I could barely focus on anything else in life.

Now I look back on that and it seems like another person. I barely think about being with someone. Specifically I mean a romantic partner. I have more friends now, and an ability to have friends because of so much less noise in my brain devoted to worrying about my relationships with women.

So it all seems kind of a good thing maybe. Without the fear that permanent loneliness awaits me just over the cliffs on all sides of me, I create more, I enjoy my time more, I’m more able to commit to the things I would like to accomplish.

It feels more healthy and balanced to not be chained to the dragon of constant desire anymore.

But, also, I don’t want to die alone either.

I’d be lying if I tried to claim that the only reason I haven’t been on a date in a long time is because something inside me has just mellowed out to the point that I just haven’t really pursued dating. That’s part of it, I literally go days without even really thinking about being with a woman, and during that time I don’t really care about it.

And then sometimes I’ll be out and about and I’ll see a beautiful woman, and I’ll think about how she would not want to be with someone who is basically failing at life as hard as I am.

I mean, I’m almost fifty, half the women who catch my interest are probably young enough to be my daughter, so some people, including the woman I’m looking at, would probably think I’m some kind of monster for even looking at her. But even if she’s within whoever’s judgmental standpoint about acceptable age ranges, I mean, I can’t believe I tick any boxes for what she’s looking for.

After a life time of serial ambitious projects that have all flamed out into nothingness, I still live basically the same life as someone just out of college. I have my shitty small apartment, uncertainties about where my income will come from about eight months from now, and all my plans for where to go from now would be cool if I were under thirty, but at fifty, it seems like it’s just the sad delusions of someone who doesn’t see that they’re past the due-by date.

I’ve always felt inadequate, though, so that’s not something that came with age, just exacerbated by it. I’ve never been a super good looking guy that can appeal to a woman on looks alone. I’ve never had money. In spite of a healthy ego that thinks I’m inherently awesome, I also recognize that everyone else is unlikely to agree based on outward indicators. I feel like there’s only two things that have helped me get into the lives and beds of the women I’ve been privileged to know that way. One is that I’m good enough at talking that I pretty much get them confused enough to think I’m interesting for a while.

The other thing is just persistence, more accurately described as an unhealthy inability to let go. It sounds bad, and it is, but it’s also been a source of my dating success. Essentially, my fear of being alone was so great that it overwhelmed my fear of being rejected. I’ve been fortunate enough to date many women I think everyone would agree are out of my league because I persisted in badgering them into being with me, driven by the fear of the gaping void underneath me if I didn’t.

Which you can easily see would have a pretty obvious downside. I stayed in relationships that should have ended much earlier, I went after women I was clearly incompatible with, I mistook sex for validation. I still conflate sex and validation, so maybe that’s a whole other thing.

But, I can’t deny that unhealthy drive had the upside of getting me out there, getting into the game. That’s gone now… because I’m healthier?

I don’t know how it is for other men or women, even if I have my suspicions, but I’m going to avoid possibly tired stereotypes… anyway, I don’t know how it is for other people, but if I don’t make the effort to cross the street and go say hi to some woman I see, then nothing is going to happen for me.

It’s not like I don’t know how to do it. I’ve got three decades of dating experience, I know how to manage the process of dating. I think I’m actually pretty good at it. I’m definitely better at it, than, say, a dude who has been married for twenty years and is recently divorced and has to learn what the current deal is after being out of the game for so long. I’m definitely better at it than a guy in his early twenties who thinks he knows everything the way that people do before they hit life’s actual problems.

But being good at dating feels like the wrong skill to have. What I’m bad at is life. And no matter how smooth I am in creating light flirty conversation, I can’t make it work if underneath I don’t think I deserve to be talking to anyone. I can’t sell me if I wouldn’t buy me, knowing what I know about me.

My life is not at all like I ever imagined or hoped it would be. I have built nothing that I aspired to build. I’m not at all who I would like to be. At least in measurable terms that I feel adds value to anyone else.

But on the inside, there’s no void anymore. So that’s nice.