If I like paying for dates with women so much, why don't I ask one out?

Or; "Diptych, Panel II: The Beam in Mine."

The first installment of this piece can be found here.

A little while ago, I suggested it’s pretty strange to bring women out to experiences you know you will not enjoy.

More recently, I spoke to a different guy with — to my ears — an even stranger complaint. His big issue was, again, the entitlement. Did you know there are women who will put on their profile that they don’t have time for 50-50 men, who just outright say they expect you to shell out for them? If you think that’s bad, wait until you hear how they acted on the date!

You see why I’m confused.

fig. 1 — The researcher in the field.

The first thing I do when I hear a woman voice expectations I find crass is generally not to approach them, convince them to give a date with me a shot, and then plan to meet at an expensive restaurant. I definitely haven’t done that so often that I’ve become world-weary about the type of women I have to put up with.

Like… why don’t you just not date people you don’t like?

Toward a Scientific Dialectic of Online Dating

I enjoy gossip, and puzzles. I like to spend a bunch of time poking around other peoples’ experiences trying to figure out what’s going on. Whenever I heard complaints like these, I ask a bunch of follow-up questions.

I’ve found that, usually, when I ask why they set up this date, I get a “yeah, I know, I know.” In that case, the mystery is solved — got it, thinking with your dick, understood.

But if I say something along the lines of, “Well, it sounds like you’re dating the wrong people,” or if I respond to complaints about how hard it is to be broadly appealing on the apps with, “Well, maybe it’s a good thing to filter out women with whack expectations,” I get a much more interesting response: confusion.

Put a pin in that.

I’ve observed that a lot of the online dating app discourse is cyclical. By this I mean, if you listen long enough to the complaints of men and women about online dating (OLD), you’ll start to see that people aren’t just talking past each other, but are in fact incentivizing the very behaviors they complain about.

The most basic example of this is pickiness vs. performativity. If we go by the popular discourse,¹ women are inundated with matches and messages, many of which they’d rather not get. As women get frustrated picking through this avalanche, men get frustrated as they struggle to stand out.

If this is the case, then the rational responses are obvious. Women are going to want to get better signs of quality. Ideally, she would like a sure bet the guy lives up to her standards of relationship-suitable; failing that, she’ll settle for burning some percentage of the chaff. Men, facing heavy competition, will rationally seek to maximize their odds by casting a wide net; a more sophisticated actors will seek to understand the standards applied to him and adopt behaviors and affects likely to pass muster.²

With our God’s-eye-view, of course, we see the tragedy before it arrives. Men start swiping right on literally everyone and catch wise to the filters they’re trying to get past, women face a worsened supply glut and lower-quality information and so narrow filters, rinse and repeat.

fig. 2 — The Primary OLD Cycle is so-named due to its popularity in online dating discourse, as well as for the way it usefully typifies multiple observed dynamics.

This basic template keeps coming back to me.

One day, I was hearing women complain about guys who come in hot, acting more interested than they apparently are, given that they seem to lose interest quickly.

The next day, a male acquaintance was complaining about how over-the-top he felt he had to be in messages just to get his foot in the door. After all, no one wants a guy who isn’t sure he’s interested.

If we step back, we can see the broader systemic output of this. If the purpose of a system is what it does, online dating is a machine built to stop human connection.

People who have been emotionally burned become more guarded, learning the danger of vulnerable honesty. People pursuing the guarded feel the pressure to keep their interest, and learn to fear vulnerable honesty. When the pairing inevitably falters, any vulnerability or honesty that did develop is punished — and the lesson that you should be slow to trust, and try harder to appeal, is reiterated. The net effect is that everyone is incentivized to act in precisely those ways which will make it impossible for them to form a satisfying relationship. This self-reinforcing cycle of disappointment and heartbreak, and a lack of awareness of the overall dynamic, a focus on the misbehavior of the other gender, engenders resentment in everyone toward everyone else.

These cycles considered, we can see that what’s happening isn’t that these guys are being irrational — in fact, they might be too rational.³ We can see why this kind of guy finds me just as bizarre as I find them when I suggest they should date fewer women, or try to turn more of them off!

They look at me like, well, what’s the alternative to taking all these women out? Waiting for the right one to come along and find you?

Well… yeah, I guess. That’s what I’ve been doing.

That’s not weird, right?

Physician, Date Thyself

As of time of writing, I’ve been single for two years.

That actually understates how uncommon dating is for me. The last time I asked out a woman was just under a decade ago.⁴

What’s really happening is that I don’t understand the issues they’re faced with because I’m playing a different game:

It’s not that I’m always single. But all my relationships, bar one, have been with women I’ve known for a while. Things just sort of happened, or she made the first move. I’ve never been on a date with anyone I’ve met online. Because of this, if I am on a date, it is with someone who 1. I know quite well, 2. is attracted to anxious autists, and 3. has probably asked me out.

As it turns out, this acts as a pretty strong filter against women who have traditional expectations of gender norms, and for nerdy, willful feminists.

Sure — I can talk up the strategic benefits of my approach (or, uh, lack thereof). There are upsides! They’re just not why I ended up this way; the truth is obviously that I just have a different issue with dating as a man, rooted in an extreme aversion to creating discomfort for others.

I don’t think my backstory is particularly complicated. I’ve always been what one might call a sensitive young man.⁵ I was an over-the-top hopeless romantic seemingly from birth, definitely long before elementary school. As I grew into a middle schooler, I found myself distressed by my inability to grok social norms, not helped by my then-suspected, since-diagnosed Asperger’s. I was fearful of other kids, mostly without a lot of reason — just alienated. I was picked on, now and then, e.g. asked out as a joke once (which I pieced together was the case over the weekend, and had confirmed on Monday). Well, and there was also the second time that happened, though that time, I didn’t fall for it. I got it in my head that I couldn’t trust my read of other people’s intentions, and I got wary about putting myself in situations in which that would lead to me getting hurt. I started to find it pretty unlikely that I was desirable.

As I got older, and more invested in gender discourse, I don’t think it’s super surprising that I found it very reasonable that women would feel put off by men who approached them, and that I felt a powerful need to avoid being that guy. It’s a pretty straight forward case of low self-esteem and a resulting urge to people please.

The Resentment in Fear?

That’s not wholly honest though, is it?

I mean, for one thing, it’s not like we can pretend this is somehow virtuous just because I’m not complaining about women. It’s not like the people pleasing behavior I adopted was attractive, or right.

And for another thing, boy did I complain! I remember a real resentment over the fact that, as a boy, I was saddled with “unfair” expectations, particularly around initiation.

But I think there’s a deeper issue with chalking up current behaviors to childhood fears. I’m not currently avoiding asking out women because I’m afraid they’ll say no. In fact, I’m pretty sure of some who wouldn’t! The reason I find myself recoiling is because I imagine what will happen after — that I will disappoint her by being disappointing, and the relationship will slowly die as I become more avoidant for fear of that.

It’s not that I’m afraid of rejection — it’s that I assume it. That’s what I was really mad about as a kid. Why do I have to be the screw-up?

Why do I have to be all of these things that I wouldn’t want, either? Emotionally fragile, socially shut-in, in equal parts sexually perverse and timid — and worst of all, self-loathing.

That self-loathing has fed avoidance, which has led to a failure to express my needs and desires, which has led to dysfunction in my relationships, which resets the cycle.

Those Who Don’t, Blog

So — yeah. If the men I’m running into suffer from resentment, I suffer from fear. These are not as different as they might seem — both are failures caused by a reaction against the burdens of masculine responsibility in romance. I can tell myself that my reaction is more empathetic, but at the end of the day, women are not thrilled with any of us.

Is it better to avoid responsibility altogether than to take it on and complain? I don’t want to go too far — it’s definitely still the case that these guys are creating problems for themselves, and cultivating mindsets that will hurt them. But I can’t help but wonder if they might be closer to virtue, given they are actually moving forward.

1. As it happens, I’m not totally sold on the idea that the discourse has this right. I think it’s undoubtedly the case in broad respects, but I also think in trying to make categorical statements about gender, we flatten experiences out in a way that’s unhelpful.

2. It’s really not that hard to look up what makes a good profile if you can’t figure it out.

3. well ok let’s not go overboard. I’m just saying they’re being dumbasses but like, I get it

4. And this is only if you count my finally making a move on a friend who had been heroically trying to get her interest through my thick skull over drinks for months as “initiating.” You shouldn’t, obviously, but this is already embarrassing enough.

5. NO WAIT NOT LIKE THAT I CAN EXPLAIN