Why am I so annoyed when dudes complain about paying on dates?

Or; "Diptych, Panel I: The Mote in His Eye."

The second installment will be linked here when it is published.

Now and then, I realize that I keep to pretty specific social circles. I don’t easily made friends with other men. The weirdos and softies I do ok with, less so the general population. I’ve always chalked this up to a lingering prejudice towards normies, but I’ve realized that it has a lot to do with my troubled relationship to masculinity, I think, so I’ve been trying to broaden my social horizons.

So a while back, I’m bonding over a shared hobby with the kind of guy I would usually avoid. Not bro-y per se. Cocky? Guy-at-pub standard. The kind of guy who has good taste and would be nice to your mother, but could get all “What’s your problem?” if you took looked askance at an off-color joke. Trying to make conversation, I ask how his weekend’s looking, and it turns out he has a date.

As if to affirm my prejudices, he gets right into complaining about how expensive dating is — to his credit, not mad, more “amirite?” bemused, as if sharing a common experience. But at first, I’m genuinely kinda lost — it’s not like there’s an entry fee to hanging out with women? Ah, but there is — he means how expensive women make dating, the accumulating costs of all the takings-out to dinners and drinks and “experiences.” He is, admittedly, a little mad. It’s the entitlement that gets to him.

Crazy tbh, because it’s his entitlement which gets to me.

There’s something uniquely off-putting to me about this sentiment, undignified. Maybe it’s the way I was raised — I tend to like treating people to things, and to be uncomfortable about demanding recompense. Partly this is because my family is full of neurotics, sure, but part of it is genuinely down to values. To behave otherwise seems uncharitable, and to miss out on a simple pleasure of “hosting,” un peu de noblesse oblige.

Reaching for a way to describe my feelings, I want to say unchivalrous — but since when is that my value system? It’s not as if I’ve ever been served well by gendered dating norms.

Why do I get all “What’s your problem?” about this?

What’s His Problem?

In the abstract, I’m sympathetic to the idea that men are judged by unfair standards. I’ve never been able to play the confident leading man, which means whole swathes of women are going to be uninterested in me — and I know what it’s like to angst about that, having been a depressed teenager. But there’s something that feels immutable about being nebbish, something prejudiced about being called gay. He’s just a stingy dick — right?

There is something fundamentally illogical about the guy’s situation. Here’s a guy who goes on first dates quite frequently, by choice, and who is always doing the asking-out, and so the lion’s share of the date planning. He is thus regularly choosing to bring women to restaurants that are too expensive for dinners he does not want to pay for.

That’s weird behavior!

Even if one were to find this standard unfair, it’s hard to sympathize since the costs associated with it are extremely avoidable. Just ask the woman out to coffee, famously a very appropriate first date.

He counters that this is just not how it works. Of course, no one is holding a gun to his head — but his goal is to impress these women, and he’s found the women he dates to have high standards. So, yeah, he could save a ton of money, if he didn’t care about getting a second date.

This makes something click for me, makes the problem anthropological.

Taking his assumptions for the sake of argument, the problem seems to be the women he’s choosing to date — if he resents trying to live up to a certain materialistic standard, he should be working to date fewer women who hold it. I reason that there are two factors which are locking him into the wrong dating pool:

1. Normie taste: To be honest, I keep remembering profiles I’ve seen on Hinge basically laying out an expectation to be pampered, and I prejudicially assume that the general vibe of that kind of woman otherwise appeals to him.

2. He’s on dating apps, rather than approaching women he knows at least well enough to gauge their thinking on this sort of thing — if you’re just swiping on everyone, you’re going to get a lot of weird dates, and fail to avoid bad actors.

So, it’s not all his fault — it’s also the rat race of online dating, which he should just opt out of (so it kinda is all his fault).

The Only Dating Advice I Have to Give

In the moment, I had to tell the guy I just don’t share his experience. In large part, this is just because I don’t really date, not in the way he does.

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. And so, I have found myself surrounded by women abnormally likely to take offense if they think you think they need pampering (or at least, who would like to be perceived as independent).

For such a woman, going Dutch on lunch is a pretty cheap signal. Far from being nickel and dimed, I’ve had to develop a sense for how to tell if someone is serious or not about being interested in paying their way!

As an aside, I think I’ve worked out a fool-proof method for surviving the “Are you sure?” “I insist —” “Are you sure?” “No, really —” thing. The key is, you have to insist on paying for the meal three times.

“Where do his intentions lay? Or does he even have any?”

First, the Offer

“Oh, I’ve got the bill.” “Are you sure? I can pay —”

Don’t make the mistake of taking this as a statement of intent. You have both made an offer — an initial signal of generosity and self-reliance. To ascertain the intent behind that signal, you have to test convictions.

Second, the Offramp:

“Seriously, it’s no problem.” “[relieved] Are you sure? / [determined] No, really.”

Here, you give your opposite the opportunity to gracefully climbdown from their offer, to “let” you “insist” on paying. If they were serious, they will seek to extend the same opportunity to you.

Third, the OK

“Of course, I’m happy to pay. / “Alright, alright, if you’re sure.” “[assured] Thank you.”

Present one of two outcomes for confirmation — either you are going to pay, or you are going to split the bill (if you receive further waffling rather than assent, the safest maneuver is to perform a fait accompli by grabbing the check).

The Fear in Resentment?

Clearly, I have all of this figured out.¹ Why doesn’t he? Just date women with less extravagant taste — or maybe, just take a few weeks off from dating, store up a couple paychecks.

I wonder to myself if a sort of anxiety drives this behavior, a need for companionship which can’t take a break. The Will to Change offers this as an explanation for the seemingly addictive — compulsive, but disdainful — way in which some men engage in casual sex and dating. Quoting Steven Bearman’s “Why Men are So Obsessed with Sex” at length, hooks writes:

“Sex was, and is, presented as the road to real intimacy, complete closeness, as the arena in which it is okay to openly love, to be tender and vulnerable and yet remain safe, to not feel so deeply alone. Sex is the one place sensuality seems to be permissible, where we can be gentle with our own bodies and allow ourselves our overflowing passion…”

Compulsive sexuality, like any addiction, is hard for men to change because it takes the place of the healing that is needed if men are to love their bodies and let that love lead them into greater community with other human bodies, with the bodies of women and children.

This resonated deeply with me — it’s certainly why I have always been fixated on this topic: Sex is mentally conflated with love, being desired, having one’s belonging affirmed. My anxieties about it stem from fears of not being seen, not being valued. I could see how that fear might drive someone with a different constitution than mine, a higher openness to risk, to chase relationships endlessly, right into the arms of resentment.

Standard Deviant

, writing in Light Rail on the failure that comes from chasing sex in itself or as approval, rather than “engaging in an experience with another conscious being,” notes:

I think that sex without liking women leads to a transaction. And a transactional mindset without successful transactions can lead to resentment. And resentment can be smelled a mile away… But it doesn’t make much sense to be simultaneously aggrieved and trying to play a game where being aggrieved is a large negative signal.

So… that’s it, right? I can understand that. I mean, I’m driven by a desperate need for approval, so it would make total sense if he is, too. He’s just not as controlled as I am, so he keeps running into the glass door, running himself ragged and leaving himself open to be taken advantage of.

That’s Not It

This interaction took place a couple of years ago. It recently came back up in a conversation with a mutual friend about dating — I’m not the only one who’s had this conversation, apparently.

In the interim, I had done a bit of work becoming a somewhat less anxious person, and gotten really fascinated by online dating discourse (despite — or because of? — my continued lack of participation in it). Chewing on it again, it tasted different.

I do think there’s something to the way I thought about this on reception. Idk. Is there?

The second installment will be linked here when it is published.

1. This is what we in the business call “dramatic irony.”