Guide to Guys: It's On Me

Last week, my friend April, who writes for The Stir, asked me and my friend Liz to answer a question for this week's He said/She Said Column. The question: who should pick up the check on a first date?

You can find April's column here, Liz'a She Said post here, and my complete ramblings below the ancient logo for what used to be a "game show," but which would now get produced as a Reality Series:



Sorry; a question? Sure. Shoot.

What's that, you say? “Who should pick up the check on a first date?”

Hmm. Let me give this absolutely no thought at all. My automatic answer: if it’s a date, the guy picks up the check, because that’s how you know it’s a date in the first place. Or at least that’s how you know the guy thinks it’s a date in the first place, or wants it to be. Picking up the check is a signal of intention and interest. It’s the guy saying, “I’m not just looking at you as a friend.”

But it’s also a sign of respect, in a way that has nothing to do with romance. When I say, “Do you want to go out to dinner?” and you say, “Yes,” then that means I’m paying. Why? It’s all part of the package. We wouldn’t be sitting across from each other sharing a meal if I hadn’t popped the question, and picking up the check is understood as a given the moment I hear your “Yes.” It’s not even an option. Think chivalry.

Of course, chivalry may seem quaint and even sexist in our courtesy-challenged society, but again, it’s a sign of something. All first dates take place in a Signals Bar. Everything I do and say will be interpreted a hundred different ways, like a speech at the United Nations. If I pick up the check, it says a couple of interesting (and hopefully interest-related) things about me. (Like, y’know, “Look out, girls--he’s a man with a job.”) If on the other hand I say, “Let’s split it,” that says something, oh, half-interesting at best (which implies half-uninteresting, and lemme tell ya--if you’re more than 40% uninteresting on a first date, it’s the kiss of death). And then, if I’m stupid enough to say, “Your treat, right?” or, “You had the $30 dollar special which means you owe me--wait--hang on a second while I pull up the calculator app,” or, “So is it okay if I leave the tip?” then that is what most women politely call a deal-breaker and profanely call something else entirely.

Another deal-breaker is the guy who goes into a first date saying to himself, “I will only pick up this check if there’s a spark,” or, “I’ll pay if I think this is going somewhere other than two separate cab rides home.” This guy you do not need, ladies--any hint of quid pro ho is a sign that you are having dinner with someone who is totally prepared to dump you for somebody younger or prettier at the first available opportunity. Since his feeling is that a date is like a high-risk investment, that means he orders the wine believing that he’s owed something in return, and if he doesn’t get it, then he’ll put his money somewhere else. (This probably also means that he’s involved in insider trading, and treats his secretary like crap. Run; don’t walk.)

The point is, dating is not an investment. In reality, dating is a gamble. It’s like a game of poker--you raise, you call, and you always pony up to see the other player’s cards. And once that game starts? That’s when it gets really interesting. Once I raise the stakes, it is then up to the woman to decide whether she calls or raises back. The call would be by saying, “No, let’s split it.” The raise would be by either making a half-hearted attempt to pay and then backing down, or by saying, “If I had known you were pickin’ up the tab, I would have ordered that Johnny Blue.”

And, like poker, if you raise? The game continues. But if you call? The hand is over. If a woman insists on paying half, then there is no date. As a guy, if someone I’m interested in throws down a couple of 20’s and says, “No, I insist, this is for my half,” that translates in my brain as, “I am not interested in you romantically.” And I’m fine with that; in fact, I’d rather hear that than the actual words, “I am not interested in you romantically,” because the actual words hurt like hell. That’s why, when a woman says she wants to pick up half the dinner tab, it’s the rejection equivalent of French: a really nice way to say something that in reality sounds like a slap in the face.

But--and I cannot say this strongly enough--it is also a heart with a line drawn through it, which is the universal symbol for NOT INTERESTED. So if I do continue seeing this woman, it will have to be as friends, unless I want to delude myself into thinking that through the liberal application of persistence and three-course dinners, I can get her emotional barometer to swing from COLD AND DISTANT to HOT AND HEAVY. And don’t think I haven’t spent years paving a road through that emotional jungle, okay?

Oh. You too? Really?

Interesting. Want to talk about it over dinner?