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On Love And Money: Who Should Pay For The First Dates?

It's easy: both of you.

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In this series we explore the relationship between money and relationships. In the first installment: who should pay when love is at its youngest?

Ladies, just offer to pay. Let go of the expectation that men "should" pay. The Mancession has come (and is slowly leaving). We're not racking up college degrees and killing ourselves for high-powered jobs and equal pay so that when we're out on a date and the check comes we can stare, doe-eyed and vacant, at whoever's across the table until they slap down their AmEx and take care of it like it's the one thing they've been waiting to do all day — spend money on a girl!

Odds are, a lot of men will pay anyway when you offer. But an increasing number of my single female friends always offer to split the check the first time out with someone. One said this just feels like the most natural thing in the age of online dating when you haven't even physically interacted with many of the people you go out with. As this friend put it: "It feels weird to have some random from the Internet spending money on me."

Some women I spoke to said they like to pay because then they don't feel like the guy expects them to return the favor with sex — but if you think every man trying to be polite by paying for your drinks or meal is trying to buy sex, you might try not thinking about your love life as completely transactional. Not all men are like that, really! Some of them are shitty enough to have such expectations, but I'd venture that the majority of them are not!

If you have a long night with multiple stops — dinner here, drinks there — and he picks up the check at the first stop, try to get the bill at the next stop. This way, if you get hammered after a long night out with someone, he won't wake up in the morning and think, "Oh fuck, I blew a bunch of money on that girl" and start passive aggressively texting you things like, "Is it normal for men to spend hundreds of dollars on you on the first date?" Which is something that happened to a friend of mine whose date ended up paying for her dinner and drinks into the wee hours one weeknight that ended at a nightclub. (Maybe also avoid nightclubs on first dates, even as a second or third destination. Do you really want to date Nightclub Guy who's super into the idea of partying at 3 a.m. on a Tuesday? Probably not.)

So you might be thinking, but what if he makes a lot more money than me and wants to take me out somewhere fancy that I can't afford but he can? I would suggest not going somewhere you can't afford. If your date suggests a place whose name would go with four dollar signs in a guidebook, suggest another place. You don't have to say, "I'm poor and I’m not comfortable with you spending $150 on our first (and possibly last) meal together." Just say, "Why don't we grab a beer here at this place closer to my house?" Whatever! He shouldn't be offended (and if he is: WEIRDO), because most of the time people aren't upset about not having to spend a ton of money to impress someone. You don't want to send the message that you're high maintenance and must be paid for and taken fancy places. Besides, if you downgrade a first date to casual drinks, you can get it over with much more quickly and cheaply than a dinner if the guy sucks.

Let's say you start seeing someone and you two avoid all nightclub disasters and make it to four or five dates. Say this romantic interest is a polite sort who insists on paying for your first few dates, which is part of his appeal (not necessarily his willingness to spend his money on you — though that might stir the evolutionary instinct deep in your brain that goes OOH CARETAKER FOR FUTURE BABIES — but his politeness). And I mean he really insists on paying — won't even let you reach for your wallet insists on paying — and so you haven't paid. Well, there are always ways to pay. Go to the bathroom before the bill comes and slip the waiter your card. Call the restaurant ahead of time and give them the credit card number. I've done this and know women who do it. Men REALLY appreciate it. After all, don't you want to be with someone who goes the extra mile like that? Thought so.