A few years ago, I went out with a woman three times in a couple of weeks. We had great chemistry, and despite the fact that I was a customer service representative at JDate pulling in barely $30K, I’d paid for everything. First date was $60. Second date was $90. The third date was brunch the morning after the second date. She’d ordered a dozen bagels and then realized she’d forgotten her wallet. No big deal. An innocent mistake. She generously offered to pick up our next date.
She called me at work the following day to tell me of a play that sounded like fun. She said she was busy at work and asked if I could find out if there were tickets available. No problem. I called the theater and learned there were only six left. What’s a guy to do? No big deal, I bought a pair of tickets and figured she’d pick up dinner before we went out.
After our $40 meal, she put down her credit card and went to the bathroom. When she came back, she noticed that I didn’t put in my credit card to pick up or split the check. Upon which she glared at me and said, with a ton of venom and not a shred of irony: “What am I, your sugar mama?!”
Being generous, especially to someone you care about, is an incredible feeling – right up there, I’m told, with having everything paid for by someone else.
Yeah, being a guy isn’t always the most rewarding thing in the world. But what are you gonna do? I’ve stopped wondering about what’s “fair” and have decided to embrace the system I’ve inherited. In this system, a guy pays unquestionably, and if a woman offers to pay, he is supposed to say no. At least on the first few dates. Or as long as she’s being courted. Or maybe always. It depends on the woman. We can never know unless we let down our guard and allow her to pick up a check. And by then, it’s often too late to justify your behavior.
This is a quandary all right and there is no one right answer. Until now. As your friendly neighborhood single dating coach, I’m going to give you the definitive rulebook on how to negotiate this tricky territory, once and for all….
WHAT PEOPLE SAY:
HER: He should WANT to pay for me.
Yes, and, generally, that is the case. Being generous, especially to someone you care about, is an incredible feeling – right up there, I’m told, with having everything paid for by someone else. The one time I forgot my wallet on a date, she gracefully picked up the check and told me not to worry. This was both extremely classy, and extremely appreciated.
HIM: She EXPECTS me to pay for everything.
Yes, and that’s the precedent that was established way before you were born. Don’t fight it, just do it with a smile, ’cause if you don’t, you ain’t getting another date.
HER: He SHOULD pay, especially at the beginning.
This logic is a little dicier. Why should a man pay? Because it’s chivalrous? Consider that chivalry started at a time when men worked and women didn’t. Women, literally, could NOT pay. Thus, men picking up the check sprung out of necessity, not out of kindness. It has since been codified into a gentleman’s code, which is considered in very poor taste to question. I’m not questioning, but see how angry you are that I’m even bringing it up?
HIM: But SHE asked me out.
So what? If etiquette says that you pay for the first date, and she expects you to pay for the first date, and you can afford to pay for the first date, then pay for the damn first date.
HER: It doesn’t matter what he makes. A gentleman always pays. It indicates how he feels about me.
If you offer to split, and he lets you split (or even pick up) the check, he has done absolutely nothing wrong.
If a guy makes a ton of money, I can assure you, it’s his absolute joy and pleasure to spring for every last drink and spa treatment. But there’s a big difference between being cheap and being poor. Cheap means the guy asks the woman to pay for the fish when he ordered the less expensive chicken. Poor means that the guy has trouble making rent if he has to pay for five dates in a month. Put yourself in his position: it’s hard to blame him for wanting to alternate checks.
My solution is, not surprisingly, an equivocation. Let’s all try to understand one another.
Guys, be as generous as possible, not only because she expects you to, but because it’s genuinely rewarding to “be the guy” and make life easier on her.
Women, be sympathetic to the grad student or schoolteacher that doesn’t have the means to be as chivalrous as he’d like. You may not be our sugar mamas, but please don’t take it for granted that we’re your ATM’s, okay?
Postscript: A version of this article was written five years ago. Since that time, I find myself in a much greater position to be generous. I remain sympathetic to men who can’t blindly pick up every single check.
My slightly revised position for who pays on a first date is this:
He grabs the check immediately.
She does the “fake reach.”
He waves her off and insists on paying.
She thanks him for his generosity.
End of scene.
Presuming the man can safely afford it, this script should play out on every date during the courting phase.
You, as a man, can’t get mad if she doesn’t make the offer to split. If you offer to take her out, expect to pay for the whole thing, and be pleasantly surprised if you don’t have to.
You, as a woman, can’t get mad if he accepts your reach. If you offer to split, and he lets you split (or even pick up) the check, he has done absolutely nothing wrong. It’s not a game or a test, unless you treat it like one.
One final, overriding note for men: It doesn’t matter if it’s coffee or dinner, whether you make more or she makes more, whether you asked her out or she asked you out. You can never go wrong by paying.