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dating coach for smart, strong, successful women Evan Marc Katz
Years ago, I went out with a woman three times in a couple of weeks. Even though I was making $30,000 as a customer service representative at JDate, I’d paid for everything, including two $75 meals and a dozen bagels one Sunday morning when she’d forgotten her wallet. Generously, she offered to pick up our fourth date.

She called me at work the next day to tell me that she heard of a play that sounded like fun. She said she was busy 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 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?!”

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 egalitarian behavior.

This is a quandary, all right, and there is no one right answer. As a guy who’s been on far too many dates, I’ve heard all the stories from both sides and every angle. But since logic doesn’t seem to get much play in this realm, I’m gonna give it some face time.

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.

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.

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 and treat you like the princess you undoubtedly are. But there’s a big difference between being cheap and being poor. Cheap means the guy asks his date 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 to be. You may not be our sugar mamas, but please don’t take it for granted that we’re your ATM’s, okay?