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?!"

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….

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