I recently asked a woman out to dinner on a first date. I normally pay for the first several dates, especially if I've done the inviting. We went to Prospect, which I thought was classy and upscale without being too over-the-top (e.g. Gary Danko, etc.). But after cocktails, starters, entrees, wine, and dessert, it turned out to be the most expensive first date I'd ever been on. She offered to split the bill when it came, and I succumbed and let her. But then I called for a second date and I'm getting crickets. Mistake?

He Said: It’s best to keep it traditional on the first few dates, especially if you don’t know each other very well, and that means the guy pays the whole bill, even if the woman offers to split it. Your mistake was picking a restaurant where you couldn’t comfortably manage the entire check yourself and then not sucking it up when the total was higher than you expected.

But something unexpected and positive may come from this episode. While it’s quite possible that there’s another reason why your date didn’t work, if the rest of the evening went well and the main reason she won’t respond to your call is because you accepted her offer to split the bill, you may be better off without her. Women who can’t or won’t express their honest wants and expectations sometimes lay out tests to see how we react. Being more naturally responsive to direct and simple communication, we men often fail to understand when a woman doesn’t really mean what she is saying. If, on the first date, she offered to split the bill but was then turned off when you accepted, imagine the other exams that may await as your relationship develops: “Don’t get me a birthday present this year.”/“I can’t believe you didn’t buy me a birthday present.” “Sure, go play golf this Sunday.”/“I can’t believe you would rather play golf than spend Sunday with me.” Over time most of us learn to navigate our female partner's tests, but a woman who flunks you on the first date for agreeing to accept an offer she made may be more challenging than she’s worth.

She Said: Um, busted. We women do test you guys, both consciously and subconsciously. I'm not sure why, but I think it may have to do with biology and the need to prove to ourselves that the man whose sperm is about to enter us can handle …. well, anything. Including whatever little hurdle or dilemma we can dish up. But this isn't as calculating as it sounds. Trust me, often a woman isn't 100-percent sure what she wants until she sees you act and realizes that what you just did is definitely not it. Often, too, a woman is trying to get along and make nice—unlike you guys, she is raised to negotiate, compromise, and take others' needs into account. Whenever a woman overdoes this urge to make nice, she may find later that she didn't really mean it and her cue will be anger or resentment. But unfortunately, this feeling only comes after she utters the offer and you take her up on it. Painful but true.

The solution lies inside the woman. She needs to get more and more skilled as she matures (and believe me, it's a lifelong process) on where her boundaries truly lie, and speak from her deep instinct about her needs and wants. If your date had done this, I suspect that when the bill arrived, though she probably realized it was quite large and felt an urge to seem sweet and helpful by splitting it, she would have sat with that urge for a few moments and realized, "No. It's a first date, he invited me, and he chose the restaurant. The bill is his." Or, more likely, some little twist in her gut would have just signaled, "No." 

So, did you make a mistake? Yes. And if the bill is the reason she's not calling you back, then she did too, because she missed one of her own cues. But let's not forget that there are about 25 other reasons she may not be calling you back, and there's no way to really know for sure. Next time, pay for the first date no matter what, and let this one go.