Dinner And A Second Mortgage?

I know you've discussed how the guy should pay on the first few dates. I've been dating a pretty fabulous woman for a month, and I'm dipping into my savings to take her out to the sort of restaurants she's used to. I earn a decent living in a creative field, but she is in finance and clearly makes far more money than I do. I may have complicated things when, on our third date, she wanted to pick up the check and I wouldn't let her. Is there a smooth way to let her know that I now need her to throw down some dough?

--Can We Say Awkward?

The organ that gets used on the third date isn't supposed to be the kidney you sold on the black market to pay for dinner. It's nice to take a woman out for a special meal from time to time, but the guy who can keep up the weekly wining and dining at restaurants where even the cockroaches speak passable French isn't the guy you are -- and probably isn't the guy she expects you to be. Women do look for a man to be ambitious and show potential. But typically, a woman who wants a rich guy not only has calculated her date's net worth (probably pretty successfully) long before the first date but has also trained herself to identify a fake Rolex at 50 paces and read even the subtlest signs about a man's income like fiscal tea leaves. So, this woman is probably well aware that if you're "managing a hedge fund," it's just a little money you're putting aside to replace the dead plants on your balcony. Also, unless a man's a spy, a woman doesn't like him to pretend to be somebody he's not. This isn't to say you should have some awkward conversation with this woman about how you really do need her to pay for dinner -- or hope she gets the idea when she sees you standing by the on-ramp with a cardboard sign, "Spare $264.50, plus tip?" Instead, just take her to places you can pay for painlessly and wait until you're in a relationship to talk about money. Though women evolved to look for potential partners to show generosity, you can do that in a symbolic way, simply by treating her to something more affordable -- maybe a ticket to a museum and fancy ice cream afterward -- and by showing generosity of spirit: fairness, kindness, and willingness to do the right thing even when it's hard. A woman who really likes you will really like you when you're treating her to the shoe rental at a bowling alley. Plus, you'll be more fun when you aren't worrying about money, and she'll be more relaxed when she isn't worrying that you'll have to file for bankruptcy if she adds shrimp to her Caesar salad.