Jest Not That Into You

Women always say they like a man with a good sense of humor. What exactly does that mean? I think I'm funny. Do I have to bust right out with a bunch of hilarity on the first date?

--A Guy

If a woman agrees to go out with you, it isn't so she can finally find out why the chicken crossed the road. She either wants a free dinner or wants to figure out whether you're worth seeing again. You're unlikely to score a second date by pelting her with jokes and one-liners, which suggests you prepared for the evening by memorizing the joke book on the back of the toilet. What impresses a woman are shows of wit -- spontaneous expressions of humor in response to something she says or something around you. Wit reflects intelligence while communicating your worldview -- telling her who you are far more interestingly than droning on about your major and your dream to someday get your boss to assign you a better parking space. That said, don't get so caught up in making her laugh that you forget that connecting with her is the point. Make her feel like a one-woman audience for your "act" and she'll figure out for herself why the chicken crossed the road. (Because it would rather be hit by a car than listen to another one of your jokes.)