Dr. Michael Aaron, Ph. D., psychotherapist/sex counselor: You’re in good company—flirting is a learned skill for most people, but it all starts with humor. If you can make her laugh without coming off as a clown, you’re on the right track.
Also key: showing genuine interest in her. If she comes away thinking this is an interesting, funny guy who’s also interested in her, that’s a win-win.
Jena Friedman, Writer/Stand-Up Comic: Yes, most women do respond to humor. But what we really respond to first is looks. If you’re gorgeous, you can walk up to us and say pretty much anything short of “Drink this” and we’ll swoon.
If you’re not, you’ll need to use your personality, and that’s where humor can be effective—unless she’s a comedian. As someone who tells jokes for a living, I tend to go for the misanthrope who makes me cry, or tells me something terrifying. Nothing gets my guard down better than being told an asteroid’s about to hit.
But that’s just me. If she’s not a comic, humor’s a safe bet. Maybe tell her she looks like someone you know—sorry, someone you’d like to know. Get it? That’s cute.
Or guess she’s under 21 and ask to see her ID. Women love hearing they look young; plus, that way you can see if she’s an organ donor, and if she is, ask her if she really trusts that if she’s on the operating table someday, a shady surgeon won’t pull the plug just to harvest her organs.
It’s an edgy move, but it’ll get the conversation going.
Another way to get in her good graces: If it’s an event with a cash bar, see what she’s drinking and send her one. (Just make sure she knows you had no contact with it prior to sending it over or things could sour faster than you can say “Cosby sweater.”)
Sure, the drink thing is cheesy, but so is courtship. If she accepts it, wait for a sign, like a little smile or a wave, then strike up a conversation and feel it out from there.