My relationship just ended in the most spectacular fashion. My mother says the best way to get over a man is to get under another man. About three years ago, I was on a terrible date from Plenty of Fish, but the guy was really nice. Here's what I would say: flirt when I'm not around. You're going to lose your friend in the end, so which do you want more, the friend or the guy?
Of course, you're not going to date a 16-year-old when you're twenty, but once you hit your thirties you're in the clear. You can ask for permission, but you're crossing into terrible territory.
Make it a conversation—the two of you talking back and forth—not interviewing.
Thou Shalt Not Drink Too Much I know it's tempting to have a few glasses of wine to relax before or during a date (especially a first one), but keep it at a two-drink maximum.
Whether it's making him dinner, baking him cookies or whatever you can.