[Boris]

Read a book like Wine For Dummies. Then go out and try a bunch of different wines.

As for the date advice, there's lots of pussy masters on this forum that can answer all your woman questions. That being said, if it's the first date you might want to take the initiative and pretend like you know what you're doing with the wine list. Try to find out if your date is much of a wine drinker. If she says no or she only drinks white wine, then order a pinot noir. Otherwise get whatever you want. If you really want to look cool, look to see if a particular wine is served by the glass. If it is, you can ask for a taste before ordering a bottle.