[MaxWeiss]

She's clearly not a close friend, so go for it. Even if it backfires, you can still be friends if you want, since there's not much to be screwed up!

Do what you want, but from the looks of it, she's into you. You have to act on it, but in a way that makes her think you have the upper hand and are either oblivious to her signals or can see them but don't care because if you go out with her, it's on your terms.

HOWEVER, the day after V-Day is a BAD IDEA, that will just annoy and hurt her, especially if she is into you. V-Day is important and you really kind of HAVE TO do something with her on that day. The trick of course is to do it in a way that it doesn't seem like a desperate move. If you look like every other douche hitting on her on V-Day, you lose. If you don't show up on V-Day, you lose. So you have to take her out, but you have to be very careful about it and keep the power on your side while you are doing it.

That day is all about the fantasy. Not showing up may keep the ball in your court, but she'll just quit playing with you.

You don't even have to take her out. Make her take YOU out--do SOMETHING together, but in a way that's on your terms. Fulfill her fantasy but don't be a weakling.