Most Helpful Guy
Just ask him out. Ask him when he's alone, so that he doesn't get peer pressured.
Like Pink2000 said, if he rejects you, you'll be right where you started, you won't win, but you won't lose anything either. But if he accepts your offer, you'll be winning a lot. So take the step, ask him to go out on a date with you.
Most Helpful Girl
gosh, this has easily got to be one of the most terrifying things ever. i wish i could do it but it's HARD!