[The Deuce]

My hope is that you have seen it. If you have, just pull a Peter Gibbons, if you haven't read on...
This guy Peter wants to ask this waitress out. So instead of being all cutesy and crap he walks right up to her and says, "I'd like to take you out to dinner." It is actually the plan I have had the most sucsess with. It will catch her off guard, and for some reason impress her. I don't pretend to understand women, and some other people may jump on me for this, but if you tell her what you want she will likely respond positively.