just a tip, if you can draw well, I mean really well, and so that you can really nail the likeness, make it a fun activity on the date. Just pick up your sketchbook and say "hey, try to sit still, I know it's hard, but just quick". Then do a quick sketch (that doesn't make her look ugly), chat pleasantly while doing it (only like 5 mins, a little indication, no rendering - told you had to be good). She'll love the attention then because it lasts very little, shows your skills etc. but doesn't come accross too hard.
But that's for HC artists.