slick it to the side, neat and clean and retro 50's like, and wear a giant bow or blingy barrette on the side.
Or maybe try a pompadour, or curl your bangs in a giant cute girly curl.
(Sorry to reference Paris there... but you get the idea.)
Your date likes you for who you are, and there's no need to wear a wig if you don't want to!
This is coming from someone who knows, lol.