I've always liked keeping things real simple. If you guys are going to do the whole music thing, I would find a nice little dive bar with a good juke box. Seriously, some of the best times I've had with girls is hanging out around a juke box in a shitty bar, picking songs, singing, dancing. It's not a classy place so it takes a lot of pressure off both of you and you'll be able to sing out loud without getting any hassle.
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