one date idea that i've had more than once, would be to go to an art museum with said other person and make a bit of a game of it. take opposite routes through the rooms and pick a favorite piece, and - optionally - pick which one you think the other will choose for their favorite. then after you've done this for each room, walk through together and see what the guesses and answers were. or have lunch at a cafe and compare notes. [note: it would either have to be a smallish museum or you could just limit the rooms used for the game.]
i'm not sure why it appeals to me. maybe the attempt at understanding the other and trying to assume what interests them. the idea that some might be entirely obvious while others will end up being something you dismissed entirely. i really like the idea of having someone try to express to me why a certain painting in a room is their favorite. even if it ends up being because, "..i hated everything in this room and found this one to be the least objectionable." that'd be good for a laugh.
i'm pretty sure i'm more interested in such an outing than anyone else (which does not bode well for it ever happening), but stranger things have happened. the thought of it might keep me up tonight.
if we keep driving we can not go wrong ..