I have a theory I really wish I'd used when I first started dating people: take a prospective date to a museum. Not so much for something specific, just a generalized museum that has a little of everything. I've found you learn a lot about someone based on their feelings about art.
Despite living someplace I consider a bit of a cultural wasteland, I still got some exposure to art & theater as a child. I remember going on field trips to the Stevens Center & really liking the architecture. The idea of being able to picture yourself in another time b/c of being around something that's from a long time ago is one of the reasons I picked my college. I even worked at my college's museum for 3 years & I wish I could have gone to Art Expo this weekend since I like looking at art.
One day, I'll be able to afford some. I even have some I'm going to hang if I ever get an office.
Why do I say take someone you're dating to a museum? Because I would have saved myself some serious time & heartache had I done that w/an ex.
When I was in college, Psycho Boy came to visit me. He happens to show up while I'm working at the museum one day. Upon walking in, his first statement to me is "Those people are naked!" & indicating a poster for a prior exhibit where there's a topless woman.
Now personally, I'm not one of those people who makes a big fuss about artistic nudity. I find it tacky & incredibly low class to do so, especially when you're announcing it to the whole world. To make this story even better, my boss walks by & he says loudly within her earshot "That chick is hot!" I said "That's my boss." I don't know whether she heard him or not but if she did, she never told me.
Honestly, a museum separates the cultured from the non-cultured. If you want to call me snotty, fine but I do think I have a little more culture than some of the people I know from my hometown.
I also think aside from figuring out where your potential boy/girlfriend falls on that divide, you also learn about people based on what they like or hate. My husband & I have similar tastes in art, actually. I consider myself comfortable in almost any social setting but I can't really deal w/people who are like Psycho Boy in that regard. At least, I couldn't have a serious relationship w/someone like that or spend huge amounts of time with them.