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if you go to a typical high school, doing band was your first mistake if you're looking to be really popular with a majority of the school. i'm not saying quit band, just it's a ***** to try and be friends with a lot of the athletic type kids if you're in band

Well, I played baseball with this kid and we're good friends now and I've started liking his sister. I know I should ask him if it's ok, but do you think it's a good idea? And how are some good ways to talk to him about it? Cuz I've tried talkin to him about it, just it's really weird, so I...