Wes:
1) I too went to a Christian school, and if we were on a field trip and needed to stop somewhere to eat, sometimes a lot of people wanted pizza, but we couldn't stop at a pizza place because they serve beer there. Huh? We were all underaged and chaparoned anyway--what was the chance we would drink? I guess they didn't want us to see someone else drink and get the idea. The administration also didn't allow any physical contact between people who were dating.
2) About the need to listen to non-Christian music and being able to identify with plain old human experience, you should check out a book by John Fischer called "Fearless Faith." Lots of talk about that very thing. Lots of criticism of those who retreat into the Christian subculture because it's safer there.
Jeff