should i speak with him or just leave him alone?

[Brad]

I would continue to speak with him. I just wanted to point out that he is probably one of those guys who have esteem issues. Why I say that is because you wrote something here that made me think that he was downing himself. Also guys who aren't content with themselves normally smother themselves with Music because it makes them feel better about themselves. It seems like you guys have some sort of bond from what I have read. It seems like you might be able to get a lot out of being a good friend or even at some point maybe even a girlfriend if that's what your intentions are. He seems like a nice guy anyways so I would recommend to continue talking to him!

Keep in mind that he has a low self esteem so watch what you say. Try and make him realize how wonderful of a he person is. Even if you don't like him its just the morally right thing to do.