Take a chance on me...?

It's not worth it. Don't put yourself out there too much and the reason why I say this is because it seems like now, that you are really pushing it. He told you he wanted to be friends, and now you want to go and tell him that you want to be more than friends. I think you should at least because friends with him again (close friends like yall used to be) and after a while if you still feel the same way you do, then tell him how you feel.