GUYS ONLY PLEASE... Longish but what on earth is going on? : )?

Wow! I can only conclude that he is interested but he has "issues". It is not that hard to simply say "I like you and would like for us to go out" You have invested way too much time in this. I am afraid his "image" and his "friends" are way to much baggage. He is not ready to be a boyfriend yet. He needs to find his own identity and stand on his own feet first. Better find one that knows who he is and is not afraid to be himself. Best of luck.