You sound like a friend of mine, she and I were good friends for about year then we became distant and now we're hanging out again, main difference between you and her is that she currently has a boyfriend. I can't tell you if she has romantic feelings towards me, but we definitely share something more romantic than just being friends. If you want to go out with him, then ask him out that's how I would prefer it the female first it may seem a weird concept, but what's the difference asking someone out is asking someone despite what gender they may be. You just have to remember someone with AS, BD, or any psychological condition will definitely be a cold at the core as an individual, no matter how warm his heart may be, he went through a break up and being rejected the first time by someone he cares about, that's the point of view I come from and it's very painful. After I was rejected by the girl I thought that would be it, that I'd never see her again and we would never have any kind of relationship from then on and he might feel that way since you rejected him the first time he asked you out (not that it was your fault, you just didn't want to go out with him at the time) he may think that no matter what there's no chance with you. So ask him if he'd like an official relationship with you, make sure to show him how much love and affection he would feel if he was with you, and if you feel that same affection back from him, then you got yourself one damn fine boyfriend!