Let me start by saying that we are both 16 and in 11th grade (juniors). I am NT (f), and he has Asperger's, which told me when we met in 8th grade. We've had lots of mutual friends since then, although we've become closer friends this school year. He's very smart—one of the top students in our class—and is rather extroverted and outgoing, while I'm more of an introvert. I probably wouldn't have ever realized that he has Asperger's if he hadn't told me, but he does show signs: he tends to take sarcasm and jokes literally and not pick up on certain social cues (such as, at times, when to be quiet) as well as avoiding eye contact.
I've never dated before, but he is so easy to talk with and great to be around, and I really like him. I'm very shy, and I doubt he would pick up on any subtle flirting, so what would be the best way for me to communicate that I'm 'interested'? I know he's not necessarily unconcerned with romantic relationships in general; last year he asked a girl out and was crushed when she rejected him. Would directly asking him out put him in a bad position if he isn't interested, or compromise the relationship we have? Our friendship is important to me, and I don't want to risk losing it if I can avoid it. Also, keeping his specific Asperger's traits in mind, is there anything I need to be aware of in a relationship with him?
I've never dated before, but he is so easy to talk with and great to be around, and I really like him. I'm very shy, and I doubt he would pick up on any subtle flirting, so what would be the best way for me to communicate that I'm 'interested'? I know he's not necessarily unconcerned with romantic relationships in general; last year he asked a girl out and was crushed when she rejected him. Would directly asking him out put him in a bad position if he isn't interested, or compromise the relationship we have? Our friendship is important to me, and I don't want to risk losing it if I can avoid it. Also, keeping his specific Asperger's traits in mind, is there anything I need to be aware of in a relationship with him?