Potentially Autistic Friend

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So there's this guy friend I have. I used to have a bit of a crush on him, but it's largely gone away now (he didn't feel the same way ). We're pretty sweet friends though so it's okay.

However, I'm really really sure he's either high-functioning or Aspergian, and I want to ask him about it because I'm undiagnosed and have had some crap psychologists in the past. It'd be really cool to have a friend in RL who could relate to some of the problems I have, but I know he'd be hugely self-conscious about it.

Any tips or plans of attack?

One possibility might be, rather than asking first about himself, mentioning your thoughts about yourself. You could say that you've realized that some of your quirks fit into a certain pattern, and that that pattern seems consistent with the idea that you have Aspergers, and then perhaps explain what some of the quirks are, if that fits in the conversation. Or something to that effect.

If he knows he's autistic, that might encourage him to mention it about himself. If he doesn't know - well, he could have a variety of reactions. If your traits are ones he shares himself, he might think "hmm, that sounds like me" - at which point he might start considering the possibility for himself and realize that it fits him, and, like many people, be glad to find an explanation. Though he could also go into denial and say "No! That would be something wrong with me, and I don't have anything like that wrong with me, and so it can't apply to you either!"