>>4 While I think you're generally right in your thinking that this is a learned social behavior issue, I don't see how medication will help that at all. What he needs is cognitive-behavioral therapy, if he's going to contact a psych.

More than that, though, I think he needs to talk to people he actually knows about his issues and become more comfortable through, as you said, pushing himself a little bit more, and through experiencing that his anxiety isn't that big of a deal. It's a bit odd, but it isn't like "OMG WTF get away from me."

Of course, this all assumes that anxiety related to social situations is the problem. (Though what has been said would also work for anxiety related to sexual issues.)

My question for >>1 is if it's sex that he's afraid of/leery about, or if it's being closer socially/intimacy of communication.