Talking to strangers and making it work is a GREAT social confidence builder. Doing it enough is a good way to learn what works and doesn't as well. I didn't

Talking to strangers and making it work is a GREAT social confidence builder. Doing it enough is a good way to learn what works and doesn't as well. I didn't read much of the original post but what he's doing is a GOOD thing. As for the awkwardness, once he gets over that the other person will feel more at ease as well. Once he is at this point working the room at a conference, interacting with people he met through friends, etc. will be much easier. Being social is a learnable skill, not something a few lucky ones are born with.