So I notice that a big problem I have, and a problem many socially awkward people have is how to approach someone. How to make small talk, things of that nature that seem like they should come natural are often difficult to..well the more nerdy of us.
I just recently came out of my shell, and I'm still having trouble, so I've developed, and read about some methods to help with the most basic of social interactions.
So that gives me one very easy opening to get into conversation; "Do you have a lighter?"
It's simple, and it works. Conversation has been initiated, and through that you can ask the basic questions, the Who, where, and such.
Another strategy is, if you are a social gathering, to find out who the person is ahead of time.
"Oh, you're ________, right? Yeah ______ mentioned you."
And from there, you can build.
a third rather popular item is to find someone on someones person and ask about it.
For example, I wear a bobby pin and a rubber band around my wrist, soley so people have something to say if they want to talk to me. To do away with that initial awkwardness.
"Okay, dude, I hate to ask, but why do you have a bobby pin on your wrist?"
and there, he's in. Conversation initiated, the initial awkwardness is gone.