How do I get him to come out of his shell?

[teenystew166]

So, my coworker wants to set me up with her friend's son. He had found me on Facebook and added me, so I'm guessing he is interested. We are all planning on going out to this bar near me some weekend, and I'm definitely looking forward to meeting him.

Here's the deal though:
I'm an extrovert, and he's the polar opposite.
My coworker has told me that he is very shy. This doesn't bother me necessarily, but I've always known guys who were outgoing and talkative, like myself.

My question is, how do I get him to come out of his shell when we all get together ("we all" as in me, my coworker, him, and his mom)? I know to obviously introduce myself and that asking questions about him usually helps a lot, but are there any other tricks to make him feel more comfortable around me?

Thanks in advance for your help!