Good way to draw someone out is to comment on something they're wearing.

Make sure it's something they've chosen -

If you say to a tall person 'wow you're tall' you will not only sound stupid and un-creative because they've heard it a million times but they don't have anything profound to say about it because they didn't choose that.

But if you say wow, what a great jacket etc then they can feel proud because you've complemented their taste.