Some times I'd just ask "so what do you do for fun?", and then follow up. People usually like talking about their interests. I don't care nearly so much about their work and family. If they're huge into metal, or play football in a rec league, I want to know.
If you're lucky, one of their funs will be something you can talk about.
I would recommend sticking with that strategy and working on it. Going too "spicy" too soon is risky, and doesn't really pay off better than finding someone who clicks with you on medium heat topics like "you saw Caroline rose play?? How was it?"
My girlfriend says that it's often more about flow than content. A well executed conversation about a common topic will go farther than an awkward foray into "so you ever done coke?"