I love to ask people about their first cars! It's a subject that almost always warrants some sort of funny story and it's also something different that many people don't ask about.
It's lighthearted, catches them off guard and then I follow it up with something like....
That's super hilarious, so, unrelated - Where do you stand on the death penalty? LOL.
Ok, here are some more things I like to ask someone.....
What subject did you really kick ass at in school? Was it because you had a good teacher or a genuine appreciation for the subject?
If you had to sacrifice one of your favorite physical aspects to deformity, what would it be?
Do you think people talk to each other or at each other? Which then I lead into finding out about their listening skills and how they perceive themselves to be as conversationalists.