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How about asking them what they know?

If people aren't sharing these things with you on first date doesn't mean they are blank and have no life experience.

Every passing moment gives you experience. Some experiences might be more interesting to you while others might not be.

They didn't open up to you because they sensed something.

Awkward could be new normal. Can you share what you did to make them less awkward and more comfortable?

Joke around a bit and tell some stories for the first while. You create opportunities for them to comment, or to share a story of their own, but you take the pressure off them 'needing' to respond by having another story or whatever ready to talk about. Its really important to make them feel like there is almost no pressure on them - its the best way to get anyone to loosen up I find.

They eventually open up a lot and start talking freely, it ends up being a fun night, but if you want to hear a good story its just harder to get out of a recent student. I think they were just too busy to go out and do wacky things they could talk about later.

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