What risk are you happy that you took?

People, even shy people, love to talk about themselves. Here's a question that may help you open someone up:

What risk are you happy that you took?

Don't be surprised if you get some strange responses to this one. Ask well!

What's a place you'd love to travel to someday?

There are lots of things that you don't know about people. Here's a question that may help you learn more about someone:
What's a place you'd love to travel to someday?

Make notes about how people react to the question as well as what their answer is. Good luck!

What random act of kindness could you perform right now?

Asking questions shows that you're interested in others. Here's one you might find useful:

What random act of kindness could you perform right now?

Be sure and use active listening techniques as people answer. You'll learn much more that way!