Reddit top comments...
"What was your first pet?" or "Who was your favorite teacher?" Then read all of their emails.
"You like Huey Lewis and the News?"
what's your reddit username?
Instead of "what do you do?", I quite like "what gets you out of bed in the morning?"
What would your best friend say is your worst quality?
There are [36 questions](https://www.nytimes.com/2015/01/11/fashion/no-37-big-wedding-or-small.html?_r=0) that people can answer together to get to know one another better. The idea behind the 36 questions is to see if you are romantically compatible, but I've done it with friends for kicks and it definitely gave me a better understanding of them.