10 questions I wouldn't ask, though the answers might be interesting
Such a fun concept for a list. Thanks @DrFritzS for the inspiration!
1. Tell me about your childhood trauma.
2. Which of the seven deadly sins most applies to you?
3. How hygienic are you?
I really wish it were okay to ask this one.
4. What's your most embarrassing memory?
5. Would you rather...
e.g. quack like a duck every time you laugh or break dance every time you sneeze?
6. What are you most afraid of?
7. What's the saddest thing you've experienced in your life?
8. What are your best and worst experiences with drugs?
9. What's the worst crime you've committed?
Alternatively: what's the worst thing you've ever done? Focusing on morality, rather than the law.