10 questions I wouldn't ask, though the answers might be interesting

Thanks @sqadir for the branch and @DrFritzS for starting this one. 

1. How much do you earn a year

2. Do you like me

3. How have you cheated on your significant other

Emotional cheating is a thing. People may also consider going to a strip club or watching pornography cheating

4. Do you use people?

5. Do you have any real friends?

6. What’s the most dangerous thing you’ve ever done?

7. Who in your life offers the most value? Who offers the least?

8. Do you fantasize about me?

9. Would you trade $10 million for your current life?

10. If you had to pick 1 dictator(currently dead) from the past to be our next president who would it be?