For my own edification. I'm really bad at conversation. Make some suggestions
  1. Why
    So often we assume we know why someone we are close to are saying something or believe something. Ask why sometimes. What they say might surprise you.
  2. How do you feel about.......
    Ask about serious things. I get into a rut of getting too comfortable with those I am closest to and forget to glean from them, to pick their brain.
  3. How are you are different this year than you were last year?
    For good or for bad. See that person through their own eyes for a little.
  4. What's your favorite childhood/ teen/ young adult memory?
    If you haven't already asked!
  5. What's one character trait of yours that if you could get rid of today and never have to deal with again you would do so?
    Or the opposite, what character trait would you adopt today and keep for the rest of your life?
  6. What are some of the things you think make you happiest?
    Ask this often. Peoples desires change.
  7. If you could be famous for something, what would you want that to be?
  8. What world/ National news or event has affected you the most in the recent past?