I don't have a lot of regrets, but one of my major ones is not asking my grandma about her past when she was still willing to talk about it. I've been trying to make up for it by asking my mom & grandpa as much as I can so I don't lose any more family history. Please suggest more things for me to ask!
  1. What was your favorite tv show/radio program growing up? As a young adult?
    According to my mom, her parents never missed an episode of All in the Family. Then we watched an ep together & it was completely fascinating, just from a sociological perspective. Do this with your parents if you never have!
  2. What was the first movie you saw in a theatre?
    I actually did think to ask my grandma this & she told me a very sweet story about her dad taking her to see Snow White. My mom's was Mary Poppins & it blew her little mind.
  3. What was you favorite band/musical artist?
  4. What was your favorite subject/class? Why?
  5. What 'group' were you part of in high school?
    My mom was a geek, but a well-liked geek.
  6. Where were you when Pearl Harbor was bombed/on D-Day/when JFK got shot/during the moon landing/when the Challenger exploded/etc?
    If you're the child of a Boomer, you don't need to ask the JFK one, you've already been told a thousand times. I tried to ask my grandpa what he remembered about the Space Race (my mom was useless) but he just started telling me about how there's a secret alien base on the dark side of the moon (he doesn't have dementia, he's just the 84-year-old version of Fox Mulder).
  7. What was the worst date you've ever been on? What was the best?
  8. Who taught you how to drive? What was your first car?
  9. Tell me about your best & worst family vacations.
  10. How did you meet your spouse? How did the proposal happen?
    Suggested by @ljsee
  11. What was your first job?
    Suggested by @nelle
  12. What were your dreams when young?
    Suggested by @debra47