Questions to ask your parents
1. What was your childhood like?
2. What were you like in high school?
3. What did you discover in the last decade or two that you wish you discovered sooner?
4. Favourite place you have lived?
5. What were you doing when you were my age?
6. What advice would you give your 40-year-old self?
7. When did you know that you wanted to marry mom/dad?
8. Tell me the story about my birth.
9. What kind of parent did you think you would be? And what kind of parent do you think you ended up being?
10. What was your biggest fear about raising kids?
11. What do you think I missed out on growing up when I did, versus had I grown up when you did?
12. Did you ever want more children?
13. What’s your favorite thing about being a parent?
14. What’s something about you that has nothing to do with family that you love about yourself?
15. What are your goals now that you aren’t my caretaker anymore?
16. What was something you took away from how you grew up that you either wanted to replicate, or never do as a parent?
17. What do you wish you made more time in your life for?
18. What do you wish you spent less time doing?
19. How would your parents have described you?
20. When you think about a fork in the road in your life, what was it and why did you choose that particular path?
21. What happy memory will you cherish forever?
22. What was your second choice for my name?
23. What have you always wanted to tell me, but haven’t had the courage to?
24. Growing up, who inspired you the most?
25. If you had to do it all over again, would you pursue the same career path?
26. What is your biggest regret?
27. Best trip of your life?
28. What’s one of your earliest memories?
29. What’s the most trouble you’ve ever gotten in?
30. Was there something your parents did when you were a kid that you swore you’d never do yourself?
31. How many serious relationships were you in before you settled down (if you did)? What were they like?
32. What was your hardest breakup like?
33. Growing up, what did you think you wanted to do for a living?
34. How have your notions of what it means to be a woman changed over your lifetime?
35. (If she worked): What was it like being a working mom at that time? Would you do it all over again? What would you change?
36. (If she didn’t work): What was it like being a stay-at-home mom at that time? Would you do it all over again? What would you change?
37. Who were/are your role models? Who did you look up to when you were younger? Who do you look up to now?
38. What’s the best trip you’ve ever taken?
39. What’s the worst fight you ever had with my dad?
40. What’s your favorite photo of yourself? Of our family?
41. What was the first year of motherhood like for you?
42. What do you want or wish most for your kids?
43. What do you want your funeral to be like?
44. What was life like for you at my age?
45. What were some of your biggest struggles or insecurities in high school?
46. Do you have any health issues you’ve never told me about?
47. What was your relationship with your own parents like?
48. What’s someting you always wanted to do but didn’t ― and why didn’t you?