1. What is your earliest memory?
2. What is something you always wanted to do but never did, and why?
3. How many relationships did you have before you got married, and how did they go?
4. What was the hardest breakup you ever experienced?
5. When did you get your first boyfriend/girlfriend, and did you fall in love with them?
6. What was the best trip you ever took?
7. Was there a moment or event that drastically changed how you see the world?
8. What was the time I upset or frustrated you the most while growing up?
9. What was the hardest fight you had with mom/dad?
10. What is your favorite photo of yourself? And of the family?
11. How do you envision your funeral?
12. How were the early years of parenthood?
13. What was life like when you were my age?
14. What were your biggest challenges in high school?
15. Is this era what you imagined it would be when you were a teenager?
16. How was your wedding day?
17. How was the day I was born?
18. When did you know you were ready to have kids/get married?
19. What do I need to know about our family’s medical history that might affect my health?
20. As a child, what did you dream of doing for a living?
21. What is the most important thing your mom or dad told you in your youth that turned out to be true?
22. Are you at the place in life you thought you would be?
23. When was the first time you remember getting your feelings hurt, who hurt you, and what happened?
24. Who was the first person you said “I love you” to in a romantic context, and what did they say back?
25. If you could have dinner with three famous people, living or dead, who would they be?
26. What were Friday nights like when you were a teenager?
27. When were you the happiest?
28. What’s the best gift you ever received?
29. What time in your life was the best in your eyes?
30. How would you like to be remembered?
A little message to end on:
There are so many things we want to ask our parents, and sometimes we only think of them when it’s too late. If that’s not the case for you, I strongly recommend asking these questions or talking to them about any other topic that piques your curiosity. Even if these conversations feel awkward or uncomfortable, you have no idea what amazing things they might reveal. At the same time, the answers to these questions are something you can share with your children, if they are the right age, and strengthen your bond with them. They may not yet fully appreciate you for everything you are and do. However, if you take the lead and start talking to them openly and honestly, it’s very likely that you will see a change.
