50 Questions to Ask Your Parents Before It's Too Late

The most common regret people describe after losing a parent isn't something they failed to say. It's something they failed to ask.

You can name your grandmother, probably. Can you name hers? Do you know what your father was frightened of at twenty-five, or why your mother left the town she grew up in? That information exists in exactly one place, and it isn't written down.

Here are fifty questions worth asking, organised so you can work through them a few at a time. At the end, some practical notes on recording the answers — because the questions are only half of it.

Childhood and growing up

1. What's your earliest memory?
2. What was your bedroom like?
3. Who was your best friend at ten, and what happened to them?
4. What did you get in trouble for most often?
5. What did a normal Sunday look like in your house?
6. What was the first thing you ever bought with your own money?
7. Which teacher do you still remember, and why?
8. What were you afraid of as a child?
9. What did you want to be, and when did that change?
10. What's something you did as a teenager that your parents never found out about?

Family history

This is the section that disappears fastest. Two generations back is usually the outer limit of what anyone still knows.

11. What were your parents like — not as parents, as people?
12. What do you know about your grandparents?
13. Where did our family come from, and why did they leave?
14. Is there a story about how the family got its name?
15. Who in the family are you most like?
16. Is there anyone the family doesn't talk about?
17. What traditions did you grow up with that we didn't keep?
18. What illnesses run in the family?
19. Are there any family heirlooms, and what's the story behind them?
20. Which relative do you wish I'd been able to meet?

Love and relationships

21. How did you and Mum/Dad actually meet — the real version?
22. What did you think the first time you saw them?
23. What was your first date?
24. Who else was there before? Anyone serious?
25. What was the hardest year of your marriage?
26. What do you wish you'd known about marriage at twenty-five?
27. What did your parents think of the person you chose?
28. What's something about your relationship we never saw?

Work and money

29. What was your first job, and what did it pay?
30. What job did you like most, and which did you dread?
31. Was there a career you wanted and didn't pursue?
32. What was the tightest money ever got?
33. What's the best financial decision you made? The worst?
34. Did you ever nearly do something completely different?
35. What do you wish you'd understood about money at thirty?

On being your parent

These land differently once you have children yourself. Ask them anyway.

36. What do you remember about the day I was born?
37. How did you choose my name? What else was on the list?
38. What was I like as a toddler?
39. What did I do that drove you mad?
40. What surprised you most about becoming a parent?
41. What's something you got wrong with me?
42. Was there a moment you were properly frightened for me?
43. What do you see in me that I probably don't see?

The bigger ones

Save these for when the conversation is already going. They rarely work cold.

44. What's the best decision you ever made?
45. What do you regret?
46. When were you happiest?
47. What's the hardest thing you've been through?
48. Has what you believe changed over your life?
49. What do you want to be remembered for?
50. Is there anything you've never told me that you'd want me to know?

How to actually do this

Most people read a list like this, feel something, and never ask a single question. A few things make the difference.

Don't announce it as a project

"I want to record your life story" makes people self-conscious and formal, and formal answers are worthless. "I've always wondered how you and Dad actually met" gets you the real version.

Three questions at a time, not fifty

This is a series of ordinary conversations, not an interview. Fifty questions in one sitting exhausts everyone and produces shorter answers as it goes.

Record the audio

This is the part people skip and later regret most. Notes preserve the facts; only a recording preserves the voice — the accent, the pauses, the particular way they laugh at their own story. Voice is consistently what families say fades first and is missed most.

Your phone's voice memo app is completely sufficient. Ask permission, put it on the table, and let people forget it's there — most do within two minutes.

Ask the follow-up

The first answer is usually the rehearsed one. The real story is one question deeper: "What was that actually like?" or just waiting a few seconds instead of moving on. Silence does more work than another question.

Start with the oldest person you know

Not because it's morbid — because their information is the least recoverable. A grandparent holds three generations of family history that exists nowhere else.

Related reading

• How to Record an Audio Diary for Your Children
• What Documents Does Your Family Need If You Die?
• Letter to My Daughter on Her 18th Birthday