100 Questions to Ask Your Parents While You Still Can

Almost everyone who loses a parent describes the same specific regret, and it is never about not saying goodbye. It is about the ordinary facts. What street the family lived on before the move. What their first job actually was. Which of the stories were true. Things that would have cost twenty minutes to ask and are now permanently unavailable.

Below are a hundred questions, grouped by life phase, written to be asked out loud rather than emailed. A note on using them before the list, because the list is the easy part.

How to actually ask these

• Do not send the list. A hundred questions in an inbox reads as homework and gets answered by nobody. Ask five in a conversation and let them run.
• Record it. Phone on the table, say what you are doing, then forget about it. The voice matters more than the transcript in a way that is hard to appreciate until it is the only copy you have.
• Ask the boring ones. What did the house smell like beats what was your proudest moment every single time. Specific and small unlocks memory; grand and abstract produces a summary.
• Follow the digression. If a question about school produces ten minutes about a neighbour, that is the interview working, not failing.
• Write down years afterwards. Whatever else you capture, note the years — when they moved, when the job started, when the person they mentioned was around. The stories survive on their own. The dates do not.

Before you: the family that came first

• What do you know about how your parents met?
• Which of your grandparents did you actually know, and what do you remember of them?
• What did your father do for work, and did he like it?
• What did your mother do all day when you were small?
• Where did the family come from before the place you grew up?
• Was there money, or was there not? How did you know?
• What did your parents argue about?
• Is there a family story you have never been sure was true?
• What language was spoken in the house, and what was spoken outside it?
• Who in the family was not talked about, and why?
• What did your parents want you to become?
• What do you wish you had asked your own parents?

Childhood

• What is the earliest thing you can remember?
• Describe the house you grew up in — start at the front door and walk me through it.
• Where did you sleep, and who else was in the room?
• What did the kitchen smell like?
• Who were you closest to as a child?
• What were you afraid of?
• What did you do all summer?
• What was your street like, and who else lived on it?
• Did you have a pet? What happened to it?
• What was the first death you remember?
• What did you get punished for?
• What did you want to be, at seven?
• What is a small object from that house you would recognise instantly today?

School and coming of age

• Who was your first real friend?
• Which teacher mattered, and what did they do?
• What were you good at that nobody noticed?
• What did you get in trouble for at school?
• When did you first feel like an adult?
• What music was playing?
• What did you and your friends do on a Friday night?
• Who was your first crush, and what happened?
• What did you believe then that you no longer believe?
• Did you ever get badly hurt?
• What was the first thing you bought with your own money?
• What was the last day of school like?

Young adulthood and work

• What was your first job, and what did it pay?
• What was the first place you lived that was actually yours?
• How did you decide what to do for a living — or did you not decide?
• What job did you take only for the money?
• Who taught you how to work?
• What was the biggest risk you took in your twenties?
• Did you ever get fired, or quit dramatically?
• What was the furthest you travelled, and how did you get there?
• Who did you live with, and how did that go?
• Was there a year you would not want to repeat?
• What did you spend money on that you regret?
• What did you think your life would look like at forty?
• What was the best year of that decade?

Meeting, and partnership

• Where were you when you met?
• What did you think of them at first?
• Who pursued whom?
• What did your parents say?
• Where did you go on the first date?
• When did you know?
• What was the wedding actually like — not the photographs, the day?
• What was the first year like?
• What was the first serious argument about?
• What did you learn about them slowly?
• If it ended, when did you know it was ending?
• What would you tell someone about choosing a person?

Becoming a parent

• Where were you when you found out?
• What was the day I was born like from your side of it?
• How was my name chosen?
• What surprised you most about having a baby?
• What were you most afraid of getting wrong?
• What did you do differently from your own parents, deliberately?
• What did you repeat without meaning to?
• What was the hardest year of raising us?
• What do you remember about me that I would not remember?
• What did you give up?
• Was there a moment you were proud of me and did not say so?
• What did you worry about that turned out fine?
• What do you think we misunderstood about you?

The middle years

• What was your working life like at its busiest?
• Which move was the hardest?
• Who did you lose, and what changed afterwards?
• Was there a point where you thought about starting over?
• What kept you up at night in your forties?
• What friendship ended, and why?
• What did you do in those years that nobody in the family knows about?
• When did you first feel old?
• What was happening in the world that you remember from the inside rather than from the news?
• What did you stop caring about?
• What was the best holiday, and who was there?
• Was there a decision you have thought about ever since?

Now, and looking back

• What are you proudest of that has nothing to do with work?
• What do you know now that would have helped you at thirty?
• Who from your life do you think about most?
• Is there anyone you wish you had apologised to?
• What has surprised you about getting older?
• What do you still want to do?
• What should we do with your things?
• What do you want us to tell your grandchildren about you?
• Is there anything you have never told me?
• What was the happiest you have ever been?
• What would you like read at your funeral?
• What was the point of it, do you think?
• Is there a question I should have asked you?

The three that people always wish they had asked

Out of a hundred, three come up again and again from people who ran out of time. They are worth asking first rather than saving for a conversation that may not happen.

"What do you wish you had asked your own parents?" This one does double work. It gets you an answer, and it tells the person you are asking exactly what they are afraid of losing — which is usually the thing they most want to tell you and have never been invited to.

"Is there anything you have never told me?" Almost nobody asks this, because it sounds like it is fishing for a scandal. It is not. It is permission. Most parents are sitting on something ordinary and unresolved — a first marriage, a sibling who died, a job that ended badly — that they have been waiting decades to be asked about.

"What do you remember about me that I would not remember?" The years you cannot access are the years they had you to themselves. This is the only route to them, and it closes completely when they go.

What to do with the answers

The recordings are the raw material. The thing that makes them findable in twenty years is a factual index — the years, places, jobs and people the stories attach to. Without it you have hours of audio nobody will ever search.

That index is exactly what a life timeline is, and building one for a parent is a different job from building your own: you are working from their memory, at their pace, usually across several conversations. We wrote about how that goes on the capturing a parent's story page. If you would rather not run the interview yourself, My Story includes a guided version that asks questions in this shape and files the answers against the right years as it goes.

Whatever you use, the deadline is real and it does not announce itself. Ask five of these on Sunday.