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50 questions to ask your grandparents

Last updated 2 September 2026

Most of us ask the same three questions — how was your day, are you keeping well, do you need anything. Then one day the person who remembers everything isn't there to ask any more.

Here are fifty questions that actually open something up. You won't need them all. One good one, asked at the right moment, is usually enough — the rest of the afternoon takes care of itself.

Childhood

1. What did your street look like when you were small?
2. Who did you play with, and what did you play?
3. What did your mother smell of — perfume, baking, cigarettes?
4. What was the naughtiest thing you ever did?
5. Were you ever properly frightened as a child?
6. What did you get for Christmas the year you remember best?
7. Who was the strictest teacher you had?
8. What did Sunday look like in your house?
9. Did you have a nickname? Who gave it to you?
10. What was your bedroom like?
11. What did you want to be when you grew up?
12. Was there an animal you loved?

Growing up

1. How old were you when you first earned money, and what did you spend it on?
2. What did you wear when you wanted to look good?
3. What music was playing when you were seventeen?
4. Where did everyone go on a Friday night?
5. Did you ever get in trouble with your parents? What happened?
6. Who was your best friend, and are they still about?
7. What did you argue with your mum and dad about?
8. When did you first feel grown up?

Love

1. How did you meet?
2. What did you think the first time you saw them?
3. What was your first date — and did it go well?
4. Who said it first?
5. How did you propose, or how were you proposed to?
6. What was the wedding day actually like — not the photos, the day?
7. Was anyone against it?
8. What's the thing about them you'd never change?
9. What's the hardest patch you got through together?

Work

1. What was your first proper job?
2. How much were you paid, and what did that buy?
3. Who did you learn the most from?
4. What did your hands look like at the end of a shift?
5. Was there a day at work you'll never forget?
6. Did you ever want to do something else entirely?
7. What were you good at that nobody knew about?

Home and family

1. What was the first place you lived in on your own?
2. How did you feel the day you became a parent?
3. What did we do as children that drove you mad?
4. Which relative should I have met, and why?
5. Is there anyone in the family nobody talks about?
6. What do you know about where our family came from?
7. What's the story everyone in this family tells wrong?

Looking back

1. What are you proudest of that isn't a person?
2. What's changed most in your lifetime?
3. What did you worry about that turned out fine?
4. Was there a moment your life turned on?
5. What would you tell yourself at twenty-five?
6. What do you hope we remember about you?
7. What's a perfect ordinary day, to you?

How to actually use these

Don't work down the list. It turns a conversation into a form, and people answer forms in one word. Ask one, then get out of the way — the good bit is almost always the tangent, not the answer.

Ask about things rather than feelings. "What did the kitchen look like?" gets you further than "were you happy?", because a person can see a kitchen. The feeling arrives on its own, usually halfway through the description of the lino.

And when they say "oh, you don't want to hear about that" — you do. That's the one.