The best questions to ask your grandparents are open-ended ones that invite stories rather than yes or no answers. They cover the themes that matter most: their childhood, school days, how they fell in love, their working life, the history they lived through, and the wisdom they have gathered over a lifetime. The 90 questions below are organised by theme so you can start anywhere and go as deep as the conversation allows.
A survey of 2,000 UK adults found that 67 per cent regret not asking their grandparents more about their lives before they passed away. A further 41 per cent wished they had asked about wartime experiences. Fewer than one in three people have ever recorded or documented a conversation with a loved one - and nearly half of those say they regret not doing so with someone who has since died.
Most of us assume there's time.
Time to ask grandad about the war. Time to hear nan's version of how she and grandad met. Time to write it all down. There always feels like there's another Sunday, another Christmas, another quiet afternoon when the stories will finally get told.
Then one day, they aren't.
The questions below won't make that conversation easy. Nothing does. But they give you somewhere to start - a list to pull out on a quiet afternoon, a prompt for a phone call that goes somewhere you didn't expect, a reason to sit down and actually listen.
There are 90 of them. You won't ask all of them in one go, and you shouldn't try. Pick three or four. Let one answer lead to the next. The best stories rarely come from the questions you planned.
Chapters of You
These 52 questions are the same ones Chapters of You sends your grandad - one a week, by email, for a year. He answers at his own pace. At the end, his stories are printed in a hardcover book for you to keep forever. No writing required on his part. Just an email, once a week.
Their Childhood and Early Life
The earliest years are often the most vivid - and the least talked about. Ask about them before the details start to blur.
- What is your earliest memory?
- Where did you grow up, and what was the place like?
- What did your home look like - how many rooms, who slept where?
- What did a typical Sunday look like when you were young?
- What games did you play as a child, and who did you play them with?
- Was your family comfortable growing up, or did money feel scarce?
- Did you know all the families on your street? What were the neighbours like?
- What did you eat for Sunday dinner when you were young?
- Who was the person in your family who made you feel safest?
- What did you want to be when you grew up - and when did that change?
- Were you close to your own grandparents? What do you remember most about them?
- What was the naughtiest thing you ever did as a child?
- Was there something you collected or obsessed over when you were young?
- Is there a smell, a song, or a sound that takes you straight back to your childhood?
- What's something about the way you were raised that you're most grateful for?
School, Friends and Growing Up
These years shaped who they became - and most families never think to ask about them.
- What was school like for you - did you enjoy it, or were you desperate to leave?
- Who was your closest friend growing up, and what happened to them?
- Were you more of a leader or a follower at school?
- Did you ever have a teacher who genuinely changed the way you saw things?
- What subject came naturally to you, and which one felt impossible?
- When did you have your first job, and what was it?
- What did Saturday nights look like when you were a teenager?
- What music were you obsessed with when you were young?
- Did you ever get your heart broken before you met [partner's name]?
- What's the biggest risk you took when you were young - and did it pay off?
Love, Marriage and Family
The stories nobody tells until someone asks.
- How did you first meet [nan / grandad / partner]?
- When did you know they were the one?
- What did your wedding day look like? What do you remember most about it?
- What's the most difficult thing you've navigated together as a couple?
- What's your best piece of advice for making a relationship last?
- What kind of parents were your own parents - and how did that shape you?
- What do you remember about the day [your children] were born?
- What was it like when your children left home?
- Is there anything you wish you'd done differently as a parent?
- What surprised you most about becoming a grandparent?
- What do you hope your grandchildren remember about you?
- Did you ever have to make a real sacrifice for the people you love - and was it worth it?
- What does love look like to you, day to day, in practical terms?
- Is there someone in the family you've always quietly worried about?
- What advice would you give to someone getting married today?
A note before you continue: if some of these questions are going unanswered - because your grandad types slowly, or your nan doesn't know how to begin - that's exactly the problem Chapters of You was designed for. We handle the questions, the prompts, the pacing. You get the book.
Work, Career and Purpose
What they built, what they gave up, and what they'd do differently.
- What was your first proper job, and how did you end up there?
- What's the work you've done that you're most proud of?
- Was there a career path you never pursued but always wondered about?
- What did you learn about money the hard way?
- Did you ever have a boss who made you genuinely better at what you did?
- What's something you built, created or achieved that you want people to know about?
- If you could go back and do your working life differently, what would change?
- Did your sense of purpose come more from work, or from somewhere else - family, community, faith?
- What's the hardest professional decision you ever had to make?
- Do you think people today have a healthier or unhealthier relationship with work than your generation did?
Chapters of You
Give your grandparent a structured way to answer questions like these - one a week, for a year. Chapters of You sends a thoughtful prompt by email every week. They reply when they feel ready. By the end, their answers become a beautiful hardcover book.
The World They Lived Through
They witnessed history that your children will only read about in books.
- What major event in your lifetime has shaped you the most?
- Do you remember where you were when [a significant event] happened?
- What was it like growing up without [technology that defines your grandchild's world]?
- How did your town or community change over your lifetime - for better and for worse?
- What's something people in your generation understood about life that younger generations have lost?
- Have you ever been truly afraid about the state of the world?
- What did you think the future would look like - and were you right?
- Did you ever experience prejudice or injustice, yourself or toward someone you loved?
- What's the best thing that's changed in your lifetime?
- What do you think we've lost as a society that we didn't notice going?
- Is there a period in history you wish you'd been alive to see?
- What would you want future generations - who never got to meet you - to understand about your time?
Wisdom and Life Lessons
The answers most worth writing down.
- What do you know now that you wish you'd known at 25?
- Is there a decision you made that you've spent years wondering about?
- What does a good life look like to you?
- What's the bravest thing you've ever done?
- Is there something you deeply regret - and have you made peace with it?
- Has your faith - or your lack of it - ever been tested?
- What's the kindest thing anyone has ever done for you?
- What's something you believed when you were young that you no longer believe?
- If you had to name the three things that have mattered most in your life, what would they be?
- What does loyalty mean to you?
- Is there someone you've never fully forgiven?
- What advice would you give to someone starting a family today?
- Have you ever felt truly at peace - and when?
- What do you want people to say about you when you're gone?
- What would you tell your younger self, if you could?
Questions to Ask Your Nan
Questions written for the woman whose stories are often the least told.
- What was it like raising a family in the era you did?
- Did you ever feel you had to give something up for your family - and how do you feel about that now?
- Is there a recipe, or a piece of knowledge about how to do something, that you want to make sure isn't lost?
- Who were your female role models when you were growing up?
- What's something you're most proud of that nobody ever gave you credit for?
- What does being a nan mean to you?
- Is there something you've kept private your whole life that you'd finally like to say?
- What do you want your grandchildren to know about the woman you were before you became their nan?
Questions to Ask Your Grandad
Questions that get past the short answers.
- Is there a moment in your life when you felt, in the truest sense, like a man?
- What did your own father teach you - not by words, but by example?
- What's something you've carried quietly that's been harder than people realise?
- What does being a grandad mean to you?
- What would you want your grandchildren to carry forward - a value, a habit, a way of seeing the world?
What to Do With the Answers
Asking is one thing. Keeping the answers is another.
The simplest approach: record the conversation on your phone. You don't need a microphone or an app. Put your phone on the table, press record, and let them talk. Listen to the file back later and you'll be grateful you did.
If you want something more - something that turns their answers into a book the whole family can keep - that's what Chapters of You was built for.
Chapters of You
Chapters of You sends your grandparent 52 guided questions, one a week, by email. They answer at their own pace - by typing, or by speaking and letting our app transcribe. At the end of the year, their answers are beautifully typeset and printed in a hardcover book, delivered to your door.
No writing required. No complicated technology. Just a question, once a week, from someone they love.