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Questions to Ask Your Grandparents

Most of us know our grandparents as grandparents. We know the kitchen, the chair, the way they say our name. We often know much less about the person they were at ten, at twenty, or on their first day at work.

Good questions are the easiest way in. You do not need a recorder, a notebook or a special occasion. You need a few minutes, a comfortable place and a question that is easy to answer.

This guide gives you 30 questions grouped by theme, a few tips on how to ask them, and a short note on what to do with the answers.

Before you start

Begin with the easy ones. A house, a game or a favorite dish is easier to talk about than a feeling. Concrete memories open the door to the bigger ones.

Let them skip. Some memories are private, and some are painful. “We can skip that one” should always be a real option, and you never need to ask why.

Ask one question at a time. Then wait. A pause is not a problem. Many people need a few seconds before a memory arrives.

Follow the story. If your grandmother mentions a dog, ask about the dog, even if it is not on your list. The best part of an interview is often the question you did not plan.

Childhood and home

  1. Where were you born, and what was the house you grew up in like?
  2. What did you do on a normal day when you were ten?
  3. What games did you play as a child, and who with?
  4. What do you remember about school? Was there a teacher you liked?
  5. What was your favorite thing to eat when you were small?
  6. Did you have a nickname? Where did it come from?
  7. What did your street or village sound and smell like?

Family and the people around you

  1. Tell me about the people who raised you. What were they like?
  2. How did your family celebrate holidays?
  3. Is there a dish or a recipe that tastes like home?
  4. Was there a family saying or a song everyone knew?
  5. Tell me about a friend you will never forget.

Work, skills and pride

  1. What was your first job, and what was your first day like?
  2. What work are you proudest of, whether in a job, at home or elsewhere?
  3. What is something you learned to do with your hands?
  4. Who taught you the most about work, and what did they teach you?

Love and friendship

  1. How did you meet someone you came to love?
  2. What did you do for fun when you were young?
  3. What music or songs take you back?

Questions 8, 12 and 17 can touch deeper feelings for some people. Ask them gently and let your grandparent decide how far to go.

Places and change

  1. Tell me about a journey or a place that changed you.
  2. What is the biggest change you have seen in the world?
  3. What was the first piece of technology you remember? What did you think of it?
  4. What do you miss that is gone now?

Lighter moments

  1. What is the funniest thing that ever happened to you or your family?
  2. What is the best trouble you ever got into?
  3. What would you want to try if you had a free week tomorrow?

Looking back and forward

  1. What are you most grateful for?
  2. Is there a mistake you learned from, and what did you take from it?
  3. If you could live one day again, which would it be?
  4. What would you like the next generations of your family to know?

Questions 28 to 30 are more reflective. They work best near the end of a conversation, once you are both relaxed.

How to ask so that people want to answer

Say why you are asking. “I would like to know more about your life” is a kind sentence and a clear one. It tells your grandparent that this is interest, not a test.

Keep the tone of a chat. Read the question in your own words, and change anything that sounds stiff. If a question lands badly, move on without comment.

Ask about their own memories. Questions about other people’s health, money or private matters are best left out, and they are not yours to ask for someone else.

Do not correct them. If a date is wrong or a name is mixed up, let it be. A story told with the wrong year is still their story, and you can check details later if you want to.

Listen for the small things. A smell, a street name, a sentence their mother used to say: these details are what make a story feel real years later.

Keeping what you hear

Write it down soon, in their own words where you can. If you record a conversation, ask their permission first and tell them what you plan to do with it. If they would rather not be recorded, a notebook works fine.

A short note after each conversation helps: the date, the questions you asked and two or three phrases they used. Even a few lines will be treasured later.

Fictional example

This short example is fictional and written only to show what an answer can look like.

Question: What was your first job, and what was your first day like?

“I was fifteen and I swept the floor of a bakery. I was so nervous that I arrived an hour early and stood outside in the cold. The baker laughed and gave me a warm roll. I think that is why I still love the smell of bread.”

You do not need a polished answer. A few honest sentences are already a good memory to keep.

If you’d like help

Some families love to sit at the kitchen table with a list. Others live far apart, or simply find it hard to find the time.

If it would help, Storykindly can send the questions by email. You choose a book and a start date. Your grandparent receives a question every two or three days and answers in writing on a private web page, with no account and no app. Each answer is lightly edited with AI from their own words, and they approve every chapter before it goes into the book. It arrives as a PDF.

It is a one-time payment, with no subscription. Your grandparent can say “No thanks” when they get the invitation, and you get a full refund. They can also skip a question or leave an answer out. A book is only made from what they choose to share.

See how Storykindly works

Whether you use a list, a notebook or questions by email, the most important part is the same: asking, and listening to what comes back.