Your grandpa is a living library, full of stories, wisdom, and memories you can’t find anywhere else. But knowing where to start can feel daunting. This list of 100 questions to ask your grandpa is designed to help you gently unlock those stories. Think of these prompts as easy conversation starters for grandparents, turning a simple chat into a memory you'll both cherish.
What you'll learn:
We help with tailored questions that fit your situation. See how it works.
- Simple tips to make the conversation feel natural and fun.
- 100+ thoughtful questions organized by life stage and theme.
- Easy ways to record and preserve his stories for years to come.
Start This Conversation in 5 Minutes
Feeling overwhelmed by the full list? Don't be. A real connection starts with a single question.
- Choose just 3 questions from the 'Childhood' section below. Pick ones you're genuinely curious about.
- Find a relaxed moment and say, "Grandpa, I was thinking about you and would love to hear a story about when you were a kid..."
Before You Ask: Tips for a Great Conversation
The goal isn't just to get answers; it's to connect. The last thing you want is for this to feel like an interrogation. Here’s how to keep the conversation relaxed, fun, and meaningful.
Make it a conversation, not an interview
Share your own experiences, too. If he talks about his first car, mention yours. This makes it a two-way street. The goal is to connect, not just to interview your grandfather. This isn't a deposition; it's a chat between family, helping him feel more comfortable opening up.
Choose the right time and place
Don't spring this on him during a chaotic family holiday dinner. Find a quiet time when neither of you is rushed. A lazy afternoon on the porch, a long car ride, or a quiet cup of coffee together can be the perfect setting.
Use photos and objects as prompts
Old photo albums are storytelling goldmines. Pull one out and ask, "Who is this?" or "Where was this taken?" Heirlooms, old report cards, or even a favorite tool from his workshop can trigger incredible memories.
Listen more than you talk
Your main job is to listen with genuine curiosity. Ask follow-up questions like, "What was that like?" or "How did that make you feel?" Let him pause and think. Sometimes the best stories come after a moment of silence.
It's okay to go off-topic
The list is a guide, not a script. If a question about his first job leads to a 20-minute story about a road trip he took that summer, let it happen. That's where the magic is. The most memorable tales are often the ones you never planned to hear.
What you'll need:
- A notepad and pen (or a laptop)
- A phone with a voice memo app (ask for permission first!)
- A few old family photos to get the ball rolling
Questions About His Childhood & Early Life
These questions for grandpa help paint a picture of the world he grew up in and the person he was becoming.
- What is your earliest memory?
- Where did you grow up? What was your home like?
- What were your parents like? What’s a favorite memory you have of them?
- Did you have any siblings? What was your relationship with them like?
- What was your favorite game to play as a child?
- Who was your best friend growing up? Are you still in touch?
- What kind of trouble did you get into as a kid?
- What was school like for you? What were your favorite and least favorite subjects?
- Did you have any chores? What were they?
- What was the biggest news event you remember from your childhood?
- What did you want to be when you grew up?
- What was a typical family dinner like at your house?
- Did you have any pets?
- How did your family celebrate holidays or birthdays?
- What’s a favorite meal your mom or dad used to make?
- What was your most prized possession as a child?
- Did you play any sports?
- What was the best piece of advice you ever got from your parents?
- What did you do for fun on the weekends?
- Looking back, what do you miss most about being a kid?
Questions About Love, Family, & Friends
Explore the relationships that shaped his life, from his first crush to becoming a father and grandfather himself. (And if you're looking for more, here are some questions to ask your grandma, or you can browse all our lists of questions to ask.) 21. How did you meet Grandma? What was your first date?
- When did you know you wanted to marry her?
- What was your wedding day like?
- What’s the secret to a long and happy marriage?
- What was it like becoming a father for the first time?
- What’s one of your favorite memories of raising my mom/dad?
- What were my parents like as teenagers?
- How did you feel when you found out you were going to be a grandfather?
- What do you admire most about your children?
- Who has been the most influential person in your life?
- Can you tell me about your best friends through the years?
- What’s the biggest fight you ever had with a friend?
- What qualities do you value most in a friendship?
- What was your first heartbreak like?
- How has the definition of "family" changed for you over your lifetime?
- What family traditions are most important to you?
- What’s a story about our family that you think I should know?
- What do you think is the most important thing for a family to do together?
- What are you most proud of in our family?
- What advice would you give to new parents today?
Questions About His Career & Work Life
From his very first job to his retirement, his career holds lessons about passion, hard work, and finding your way.
- What was your very first paying job?
- What was the worst job you ever had?
- What career path did you choose? Did you always know you wanted to do that?
- What was the biggest challenge you faced in your career?
- What accomplishment at work are you most proud of?
- Did you have a mentor? What did they teach you?
- How did you handle work-life balance when your kids were young?
- What was the most valuable lesson you learned from a boss or coworker?
- If you could do it all over again, would you choose the same career?
- What skills were most important for your job?
- How has the world of work changed since you started?
- What was your favorite part of your job?
- Did you ever have to make a really difficult decision at work?
- What was your daily routine like when you were working?
- How did it feel to retire?
- What’s the best career advice you could give me?
- Did you ever start your own business or think about it?
- What was the biggest risk you ever took in your career?
- Who did you admire professionally?
- What did you do with your first real paycheck?
Questions About Life Lessons & Wisdom
These questions tap into the incredible perspective that only comes from a life fully lived.
- What are you most proud of in your life?
- What’s one thing you wish you had done differently?
- What has been the happiest moment of your life so far?
- What was the hardest time in your life, and how did you get through it?
- What’s the biggest risk you’ve ever taken? Was it worth it?
- What does "success" mean to you?
- What are you most grateful for?
- If you could give your 20-year-old self one piece of advice, what would it be?
- What have you learned about happiness?
- What’s something you thought was important when you were younger that isn’t anymore?
- How has the world changed for the better since you were young? For the worse?
- What historical event had the biggest impact on your life?
- What do you think your legacy will be?
- What’s one belief you hold that you’ll never change?
- What is the most important lesson life has taught you?
- How do you deal with fear or worry?
- What do you wish you had spent more time doing?
- What’s a mistake you made that taught you a valuable lesson?
- What do you hope for the future of our family?
- In your opinion, what is the key to a good life?
Fun & Lighthearted Questions
Don’t forget the silly stuff! These questions can lead to some of the funniest and most surprising stories.
- What was the best concert you ever went to?
- What was the first movie you remember seeing in a theater?
- What’s the most beautiful place you’ve ever visited?
- If you could have any superpower, what would it be?
- What was your first car?
- What’s the silliest thing you’ve ever done?
- What music did you listen to as a teenager?
- What’s a food you could eat every day?
- Are you a dog person or a cat person?
- What’s the best practical joke you ever pulled?
- If you could have dinner with any three people, living or dead, who would they be?
- What was the most fashionable (or unfashionable) thing you ever wore?
- What’s your favorite joke?
- What’s a skill you have that might surprise people?
- What’s your favorite sports team?
- What’s the best gift you’ve ever received?
- What’s your favorite thing to do on a lazy Sunday?
- If you won the lottery, what’s the first thing you would buy?
- What’s a simple pleasure that always makes you happy?
- Of all the things I could ask you, what do you wish I would ask?
We help with tailored questions that fit your situation. See how it works.
We help with tailored questions that fit your situation. See how it works.
How to Record and Preserve His Stories
Once the stories start flowing, you’ll want a simple way to hang on to them. You don't need fancy equipment; the best method is the one you'll actually use. For more detailed ideas, check out our guide on preserving your family's history.
Use a voice memo app on your phone
This is the easiest way to capture every detail in his own voice. Just ask, "Grandpa, would you mind if I recorded this so I don't forget it?" Place the phone on a table between you and hit record.
Take notes in a dedicated journal
A simple notebook allows you to jot down key dates, names, and quotes. It feels less intrusive than a phone and can become a treasured keepsake itself.
Create a simple video recording
If your grandpa is comfortable with it, propping up your phone to record a video can be wonderful. Capturing his facial expressions and gestures as he tells a story adds a whole new layer to the memory.
Turn stories into a photo book
After your conversations, you can pair his best quotes and stories with old photos. Services like Shutterfly or Mixbook make it easy to create a beautiful "Story of Grandpa" book that the whole family can enjoy.
Once you've gathered these precious memories, you might wonder how to weave them into a clear story your family will treasure for years to come. Organizing everything into a cohesive narrative can feel like a big project, but it's a deeply rewarding one.