100 Questions to Ask Your Grandma (Printable List)

Your grandma has lived a life full of stories you've likely never heard—tales of her first love, the challenges she overcame, and the simple joys that defined her youth. But knowing how to ask about them can feel like the hardest part. This list of 100 questions to ask your grandma is a starting point for those conversations. It's a key to unlocking her memories, strengthening your bond, and preserving a legacy your family will cherish for generations by asking thoughtful questions about her life.

What you'll find here:

• Thoughtful questions organized by life stage and theme.
• Tips for making the conversation feel natural, not like an interrogation.
• Simple ways to record and cherish her stories for years to come.
• A simple way to connect in just five minutes.

Start Connecting in 5 Minutes

Feeling overwhelmed by the list? You don't need to ask all 100 questions at once. Here’s how to start a meaningful conversation in just a few minutes:

1. Scan the categories below and pick just 3 questions that genuinely spark your curiosity.
2. Find a relaxed moment, maybe over a cup of tea, and simply ask, "Grandma, I'd love to hear a story about..."

That's all it takes. The goal is connection, not a perfect interview. It all starts with a single, heartfelt question.

How to Have a Meaningful Conversation

This isn't about getting through a list of questions to ask grandma; it's about creating a warm, comfortable space for her to share. Here are a few tips for a meaningful conversation to help you turn these questions into a memorable chat.

Find the Right Time and Place

Choose a time when neither of you is rushed or distracted. A quiet afternoon on the porch, a cozy evening by the fire, or a calm morning in the kitchen can be perfect. Turn off the TV, put your phones away, and give her your full attention. This shows her that you truly value what she has to say.

Listen More Than You Talk

Your main role is to be a curious and loving listener. Ask a question, then let her story unfold. Resist the urge to interrupt or steer the conversation. Sometimes the most beautiful memories come from a moment of silence as she gathers her thoughts. Nods, smiles, and simple affirmations like "wow" or "really?" show you're engaged and encourage her to continue.

Ask Follow-Up Questions

An initial answer is often just the beginning of a great story. When she mentions a person, place, or event that piques your interest, gently probe for more details.

• "What did that feel like?"
• "Who else was there?"
• "Tell me more about that."
• "Why do you think that happened?"

These simple follow-ups can turn a one-sentence answer into a rich, detailed narrative.

Be Prepared for Sensitive Topics

Not all memories are happy ones. Some questions might bring up difficult memories of loss, hardship, or regret. If she gets emotional or seems hesitant, that's okay. Offer a comforting hand, acknowledge the feeling ("That sounds like it was really hard"), and let her know it's perfectly fine to skip a question. The goal is to connect, not to cause distress.

100 Questions to Ask Your Grandma

Here is a comprehensive list of questions, broken down by theme. Remember to pick and choose the ones that feel right for you and your grandma.

Questions About Her Childhood & Youth

1. What is your earliest memory?
2. Where did you grow up? What was your house like?
3. What were your parents like?
4. Did you have any nicknames growing up?
5. What was your favorite game to play as a child?
6. Who was your best friend, and what did you do together?
7. What kind of trouble did you get into as a kid?
8. What was your favorite subject in school? Your least favorite?
9. What did you want to be when you grew up?
10. What were holidays like for your family? Any special traditions?
11. What chores did you have to do around the house?
12. What was a typical family dinner like?
13. How did your family listen to music or news? (Radio, records?)
14. What world events had the biggest impact on you as a child?
15. What was your relationship with your siblings like?
16. Did you have a favorite toy or possession?
17. What's a smell that takes you right back to your childhood?
18. What was the best home-cooked meal your mother made?
19. Did you have any pets?
20. What is something you did as a child that kids today would never do?

Questions About Love, Marriage & Family

1. How did you meet Grandpa? What was your first impression? (If you're looking for more, here are some great questions to ask your grandpa, too!) 22. What was your first date like?
2. How did he propose?
3. Tell me about your wedding day. What was your favorite memory from it?
4. What was the best marriage advice you ever received?
5. What was the hardest part about being a young wife and mother?
6. What were you like as a new parent?
7. What is your favorite memory of raising my mom/dad?
8. What was my mom/dad like as a child?
9. How did you choose your children's names?
10. What family tradition are you most proud of?
11. What do you think is the secret to a long, happy marriage?
12. What was the most romantic thing Grandpa ever did for you?
13. How has the meaning of love changed for you over your lifetime?
14. What was the biggest challenge you faced as a couple?
15. What is a favorite family vacation you took?
16. How did you feel when you became a grandmother for the first time?
17. What is one thing you hope your grandchildren learn from your marriage?
18. What did you and Grandpa do for fun when you were first married?
19. What quality do you admire most about your spouse?

Questions About Her Career & Life Experiences

1. What was your first job? How much did you get paid?
2. What was the most interesting job you ever had?
3. Did you face any challenges as a woman in the workforce?
4. If you could have had any other career, what would it have been?
5. What was the biggest risk you ever took in your life?
6. Have you ever traveled to another country? What was it like?
7. What historical event during your life had the most significant impact on you?
8. What was it like to live through [a specific event, e.g., WWII, the Moon landing, the Civil Rights Movement]?
9. What invention has changed your life the most?
10. What was the hardest thing you ever had to learn to do?
11. Have you ever been in a natural disaster?
12. What was the most beautiful place you've ever visited?
13. Did you have a mentor who influenced you?
14. What skills did you learn that have been most useful in your life?
15. How did you spend your free time in your 20s and 30s?
16. What's a piece of technology from your youth you wish still existed?
17. What's a piece of modern technology you can't live without?
18. Have you ever met anyone famous?
19. What was the biggest news story you remember from your younger years?
20. What's a fashion trend you followed that you laugh about now?

Questions About Life Lessons & Wisdom

1. What are you most proud of in your life?
2. What is one of your biggest regrets?
3. What is the most important lesson life has taught you?
4. If you could give your 20-year-old self one piece of advice, what would it be?
5. What does "success" mean to you?
6. What do you value most in a friendship?
7. How has your perspective on life changed as you've gotten older?
8. What's something you know now that you wish you'd known when you were younger?
9. What is the best advice your own mother or grandmother ever gave you?
10. What are you most grateful for?
11. What do you think is the key to happiness?
12. How do you want to be remembered?
13. What's a mistake you made that taught you a valuable lesson?
14. What is your definition of a "good life"?
15. What is the hardest thing you've ever had to forgive?
16. What do you worry about most now?
17. What brings you the most joy these days?
18. What is a small thing that makes you happy?
19. What piece of advice would you give to new parents?
20. What do you think your greatest strength is?

Fun & Lighthearted Questions

1. What's the funniest thing that's ever happened to you?
2. What was your favorite movie when you were a teenager?
3. Who was your favorite singer or band?
4. What's a secret family recipe you can share with me?
5. What's the most mischievous thing you did as a teenager?
6. If you could have dinner with three people, living or dead, who would they be?
7. What was the worst haircut you ever had?
8. What's a food you could never get tired of?
9. Do you have any hidden talents?
10. What's something people would be surprised to learn about you?
11. What was your favorite car you ever owned?
12. What's the best gift you've ever received?
13. What's your favorite joke?
14. If you had a superpower, what would it be?
15. What's your favorite season and why?
16. Are you a morning person or a night owl?
17. What's a simple pleasure you enjoy every day?
18. What's your favorite board game or card game?
19. What's the craziest fashion you ever wore?
20. If our family had a motto, what would it be?

How to Preserve These Precious Memories

Once you've shared these moments, you'll want to hold onto them. Here are a few simple ways to preserve these memories for yourself and for future generations.

Use a Voice Recorder App

The easiest way to capture every word, laugh, and pause is to record the conversation. Your smartphone’s voice memo app is perfect for this. Just be sure to ask for her permission first. Simply say, "Would you mind if I recorded this? I don't want to forget any of your amazing stories."

Take Notes in a Journal

If recording feels too formal, a simple notebook is a great alternative. You don't have to write down every word. Instead, focus on capturing:

• Key dates, names, and places.
• Direct quotes that capture her personality.
• The emotions and feelings behind the stories.

Create a Family Storybook

Turn her answers into a beautiful book. You can transcribe the recordings, pair her stories with old family photos, and organize everything by chapters (e.g., "Childhood," "Our Family"). This can become a priceless family heirloom. For an easy way to compare options, see our Abrevity vs Remento guide.

Scan Old Photos as You Talk

Bring out old photo albums before you start. Looking at pictures is one of the best ways to jog memories. As she tells a story about a particular photo, use a phone app like Google PhotoScan to create a digital copy right then and there. You can add notes to the digital file about who is in the photo and the story behind it.

For more inspiration on connecting with loved ones, check out our other lists of questions to ask.