If you've ever wondered what to ask your grandparents, and worried you might end up putting it off until it's too late, you’re not alone. So many people look back and realize they meant to ask about their life, but never quite knew where to begin.
This guide is here to change that.
Below, you'll find meaningful grandparent questions, family history interview questions, and practical guidance on how to record grandparents' stories in a way that allows them to be preserved for generations to come. Whether you're hoping for lighthearted memories or deeper conversations, this is a great place to begin.
What are the best questions to ask your grandparents?
The best questions to ask your grandparents focus on their life experiences, values, family history, and memories. Start with lighter questions, then move into deeper topics like relationships, challenges they overcame, and what they'd like future generations to know about them.
Examples of meaningful grandparent questions include:
- What was your childhood like?
- What moments shaped who you became?
- What values do you hope our family never loses?
- What do you want future generations to know about you?
Why Asking Your Grandparents Questions Matters (Now More Than Ever)
"I would give nearly anything to have one more conversation with them."
That's a common sentiment that many people share when they lose their grandparents before capturing their stories. It's a regret that shows up again and again: the realization that they had so many questions, but time quietly ran out.
If your grandparents are still alive, you have something incredibly valuable: time. And while it can feel unlimited, time with grandparents is anything but guaranteed. The questions you don't ask today often become the stories you never get to hear.
Asking your grandparents questions isn't just about preserving facts or dates. It's about understanding where you come from, as well as helping them feel seen in the process. For grandparents, sharing their life story can bring purpose, reduce isolation, and offer space to reflect on a life well lived.
These aren't just interviews. They're the kind of conversations that keep a family's story alive.
100+ Questions Organized by Conversation Style
The best questions don’t feel like an interview. They feel like a real conversation.
Below are over 100 meaningful grandparent questions, organized by conversation style and depth. You don't need to ask all of them. Pick a few, follow your curiosity, and let the conversation unfold naturally.
Icebreaker Questions (For Building Comfort)
Icebreaker questions help you ease into conversations with your grandparents.
These questions focus on childhood memories, everyday life, and familiar topics. They're ideal when you're not sure what to ask your grandparents, or for when you want to build comfort before asking deeper family history questions.
- What was your childhood home like?
- What games did you play as a kid?
- What was your favorite holiday growing up?
- What did you want to be when you were young?
- What was your first job?
- What was fashion like when you were a teenager?
- What was your favorite childhood meal?
- Did you have pets growing up?
- What was school like for you?
- What did you do for fun on weekends?
- What music did you listen to when you were young?
- What was dating like back then?
- Did you play sports or have hobbies?
- What was your neighborhood like?
- What feels most different about childhood today?
Life Journey & Personal History Questions
These questions go beneath the surface and into the decisions that shaped your grandparents' lives. This is the heart of many family history interview questions.
- How did you meet Grandma/Grandpa?
- What made you fall in love with them?
- Tell me about your wedding day.
- What was it like becoming a parent?
- How did you choose your career?
- What was the hardest decision you ever made?
- Was there a moment when your life could have gone a completely different direction?
- What challenge shaped you the most?
- When did you feel most proud of yourself?
- What historical events stand out most in your memory?
- Did you experience discrimination or unfair treatment?
- What was your relationship with your parents like?
- Were there family conflicts that shaped you?
- What do you wish you'd done differently?
- Who was your closest friend?
- What was the most adventurous thing you ever did?
- When did you feel uncertain about your future?
- What fear influenced you the most when you were younger?
- Tell me about a time you failed at something important.
- What sacrifice are you most proud of?
- When did you first feel like an adult?
- What's something people misunderstand about your generation?
- How did money challenges affect your life?
Wisdom & Values Questions
These questions invite reflection. They're less about what happened, and more about what it meant.
- What would you tell your 20-year-old self?
- What lesson did life teach you the hard way?
- What does a good life mean to you now?
- What regrets do you have—or not have?
- How do you define success?
- What values do you hope our family never loses?
- How has your understanding of love changed over time?
- What's the best advice you ever received?
- What advice do you give most often?
- How has your faith or spirituality evolved?
- What do you think happens after we die?
- What do you wish you'd spent more time on?
- What do you wish you'd worried less about?
- What makes a strong marriage or partnership?
- What makes someone a good parent?
- What are you most grateful for?
- What does happiness look like at this stage of your life?
- What truth took you the longest to learn?
- What character trait matters most to you?
- What belief did you hold when you were young that you no longer believe?
Legacy & Impact Questions
These questions focus on the deepest parts of their past, as well as what they'd like to pass down and how they'd like to be remembered.
- How do you want to be remembered?
- What do you hope people say about you?
- What traditions should our family keep alive?
- What values do you want passed down?
- What accomplishment are you most proud of?
- What impact do you hope you've had on others?
- What advice would you give the next generation?
- What family stories shouldn't be forgotten?
- What do you wish people understood about your life?
- What do you hope your children learned from you?
- What's the greatest gift you've given someone?
- Who do you think you influenced most?
- What would you want written on your tombstone?
- If you could leave one message for your family, what would it be?
- What should never be lost about our family history?
- Is there unfinished business you hope someone completes?
- How would you like your memory honored?
- What recipe, skill, or tradition must be preserved?
- What do you hope your legacy will be?
Memory & Nostalgia Questions
Nostalgia often unlocks the most heartfelt stories. These questions invite joy, reflection, and connection.
- What's your favorite memory with me?
- What was the happiest moment of your life?
- When did you feel most at peace?
- What's the funniest thing that ever happened to you?
- When did you feel most alive?
- What smell reminds you of childhood?
- What song takes you back in time?
- What's your favorite family memory?
- Describe a perfect day you remember.
- What place do you dream of returning to?
- What's the most beautiful thing you've ever seen?
- What holiday memory stands out most?
- Tell me about a time you laughed until you cried.
- What memory always makes you smile?
- What do you miss most about being young?
Fun & Unexpected Questions
Not all meaningful grandparent questions need to be serious. These can be humorous, and often reveal personality and spark laughter.
- If you could have a superpower, what would it be?
- If you could travel to any era, where would you go?
- What's the strangest food you've ever eaten?
- Who would you meet from history if you could?
- What's the most embarrassing moment of your life?
- What talent do you wish you had?
- What's your favorite movie or book?
- If you won the lottery tomorrow, what would you do?
- What's the weirdest dream you remember?
- If you could be famous for something, what would it be?
- What trend from your youth makes you laugh now?
- What would you love to learn instantly?
- What celebrity did you have a crush on?
- What's the best prank you ever pulled?
- What would you invent if you could?
Tips for Meaningful Grandparent Conversations
Great questions matter, but how you ask them matters even more.
Prepare, But Stay Flexible
Know the basics of their life, and pick a few questions ahead of time. Then let the conversation wander. The best stories are rarely planned.
Create the Right Environment
Choose a quiet, comfortable setting. Minimize distractions, and don’t rush. Give them time to think, as some stories take a moment to come back.
Listen More Than You Talk
Aim to listen far more than you speak. Ask open-ended questions, and let pauses happen. Curiosity is one of the most important things.
Record (With Permission)
If you're wondering how to record grandparents' stories, start simple. Ask permission, and explain why it matters to you. Even a basic voice memo preserves tone, emotion, and humor that text alone can't capture.
How to Record Grandparents' Stories
How do you record grandparents' stories?
To record your grandparents' stories, choose a quiet setting, ask permission, and keep the process simple. A phone voice memo or video recording is more than enough. Focus on open-ended questions, let pauses happen, and don't rush. Capturing their voice and memories authentically is far more important than having perfect production quality.
Common Questions About Talking With Your Grandparents
What if my grandparent doesn't like talking about the past?
If your grandparent doesn't like talking about the past, start with light, present-day topics and respect their boundaries. From there, you can try some of the fun questions about their life from the list above, going deeper if they feel comfortable.
How do I ask about difficult family topics?
If you want to ask about difficult family topics, ease into it and acknowledge that the subject may be sensitive. Make it clear that they do not need to share anything that feels uncomfortable, and allow them to decline without pressure.
What's the best way to preserve these stories?
The best way to preserve grandparents' stories is to record them using audio, video, or written transcripts and store them somewhere accessible. Recording them using your phone and saving them in the cloud is perfectly fine. The format matters less than making sure the stories are saved and shared.
Can meaningful conversations happen long-distance?
Absolutely! Meaningful conversations with grandparents can happen over the phone or via video chat. In fact, many people actually find it easier to share deeply when they're not in the same room as the person they're sharing with.
What if my grandparent has passed away?
If your grandparent has passed away, you can still learn about them and preserve their legacy by speaking with other family members and gathering stories, photos, and memories.
TL;DR - Questions to Ask Your Grandparents
Start with simple memories, ask open-ended questions, listen more than you talk, and record their stories when possible (with their permission). Focus on life lessons, family heritage, and legacy. And don't be too concerned about perfection. What matters most is showing up and preserving what you hear.
Turn These Conversations Into a Lasting Legacy Gift
You now know what questions to ask your grandparents, and how to ask them well. But meaningful conversations are eventually lost if they aren't preserved.
That's why we built Reminiscely.
Reminiscely helps families capture life stories through thoughtful weekly prompts. Stories can be shared by video or by writing them down - whichever feels most natural. Then when you're ready, we turn those memories into a beautiful hardcover book, complete with QR codes linking directly to the videos where you can watch them and hear their voice.
The questions are just the start. What matters most is the conversations that follow, and making sure those stories get saved.
Don't wait.