Your grandparents carry memories that may not make it into history books but are invaluable to you and your family. They remember everyday moments, family traditions, and personal experiences that shaped your family’s story. Those stories don't last forever, which makes it important to ask the right questions while you still can. This guide includes 100+ questions to ask your grandparents, organized by life stage and theme. You will find prompts about childhood, love, work, history, and life lessons. Whether you are having a casual conversation, recording stories, or gathering memories for a book, these questions help turn conversations into lasting family history.

TLDR:

• Asking thoughtful questions preserves irreplaceable family stories before they’re lost
• 100+ questions to cover childhood, love, career, history, and life wisdom
• Recording conversations captures authentic voices and laughter for future generations
• Storyworth emails one question weekly and compiles the answers into a hardcover keepsake book

Why Asking Your Grandparents Questions Matters

Grandparents are living archives of family history, cultural change, and personal experience. Many people assume there will always be more time to ask questions, but nearly 40% of adults over 65 experience some level of memory decline.

Although 61% of Americans say they learned family history from their grandparents, most of that knowledge comes from casual conversations that were never recorded. Asking specific, intentional questions helps move beyond small talk and captures your grandparents’ stories in their own words.

Many families choose to collect these stories gradually, using services like Storyworth to keep the process manageable and straightforward. By sending one question at a time and allowing grandparents to respond in ways that feel comfortable, families can focus on listening and remembering versus managing technology.

Childhood and Early Life Questions

The years before your grandparents became adults often hold the most surprising stories. These are good questions to ask your grandparents about their childhood, focusing on the details of their earliest days.

• What is one of your earliest childhood memories?
• What is one of your fondest childhood memories?
• What games or toys did you enjoy most when you were young?
• Did you have any nicknames when you were a child? How did you feel about them?
• What was your favorite candy as a child?
• Who had the most positive influence on you as a child?
• Were you ever teased about anything as a child?
• Did you ever move as a child? What was that experience like?
• What fascinated you as a child?
• What was your weekend tradition when you were a kid?

Questions About Their Parents and Ancestors

Your grandparents hold the keys to understanding earlier generations. Asking your grandparents questions about family history turns names on a family tree into real people with real stories. These prompts uncover your roots and help you develop a list of questions you might wish you could ask your great-grandparents, preserving origins before those memories fade.

• What were your parents’ relationship like?
• Did you have any particularly vivid memories of your grandparents?
• How far back can you trace your family ancestry?
• What did your parents or grandparents do for a living?
• Are there any stories about how our ancestors came to this country?
• What are the most important lessons you learned from your parents?
• Do you remember any stories your grandparents told you about their youth?
• In what ways are you more like your mother? How are you more like your father?
• Are there any physical traits that have been passed down through generations?
• Do you have a family member you wish you’d gotten to know better?

Questions About Love, Marriage, and Relationships

Romance often looked very different in earlier decades. Asking about courtship gives you a glimpse into your grandparents’ hearts and the origins of your family tree. These questions about love and marriage help uncover the early spark of their relationship, whether they met at a dance, at church, or through handwritten letters.

• How did you meet your spouse or partner?
• What was your first impression of your spouse or partner?
• What was your first date like with your spouse or partner?
• What was your proposal like?
• What was your wedding like?
• Where did you go on your honeymoon?
• What is one of your favorite memories with your spouse or partner?
• What was one of the most difficult times in your relationship? How did you get through it?
• What do you think is key to maintaining a happy relationship?
• What qualities do you most value in your spouse or partner?

Career and Work Life Questions

Workplaces and career paths have changed dramatically over the decades. Asking about your grandparents’ professional lives helps you understand the effort and sacrifice that contributed to your family’s stability. These questions range from their first paychecks to the achievements they are proudest of.

• What job(s) did you have when you were in high school?
• How did you get your first job?
• Did you consider any careers other than the one where you landed?
• Who was your best boss like? What did you learn from them?
• What was the hardest job you ever had?
• How did you decide when to change jobs?
• Did you ever serve in the military?
• What are some of your biggest professional accomplishments?
• What were you like when you were 30?
• If you had to go back in time and start a brand new career, what would it be?

Questions About Historical Events They Witnessed

Asking your grandparents questions about history turns textbook dates into personal memories. Hearing where they were during major events, or how those moments affected everyday life, gives you a deeper sense of both your family’s story and the world they helped shape.

• What’s the first major news story you can remember living through as a child?
• Where were you during the moon landing?
• How is life different today compared to when you were a child?
• Did your family participate in the Civil Rights Movement?
• Where were you when you found out that JFK had been assassinated? How did it affect you?
• How did a major war affect your community or family?
• How has the country changed during your lifetime?
• Which U.S. President did you admire most?
• What was the biggest scandal you remember seeing in the news?
• Do you think the world is better today than when you were growing up?

Family Traditions and Cultural Heritage Questions

Family traditions often live in small details like handwritten recipes, holiday rituals, familiar songs, or objects passed down through generations. These are the kinds of memories that are easy to overlook unless they are intentionally captured. This is also where having a flexible storytelling format helps. Services like Storyworth allow families to collect written stories, photos, and audio responses without requiring grandparents to learn new technology or use a smartphone.

• What traditions do you keep that are related to your family’s heritage?
• Is there a specific family recipe that has been passed down?
• Did your family speak a language other than English at home?
• What foods were served at weddings or special occasions?
• What keepsakes or family heirlooms do you treasure most?
• What religious customs were important to your parents?
• How did you celebrate birthdays growing up?
• What are you superstitious about?
• What music was always played at family gatherings?
• What are some of the most memorable gatherings or reunions with your extended family?

Life Lessons and Advice Questions

Experience brings a perspective only time can provide. Asking your grandparents for advice lets you benefit from their hard-earned wisdom and understand the values they hope will continue in your family.

• What are the most important lessons you’ve learned in life?
• If you could hold on to just one memory forever, what would it be?
• What advice would you give your 20-year-old self?
• What do you think is the meaning of life?
• How did you get through unhappy times in your life?
• What do you worry about?
• What do you consider true success?
• What values matter most to you?
• What’s a small decision you made that had a big impact on your life?
• How do you want to be remembered?

Questions About Everyday Life in Their Era

Younger generations often struggle to imagine a world without smartphones, microwaves, or streaming services. Asking your grandparents questions about daily life brings those details into focus. For grandparents who prefer speaking, Storyworth offers the option to record answers by phone, including through a landline. They can request a callback and talk, making it easier to capture stories without needing a computer or internet connection.

• What was your first car?
• How much did things like gas or groceries cost when you were young?
• Did your family have a television growing up? What shows did you watch?
• How did you listen to music before cassette tapes or CDs existed?
• What was your favorite fashion trend as a teenager?
• Did you ever have a party line on your telephone?
• How did you stay cool in the summer before air conditioning was common?
• Where did your family go grocery shopping?
• What chores did you have as a child?
• How did you stay in touch with friends who lived far away?

Questions About Their Proudest Moments and Achievements

We often focus on dates and timelines, but emotional high points tell you who someone really is. Asking your grandparents questions about their lives lets them revisit moments of courage, perseverance, and joy. Stories of resilience often become the chapters families return to most when looking back.

• What things are you proudest of in your life?
• What is one of the bravest things you’ve ever done?
• What stands out as one of your most meaningful projects?
• When did you feel the most independent?
• What special talents are you most proud of?
• What is one of the best decisions you made for your family?
• Have you ever had to stand up for your principles?
• What’s a small victory that meant a lot to you?
• What contribution to your community are you most proud of?
• What brings you the most pride when you look at your family today?

Funny and Lighthearted Questions

Capturing laughter matters just as much as preserving wisdom. Funny questions often lead to the stories families end up retelling for years. These prompts showcase their playful side and make conversations feel relaxed and fun.

• Did you ever get a terrible haircut?
• Did you ever try to sneak out of the house?
• What’s something funny you believed as a child?
• Who was one of your first crushes?
• What’s a funny or embarrassing story your family tells about you?
• Have you ever played a prank that went wrong?
• What was the biggest kitchen disaster you ever experienced?
• Did you ever get in trouble at school for something silly?
• What’s the strangest gift you’ve ever received?
• What’s one food you love that most people don’t?

Deep and Meaningful Questions About Life and Legacy

At Storyworth, we believe meaningful conversations strengthen family bonds. Asking deep questions invites your grandparents to share how they see the world, what happened, and what it meant to them. These prompts dig into how their beliefs have evolved and what they hope future generations remember.

• How has your definition of happiness changed over time?
• What belief did you once hold strongly that you later changed your mind about?
• Do you believe in a higher power?
• Is there anyone you wish you had forgiven sooner?
• What do you hope your great-grandchildren remember about you?
• What was the hardest goodbye you ever had to say?
• Do you believe people shape their own destiny?
• What are you most grateful for right now?
• If you could relive one decade of your life, which would it be?
• What’s the single most important thing you want your family to remember?

How to Conduct a Meaningful Interview With Your Grandparents

The setting and approach you choose can shape how comfortable these conversations feel. A relaxed pace, thoughtful prompts, and the ability to focus on listening often lead to better stories. Recording conversations can help preserve voices and details without turning the moment into an interview. Storyworth supports this by offering audio recording and automatic transcription, so stories can be saved accurately while you stay present in the conversation.

Capture the Audio

If you can, record the conversation so you can focus on listening instead of taking notes. This preserves their exact voice and laughter, making it easier to create a question to ask your grandparents later. With Storyworth, storytellers can even request a phone call and simply speak their answers while the service records and transcribes them, so they do not need a computer or smartphone.

Go Beyond the Script

Treat these interview questions and answers as a starting point, not a rigid checklist. Follow-up questions and side stories often reveal the most personal family history and are the moments your relatives will remember most.

Preserving Your Grandparents' Stories With Storyworth

Collecting a lifetime of stories does not have to happen all at once. Storyworth breaks the process into small, meaningful steps by sending one thoughtful question each week. Grandparents can respond by email, write their stories directly on our site, or voice record over the phone.

For storytellers who find typing difficult, phone recording allows them to tell their stories over the phone (even a landline) in their own words. Storytellers can request a phone call from Storyworth and their story will automatically be transcribed into their memoir in their own words.

At the end of the year, we compile every story along with unlimited photos into a beautiful hardcover book, creating a lasting heirloom your family can pass down for generations.

Final Thoughts on Asking Your Grandparents the Right Questions

Researching fun questions to ask your grandparents is less about checking off a list and more about creating space for stories to surface. You do not need to capture everything at once. A few intentionally asked questions, consistently over time, are often enough to preserve memories that would otherwise fade.

FAQs

How many questions should I ask my grandparents in one sitting?

Start with just a few questions per conversation so it feels comfortable and relaxed. Recording one story at a time lets your grandparents share details without feeling rushed, and you can always schedule another call or visit to continue.

What's the best way to record my grandparents' answers to these questions?

You can use your phone’s voice recorder, jot down notes during the conversation, or use a service like Storyworth that emails one question per week and automatically saves written or phone-recorded responses. Recording audio captures their exact voice and laughter, which adds warmth when you revisit the stories or print them in a keepsake book.

Should I ask serious questions or funny questions first?

Begin with light-hearted topics such as childhood games, favorite foods, or funny memories to help your grandparents relax and start talking. Once they’re comfortable, you can naturally move into deeper questions about life lessons or historical events they witnessed.

How do I get my grandparents to share stories if they say they don't remember much?

Instead of broad prompts like “Tell me about your childhood,” try very specific questions about sensory details, what their kitchen smelled like, what songs played at family gatherings, or what the movie theater looked like. Concrete prompts often unlock vivid memories that seemed forgotten at first.

Can I turn my grandparents' answers into a printed book?

Yes. Storyworth makes it easy to collect your grandparents’ stories and photos throughout the year and print them all in a hardcover memoir book that looks like it came from a bookstore. Their Storyworth Memoir becomes a keepsake your whole family can treasure and share with future generations.