150 Family History Interview Questions (By Life Stage)
The biggest regret after losing someone? Not asking enough questions.
Stories slip away faster than we think — and the best way to preserve them is by asking thoughtful, open-ended questions. To make it easy, we’ve created a list of 150 prompts, organized by life stage.
Whether you’re recording an oral history or just starting a dinner-table conversation, these questions spark stories worth keeping.
Childhood & Family Home
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What’s your earliest memory?
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Who was your best friend as a child?
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What did your childhood home look like?
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Did you have pets?
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What family traditions did you grow up with?
School Days
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Who was your favorite teacher?
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What subjects did you enjoy most?
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How did you get to school?
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Did you ever get into trouble?
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What was your first job as a teenager?
Love & Relationships
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How did you meet your partner?
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What was your first date like?
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How did you propose (or get proposed to)?
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What was your wedding day like?
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What’s your secret to a lasting relationship?
Work & Purpose
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What was your first full-time job?
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What was your proudest career moment?
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Did you ever dream of doing something else?
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Did you have a mentor who influenced you?
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What’s the hardest lesson you learned at work?
Major Life Events
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Where were you when a big world event happened (moon landing, 9/11)?
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How did those events change your life?
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What was your proudest personal achievement?
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Did you ever move to a new country or city?
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What was the most challenging decision you’ve made?
Parenting & Family Wisdom
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What was it like raising children?
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Did you have a bedtime story or lullaby?
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What’s the funniest parenting moment you remember?
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What’s the best advice you’d give new parents today?
Life Lessons & Reflections
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What advice would you give your younger self?
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What’s the hardest challenge you’ve overcome?
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What’s your biggest success in life?
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What makes a happy life?
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What message would you like future generations to remember?
Everyday Joys
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What music did you love to dance to?
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What was your favorite meal growing up?
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Did you ever go on a memorable holiday?
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What hobbies or pastimes made you happiest?
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What’s the best joke you’ve ever told?
Rapid-Fire Fun Questions
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Tea or coffee?
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Morning person or night owl?
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Sweet or savory?
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What’s a song you’ll always sing along to?
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Who was your childhood hero?
How to Use These Questions
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Pick a few at a time. Don’t overwhelm the conversation.
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Record the answers. Even short clips become treasures.
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Follow up. Ask “why” and “what happened next” to go deeper.
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Make it a ritual. Ask one question every holiday or birthday.
Why These Questions Matter
Every question is an invitation — to be seen, to be remembered, to be connected. The stories you capture become the threads that hold generations together.
Final Thought
Don’t wait. Even 10 minutes of questions today can become an heirloom tomorrow.
Chaptr was built to make preserving stories effortless. Join as a Founder Member and help us create the ultimate family storytelling tool.