The 25 Questions That Will Unlock Your Family's Best Stories

You’ve set the date. You're going to sit down with your mom, your dad, or your grandparent to finally hear their stories. It’s an exciting—and slightly nerve-wracking—moment. You have your phone ready to record, you’ve poured two cups of tea, and then you’re faced with the most challenging question of all:

What do I actually ask?

The quality of a story often depends on the quality of the question. Simple questions get simple answers. "Where were you born?" will get you the name of a town. But a better question can unlock a universe.

The goal is to ask open-ended questions that invite memories, feelings, and details rather than just "yes" or "no" answers. We've gathered 25 of our favorite questions, broken down by life stage, to help you start a rich and meaningful conversation. You don't need to ask all of them; just pick a few that resonate with you and see where they lead.

Questions About Early Life & Childhood

The goal here is to explore their world before you were a part of it.

Beyond your city, what was the specific neighborhood or street you grew up on like? What did it sound or smell like?
What was your favorite game to play as a child? Who did you play it with?
Who was your best friend growing up, and what is one of your fondest memories with them?
What was a rule in your house that you always tried to break?
What is a meal that instantly reminds you of your childhood kitchen?

Questions About Young Adulthood & Career

This is about understanding their journey to becoming the person you know.

What was the very first job you ever had? What did it teach you?
What did you think you were going to be when you grew up, and how did that change over time?
Tell me about the day you met Mom/Dad/your partner. What was your first impression?
What was the biggest risk you took in your 20s? How did it turn out?
Describe the home where you first lived as an adult. What made it special?

Questions About Work, Passion & Skills

Explore what drove them and what they were proud of.

What was a skill you learned that you were particularly proud of, whether for work or a hobby?
Outside of work and family, what was something you were truly passionate about?
Can you describe a normal weekday for you when you were my age?
Who was a mentor or someone who had a big impact on your career, and what did you learn from them?
What was a major challenge you faced in your work life, and how did you overcome it?

Questions for Deeper Reflection

These questions go beyond events and into values, beliefs, and emotions.

What is a piece of advice your own parents gave you that has always stuck with you?
What is a tradition from your childhood that you were happy to pass on (or chose not to)?
Can you remember a time when you were genuinely surprised by how something in your life turned out?
What is a moment you felt truly happy and at peace? Where were you, and who were you with?
Looking back, what is something you wish you had known when you were younger?

The Five "Golden" Questions

If you only have time for a few, these are powerful questions that often lead to incredible stories.

What is one of the most rebellious things you ever did?
What is a story your own parents used to tell about their lives?
What are you most proud of in your life? (It doesn’t have to be a big achievement).
How would you like to be remembered?
Is there a story you've always wanted to tell but never got the chance?

A Final Tip: Listen More, Talk Less

The most important part of any interview is not the questions you ask, but how you listen to the answers. Let there be silence. Don't rush to the next question. Often, the best stories come after a thoughtful pause.

At Narrabel, our AI Historian is designed to help guide these conversations, but the magic truly comes from you and your family member sharing a moment. Pick a question, ask it with genuine curiosity, and get ready to listen. The story is already there, waiting to be told.