Three Questions to Uncover Your Grandparents’ Untold Stories

(A Gentle Guide to Start the Conversation)

Our grandparents hold a kind of wisdom that can’t be found in books. Their stories are pieces of living history, full of lessons, laughter, and experiences that shaped not only their lives, but ours.

Yet, for many families, those stories go untold. Life gets busy, visits are short, and it can feel awkward to start those deeper conversations. But once you ask the right questions, something magical happens, their eyes light up, memories awaken, and you realize you’re hearing stories no one else ever has.

You don’t need a perfect setup or hours of interview time to begin. Sometimes, all it takes is one thoughtful question to open the door.

Here are three simple, heartfelt questions that can help uncover your grandparents’ untold stories and start meaningful conversations you’ll cherish forever.

1. “What was life like when you were my age?”

This question instantly builds a bridge between generations. It takes something familiar, your current stage of life, and invites them to step back into their own memory of that time.

Maybe your grandfather will tell you about walking to school in the rain, or your grandmother will share how she first learned to cook from her mother. You might hear about what things cost back then, what music was playing on the radio, or what dreams they had for their future.

You’ll notice their expressions change as they remember, their voice softens, their hands start to gesture, and suddenly, the past feels alive again.

It’s a question that brings perspective, too. You begin to see the thread that connects your life to theirs, how the world has changed, and how, in many ways, it hasn’t.

2. “What is one lesson or piece of advice you hope our family remembers?”

This question gives them the space to pass down values, not just stories.
It shifts the conversation from memory to meaning.

You may hear something simple, like “Always be kind,” or something deeply personal, like “Don’t let fear stop you from doing what you love.” These moments often bring tears, laughter, and gratitude, because you realize you’re receiving something priceless: their wisdom in their own words.

Sometimes, the answer to this question becomes a defining part of a family legacy. It’s the kind of message that gets written down, quoted, or replayed for generations to come.

If you record their response, even just a short clip, you’ll have something truly special. Imagine being able to share your grandmother’s voice saying, “Don’t give up on love,” or your grandfather’s words of encouragement during hard times. Those recordings become anchors of comfort and connection for years ahead.

3. “What are you most proud of in your life?”

This question opens the heart. It gives your grandparents a chance to reflect on what truly mattered most, not just accomplishments, but moments of courage, kindness, and growth.

Their answers might surprise you. Sometimes pride isn’t tied to big achievements, but to small, meaningful victories: raising a family, staying married through challenges, starting over after loss, or simply living with integrity.

When they tell you what they’re proud of, you’re hearing what defined them. It’s one of the most beautiful ways to understand the story behind who they became, and, in turn, a piece of who you are.

Start Now, Don’t Wait for the “Right” Time

The truth is, there’s no perfect moment to ask these questions.
You can start during a casual visit, a phone call, or even while flipping through old photos together. The key is to listen with your heart.

Don’t worry about making it formal, let it flow naturally. One story leads to another, and soon you’ll find yourselves laughing, reminiscing, and maybe even uncovering stories you never knew existed.

And if your grandparents have boxes of photos tucked away, this is also a wonderful time to bring them out. While you talk, consider scanning and preserving those images.  If you don't have the ability to scan, our Legacy Photo Digitizing Service is a service we offer, so those moments are never lost.

It’s a small step that protects decades of family history, and gives you the opportunity to pair those voices and memories with the images that tell the rest of the story.

A Final Thought

Every grandparent has stories waiting to be heard, and every family has a storyteller waiting to ask.

These three questions are just the beginning, but they open the door to something that will outlast us all: a legacy of love, laughter, and life lessons that generations will hold dear.  Consider giving Grandma or Grandpa the gift of a Legacy Life Story Interview to have a more in-depth account of your loved ones life!

Don’t wait. Ask today. Record what you can.
Because someday, those words, spoken in their own voice, will be the most treasured gift your family has. 💛