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November 16, 2022


Spark Heartfelt Family Conversations Over the Holidays—and Beyond

One of the hallmarks of the holiday season is sitting down and spending quality time with family. It’s a time to hear familiar stories from your favorite uncle, shush Mom as she shares embarrassing memories from your childhood, or make funny faces across the dinner table at a little one. But most importantly, the holidays are an opportunity to meaningfully connect, as the busyness of everyday life yields to the magic of this special season.

This year, why not use your holiday gathering to learn more about each other—to ask questions you haven’t asked before, or to explore new understandings of stories you know well? To help, we’ve gathered prompts from our family keepsakes that you can use as thoughtful conversation starters.

Choose a question for everyone to answer as you sit down for your holiday meal. Or have each person select different questions you can discuss after opening gifts. However you engage, we hope these conversation prompts help deepen your bond and celebrate the legacy you are building together.


  • What is your favorite holiday to celebrate?
  • As a child, what were some holiday traditions that you had?
  • What memorable gifts (big or small) have you received?


  • What do you miss most about being a kid? It can be a specific activity or perhaps a feeling you miss.
  • What rules did your parents have, and which ones did you test the most?
  • What are some of your childhood nicknames and where did they come from?


  • What is your favorite quote or saying?
  • What is something you are proud of?
  • Who are some people you admire and why? These could be lifelong friends, celebrities, family members, etc.


  • What are some things you have yet to do and would like to accomplish in your lifetime?
  • What interesting places have you visited? What made them so memorable?
  • What about you has stayed the same throughout your life? What’s changed?


Continue the conversation beyond the holidays with the prompts inside our family keepsake books. Whether you are looking to record the words and wisdom of a parent, grandparent, or another beloved elder, you’ll find wonderful ways to preserve their lessons and legacy.

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