Holiday Table Talk - Questions That Spark Stories Across Generations
It’s the time of year when family and friends gather around a table piled high with favorite foods — and sometimes fraught conversations. The stories shared in these moments often become the memories we cherish most, and they can even spark reflections on the legacy we want to leave. If politics and religion are off the table, try these questions to get dialogue flowing across generations at your holiday meal.
Tuck them under plates, scatter them as table decorations, or come up with your own creative way to spark conversation.
Silly Starter Questions
What’s the strangest dream you’ve ever had?
If you could only eat one food for the rest of your life, what would it be?
What’s a life-changing purchase you’ve made?
What’s your go-to karaoke song? Or what would be your life theme song?
If you could make up your own holiday, what would it be, and how would it be celebrated?
Memory Lane Questions
What’s a memorable family vacation you took when you were a kid?
Of the previous houses you’ve lived in, which one did you like the most and why?
What’s a holiday tradition your family had that others might consider unusual?
What was your favorite Halloween costume as a kid?
What did you want to be when you grew up? How has that changed?
Life Lesson Questions
What’s an important lesson you wish you’d learned sooner in life?
What’s the best advice you’ve ever been given? It can be serious or light-hearted.
What’s one thing you’d like to learn to do well?
If you could travel back to talk to your younger self, what advice would you give?
What’s something on your reverse bucket list (something you’ve done but never want to do again)?
Precious People Questions
If you had 20 minutes to call someone right now, who would you call? What would you like to talk about?
What’s a favorite story about a grandparent or other adult you looked up to?
Which teacher made the biggest impact on you? It could be a positive or a negative impact?
Who makes you laugh the hardest?
Who is the best gift giver you know?
Deep Discussion Questions
What’s a difficult decision you made this year? What was the outcome, and what would you do differently, if given the chance?
How do you define success?
What’s one achievable goal you have for the next season? How could loved ones encourage you and keep you accountable?
How do you want to be remembered, and what legacy do you want to leave?
What’s your reason for being?
The stories and lessons shared at your holiday table are part of your family’s legacy, and they can also open the door to important conversations about estate planning. Intentional dialogue about how you want to care for loved ones and leave peace of mind behind is one of the most meaningful ways to honor that legacy.
