The holidays are just about here, and for many of us, that means time with family. Between the meals, games, and movie marathons, there’s something else worth making time for: conversation. Not just about who’s bringing dessert or what gifts are still on the list, but about the stories that make your family who they are.

I recently came across an old article by anthropologist Elizabeth Keating in The Atlantic. She talked about how often we forget to ask our relatives the deeper questions—the ones that reveal what life felt like when they were younger. But I wonder if part of what holds us back is simply not knowing where to begin.

So here’s a list of questions—some inspired by Keating’s work, others just for fun—to help spark meaningful, funny, and unforgettable conversations this holiday season.

Conversation Starters for Kids and Adults

  1. What did you see when you looked out your bedroom window as a kid?

  2. What was the best advice you ever got from a family member?

  3. What’s a tradition you loved as a kid that you wish would come back?

  4. What was your favorite toy or game when you were my age?

  5. Did you ever get in trouble at school? What happened?

Forward-Looking Questions

Here are a few fun, future-focused questions to get everyone thinking:

  1. If you could teach the next generation just one thing, what would it be?

  2. What’s something you hope our family will always do, even years from now?

  3. What’s a dream or goal you still want to accomplish?

  4. What’s something you’re excited about for the year ahead?

Whether you're gathered around the dinner table, curled up on the couch, or taking a quiet walk after a big meal, these questions can spark the kind of stories and moments that bring families closer, this season and beyond.