Connecting Across Generations: Holiday Questions That Go Beyond Small Talk

Dec 7

The holidays can be a time for slowing down, bringing people together, and reconnecting over our favourite traditions but let’s be real: they can also feel hectic, rushed, and lacking on the deeper type of connection that so many of us crave. Many older adults tell me that what they want most isn’t a fancy gift or a perfect dinner. What they want is connection. Someone taking a genuine interest in their stories, their history, and the wisdom they’ve gathered along the way.

If you’re hoping to deepen your conversations with an older adult in your life this year, whether that be a parent, grandparent, neighbour, mentor, or family friend, here are 15 meaningful conversation prompts that can spark warm memories and deepen understanding.

Use these around the table, in the car, during a walk, or while sharing a cup of tea. They can help open the door to storytelling in a safe, comfortable way.

· What’s one holiday memory that always makes you smile?

· Who was the person in your life who made the holidays feel special when you were growing up?

· Is there a tradition from your childhood that you wish people still did today?

· What’s one piece of wisdom you’d pass along to the younger generation in our family?

· What’s something you’re proud of from this past year?

· Who were the people who shaped you the most when you were younger?

· What’s a story from your early adulthood that not many people know?

· What music, movies, or books always remind you of this time of year?

· What’s the best gift you ever gave someone? What made it meaningful?

· Is there a life lesson you learned the “hard way” that you now appreciate?

· What changes in the world have surprised you the most in your lifetime?

· What’s something you’re looking forward to in the coming year?

· If you could relive one holiday from your past, which one would it be and why?

· What food, scent, or small ritual instantly brings back memories for you?

· What’s something you want our family to remember or carry forward in the future?

Connection is a powerful antidote to stress, loneliness, and the emotional complexity that the holidays can bring, especially for older adults. These prompts offer a gentle way to move beyond small talk and toward the types of conversations that create meaning, belonging, and emotional closeness. Consider this an invitation to slow down, get curious, and allow stories to bring your family a little closer this season.

This post is for informational purposes only and should not be considered therapeutic advice or a replacement for individual therapy. For more information on locating a psychologist near you, please contact your family doctor, the Ontario Psychological Association, the Canadian Association for Cognitive Behavioural Therapy, or Psychology Today