61: Start Better Conversations This Thanksgiving

In this special holiday episode, Keith and Doug share over 20 meaningful Thanksgiving conversation starters designed to help your family connect on a deeper level. Whether your gatherings lean peaceful, chaotic, sentimental, or hilarious, this episode gives you tools to do something different and bring more harmony, curiosity, and gratitude to the table.

Drawing from stories that range from childhood traditions to New York City parades to unexpected life lessons, Keith and Doug unpack how simple, intentional questions can shift the tone of your entire holiday. Instead of drifting into politics or tension, you’ll learn how to redirect conversations with kindness, spark meaningful dialogue, and create shared memories that actually last.

For example, here are some questions you can ask:

• Tell me about the Thanksgiving table when you were 12 and last year.
• How far back would the oldest person at the table have known someone?
• What are 2 holiday traditions you enjoyed then and now?
• When should Christmas decorating begin?
• Turkey or ham for Thanksgiving? Why?
• What is one thing your mom taught you? Your dad?
• Have you ever worked 60 hours in a week? Why?
• What’s your hardest job ever?
• What’s the weirdest job a relative has ever done?
• Have you ever eaten at a nice restaurant alone?
• What’s your oldest family tradition?
• What’s a place tied to your childhood that no longer exists?
• What’s a moment from your past that most wouldn’t know?
• Has your family kept a secret/mystery alive?
• If your life was a chapter in a history book, what would you title it?
• Name a forgotten childhood trend you were involved in?
• What’s an outdated rule your parents insisted on?
• Who in the past do you wish you had asked more questions?
• When did you feel you first became ‘you’?
• What story explains more about you than people realize?
• What’s a smell or sound that instantly takes you somewhere else?
• What object from your past will you keep?

This episode is perfect for families looking to cultivate connection—especially those balancing busy lives, financial responsibilities, and multigenerational dynamics. If you want your Thanksgiving to feel more grateful, more human, and more enjoyable, you’re in the right place.

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