Thanksgiving is one of our favorite times of year: the change of seasons, quality time with family and (let's not forget) pumpkin-spice ev-er-y-thing.

But for many, the holidays also bring the stress of confronting (or not confronting) family and friends who have differing values or beliefs — a conflict that’s particularly strong in today’s polarized political climate. While it can be difficult, this time can also be an opportunity. To reconnect and rediscover what makes us similar. To deepen relationships and spark new connections. To plug into our powers of empathy and understanding. A meaningful conversation can be the most powerful tool we have for bringing people together. Sometimes, all that is missing is the right questions.

With a multi-generational table, it can be hard to know what conversation-starters will draw out fun stories from a quiet uncle or keep a younger cousin engaged. Here are a few tips and questions we gathered to make your meal more memorable this November.

Atmosphere for a great conversation

Setting the atmosphere:

Keep it casual. Just because you are being intentional about asking questions doesn't mean this needs to feel like an interview. Keep things loose — ask follow-up questions, be interested, and be open!

Listen. A good conversation requires the people who are not talking to actively listen. Try and understand what someone is saying, without interrupting, talking over them or immediately rushing in with advice or a counter-story.

Be patient. Give time and space to the old, young, and shy to speak their mind. Everyone should get an equal chance to express themselves.

Make it fun! Sometimes asking a deep question can feel intense or awkward in a casual setting. This is where a game can help. Our deck of conversation cards takes the awkwardness away — you can always “blame the card” for asking the tough question :-).

A few easy questions to start the conversation:

Icebreakers are the appetizers of good conversation, giving us a taste of what's to come and leaving us hungry for more. Here are a few easy icebreaker questions to whet the table’s appetite:

  • What does a “perfect” day look like for you?
  • What is one dish your parents or grandparents made that you wish you could?
  • Describe a time you thought your parents were 100% wrong but eventually learned they were kind of right.
  • What is the kindest thing a stranger has ever done for you?
  • Has anything ever happened to you that you could not, and cannot, explain?
  • What are you grateful for? (a Thanksgiving classic)

Deeper questions for a more meaningful dialogue:

Now that everyone is warmed up, take things to the next level. These questions should help people dig deeper, open up, and share more meaningful thoughts, feelings and stories:

  • If you had two minutes to talk to yourself from 10 years ago, what would you say?
  • What message would you put on a billboard that thousands of people would see every day?
  • How did you or will you know you are in love?
  • Who in your life are you most grateful for?
  • When in your life have you felt like you could never fully repay someone?
  • If you could gift all humans one thing, what would it be?

We hope that these tips and sampling of questions from our Reflection Cards will help you host a warm and welcoming dinner.

Wishing you a wonderful Thanksgiving!


Holstee Reflection Cards

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This article is part of our series on the theme of Gratitude.

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Distilled from our Manifesto, positive psychology, the science of mindfulness, and ancient philosophic studies we have identified twelve themes core to living both fully and mindfully. We mapped these twelve themes to each of the twelve months in a year. Together with our community we explore one each month.