50 Conversation Starters to Spark Connection (and Keep Things Fun)

If there’s one thing you can count on with my family, we bring the fun. No matter the time of year—whether it’s the holidays or we’re just getting together—we’re an easygoing bunch. We’re easily entertained and don’t take ourselves too seriously. But we also know we’re not the norm, and not all family tables or gatherings are created equally. Sometimes, family dynamics can be difficult to navigate for any number of reasons. Because of that, Thanksgiving can be tough for some to get excited about. Thankfully, conversation starters exist to keep the focus on fun and cultivating meaningful conversations.

With the holidays right around the corner, we decided to lean into the spirit of what they’re really about: building connections and showing up with presence and curiosity. The good news is that these Thanksgiving conversation starters work for all gatherings, any time of the year. We hope these spark ideas for infusing levity and intention with your family or friends during this special, sacred season.

How to Spark Meaningful Connection This Holiday Season

The beauty of a good conversation starter is that it can shift the energy of a room instantly. Whether you’re sitting down with close family, reconnecting with friends, or meeting new faces for the first time, thoughtful questions can create space for everyone to feel seen and heard. And it’s not about asking anything groundbreaking—sometimes the simplest questions lead to the most meaningful exchanges. A lighthearted “What’s the best meal you’ve had this year?” can spark a conversation that lingers long after the plates are cleared.

Sometimes the simplest questions lead to the most meaningful exchanges.

But conversation starters are just one piece of the puzzle when it comes to hosting a seamless Thanksgiving gathering. Creating a warm, welcoming environment goes beyond what’s said at the table—it’s about thoughtful touches that make everyone feel comfortable and cared for. With a little planning, you can cultivate an atmosphere that feels as joyful and meaningful as the conversations shared. Consider exploring one or more of the ideas below.

Support Your Host or Ask for Support

One of the best gifts you can take off your host’s plate is logistics. Save the day and ask to “project manage” the holiday gathering. Want to make it even more fun? Pick a co-host. You’re helping with everything from coordinating:

Which guests bring what (drinks, appetizers, sides, desserts, etc.)
Table decor or utensils if needed
Who curates the playlist
Who helps with invites, name placements, etc.

It’s such a huge help when you can count on 1-2 people to pitch in and is a surefire way to build a beautiful and memorable experience together.

Bring Games

This is a fun time to get creative. There’s no shortage of card decks to generate fun and light conversations at the table, board games to appeal to all age groups, or good old-fashioned yard games set up in the backyard. I’m from the Midwest, so it’s not uncommon to see family playing cornhole before or after our holiday meal. And if your family is football-loving, you could spark a friendly betting pool on which team will win, who will sing the national anthem, or how many celebrities you can spot in the stands.

Pick a Family to Support Over the Holidays

Our family used to pick names for our Secret Santa every Thanksgiving, but as we’ve gotten older, we’ve become a family that chooses experiences and trips over gifts. That said, we love giving back, and in the spirit of making other’s holidays great, too, why not choose a family to support over the holidays? Everyone can pitch in a desired amount, and thanks to the help of organizations like the Salvation Army, they make it easy to find a family or kids to give back to during the holidays.

Create a New Tradition

Over the years, I’ve been inspired by families starting new traditions. A few ideas to consider as a group:

Run/walk your local Turkey Trot
Pick up trash around your morning lake walk
Volunteer at a shelter
Deliver blankets to shelters
Go to a performance, like the Nutcracker
Host a baking or cooking contest (the more pies, the merrier)
Take a family photo
Bake cookies and deliver to a hospital
Make a group video where everyone tosses out one goal they have for the year ahead and watch the video the next year during the holidays

There are endless possibilities for creating new traditions or connecting with family and friends in ways you haven’t before.

50 Thanksgiving Conversation Starters to Spark Meaningful Connection

We don’t think this is a novel or groundbreaking idea, but the sheer intention behind asking great questions goes so far. If you’re not into a card deck that prompts questions, you could either make your own, ask everyone to contribute and pull out of a hat, or simply come prepared with a few of your own. This is especially great if you’re attending a holiday as a new partner, a guest, or want to get to know your own family or friends more intimately.

It’s helpful to have a few topics in your back pocket for those moments when conversation stalls or takes an unexpected turn. From gratitude-focused questions to ones that tap into childhood memories or future dreams, these Thanksgiving conversation starters are designed to foster connection without feeling forced. After all, a great holiday isn’t about the perfect meal or flawless decor. It’s about being fully present and making memories with the people gathered around the table.

Thoughtful Conversation Starters

What are you most thankful for this year?
What’s one thing you want to accomplish before the year ends?
What’s your best takeaway or learning from this year?
If you had five minutes to call someone right now, who would it be?
Where is one place you’ve visited that surprised you?
What do you hope your legacy in life is?
What’s one thing you’ve done this year that made you proud?
Who has impacted your life the most this year?
What’s a new habit or routine you’ve adopted recently?
What’s one lesson you wish you’d learned sooner in life?

Light-Hearted Conversation Starters

What would your Real Housewives tagline be?
What’s the best purchase you made this year?
What’s something you can’t stop talking about?
If I gave you $100 right now, what would you do with it?
How often do you use Amazon/Instacart/Uber Eats?
What’s the funniest thing that happened to you recently?
What’s one food you refuse to eat—even on Thanksgiving?
If you could swap lives with a celebrity for a day, who would it be?
What song is currently stuck in your head?
If your life were a movie, what genre would it be?

Conversation Starters for Close Friends and Family

What do you think people would say your best quality is?
What’s one thing on your to-do list that you keep putting off?
What family tradition means the most to you?
If we could plan a group vacation anywhere in the world, where would we go?
What’s one thing we should do together more often?
What’s a hidden talent you’ve never shared?
If you could relive any moment we’ve had together, which one would it be?
What’s the best piece of advice a family member has given you?
Who makes you laugh the hardest at the dinner table?
How do you prefer to spend quality time with people you love?

Introspective Conversation Starters

What do you wish more people understood about you?
What’s the hardest decision you’ve made this year?
How do you handle stressful situations during the holidays?
What’s a personal value you hold close to your heart?
If you could change one habit, what would it be?
What motivates you to keep going when things get tough?
How do you recharge when you’re feeling overwhelmed?
What’s something you’ve learned about yourself this year?
If you could sum up this year in one word, what would it be?
How do you define success for yourself?

Playful Conversation Starters

If you could invent a holiday, what would it celebrate?
What’s your go-to karaoke song?
If you had to eat one meal for the rest of your life, what would it be?
What superpower do you wish you had?
If you could teleport anywhere right now, where would you go?
Which fictional character do you relate to the most?
What would you do first if you won the lottery tomorrow?
If you could only wear one outfit forever, what would it be?
Which animal best represents your personality?
What’s the weirdest dream you’ve ever had?

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50 Conversation Starters to Spark Connection (and Keep Things Fun)