7 Conversation Starter Games for Any Holiday Gathering (One is FREE!)
Fun conversation starter questions and games for anyone and everyone!

Get intentional, be authentic, and sprinkle some holiday cheer into your gatherings with our top picks for conversation starter questions & games. Perfect for everyone, whether you want to cozy up your love life or get teens chatting over cocoa by the fire.
Here are the 7 best conversation starter questions and games for anyone and everyone:
- Best Overall – TableTopics Tabletop Cubes
- Best for Holiday Travel – TableTopics to GO Travel
- Best Intimate – The Adventure Challenge Connection Cards
- Best for Groups of Friends – We’re Not Really Strangers Friendship Edition
- Best for Couples – Love Lingual
- Best for Deep Conversation – The Hygge Game
- BONUS: Best Free Game – “Would You Rather”
1. Table Topics has questions to start a conversation with literally anyone and everyone.
Best overall
These award-winning conversation starter games come in topics for all types of groups, including family gatherings, teens, grandparents & grandkids, and more!
Each game can even double as decor since they come in a sleek, clear cube, making you want to leave it out to play every day! 🤩
2. TableTopics even makes conversation starter questions that are perfect for your holiday traveling.
Best for holiday travel.
TableTopics to GO Travel – as low as $14 (reg. $20)
- Or shop individual travel packs for just $9 each.
You can even spark more meaningful conversations while traveling for the holidays! Whether you’re heading out on a long drive to visit family or cozying up for a quiet night at your holiday rental, these packs are the perfect travel companions to tuck in your suitcase.
Hip Tip: Speaking of Airbnb, here are ways you can score a cheap Airbnb rental!
3. The Adventure Challenge connection cards are great for spicing up any relationship.
Best intimate.
The Adventure Challenge Connection Cards – $14.99
Or get the In Bed Connection Cards for even less on Amazon.
These sleek, pocket-sized cards make the perfect stocking stuffer or holiday date-night idea! ✨ Whether you’re cozied up by the fire, wrapping gifts together, or traveling to see family, these conversation cards will spark small talk that makes a BIG difference in your relationship. ❤️
The creators spent years researching the most engaging conversations couples have, and each pack includes 50 unique questions and prompts to help you connect, laugh, and fall even more in love this season. Take them anywhere, from festive getaways to quiet nights in, and watch your bond grow with every card. 🎄
4. Love Lingual is best for couples, no matter how long you’ve been together.
Best for couples.
Love Lingual – $26.95
We heard that no matter how long you’ve been with your spouse or partner, this game couldn’t be more perfect for you and your favorite person! The Love Lingual conversation starter questions are thoughtfully curated with 5 different categories to ensure every topic of life is covered: Family, Intimacy, Couple, Individual, and Past and Future!
It’s never too late to get to know your partner better, and these questions are fun and powerful for rediscovering each other. It’s even likely to help you and your partner set goals and make future plans you may not have had before.
5. We’re Not Really Strangers makes the perfect game to get to know your friends better.
Best for groups of friends.
Having your besties over for a holiday get-together or festive game night? 🎁 Grab this game packed with 150 questions and wildcards to spark laughter, deep chats, and new memories this season! Each card is thoughtfully crafted across three levels: perspective, connection, and reflection, making it the perfect way to unwind with cocoa in hand and twinkle lights glowing. ✨
Designed for up to 6 players, this pack is guaranteed to bring everyone closer and add a little extra magic to your holiday gatherings. 🎄❤️
6. Create deep and meaningful conversations with a small, intimate holiday group with The Hygge Game.
Best for deep conversation.
The Hygge Game – $19.99
The Hygge Game is designed to create the ultimate warm and joyful atmosphere, encouraging friends and family to share stories, reflect on life’s big and small moments, and connect in a meaningful way. With over 300 thought-provoking questions, this game sparks laughter, heartfelt conversations, and lasting memories, perfect for a cozy night in, a festive dinner, or a small holiday party. ❄️☕️

7. BONUS: “Would You Rather?” is a game you can play without the need to buy anything at all.
Best free game.
Shop Would You Rather printables on Etsy if you need some inspiration!
The best part about “Would You Rather?” is that anyone can play, and it won’t cost you a thing since you come up with the questions yourself! 🎄 This simple conversation game is perfect for cozy holiday gatherings, long car rides to visit family, or snowy nights by the fire. Just think of two festive (or funny) scenarios and ask everyone which one they’d rather do!
For example: “Would you rather get stuck untangling Christmas lights or wrap presents for everyone in your neighborhood?” ✨
Kids especially love this game! It sparks their imagination and gets everyone laughing. The sillier the questions, the better! Need some inspiration? Head to ConversationStarterWorld.com for hundreds of creative ideas to keep the fun going all season long. 🎅🏼

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