48 festive questions to ask at all of your holiday gatherings

Relationships

Oct 20

Written By Calm Editorial Team

Clinically reviewed by Dr. Chris Mosunic, PhD, RD, MBA

Stressed about small talk or awkward pauses at a holiday party or dinner? These 48 holiday questions can spark connection and even laughter at all of your festive gatherings.

The holidays have a way of amplifying everything — joy, grief, nostalgia, and of course, a few awkward pauses. If you find yourself at a holiday table, sandwiched between a distant cousin and your mom’s friend from book club, you might be searching for something—anything—to say that isn’t a commentary on the weather. A few moments of silence are totally normal, and with any social gathering, conversation ebbs and flows. But if the event is dominated by too much ebb, a few holiday questions can come in handy.

Having a list of fun, lighthearted prompts ready can take the pressure off and keep conversations flowing, whether you’re at a family dinner, an office party, or a cozy gathering with friends. These questions are short, genuine ways to spark laughter, curiosity, and connection across any table.

Let’s dive into these festive icebreakers and conversation starters for every kind of holiday moment so you can focus less on what to say next and more on actually enjoying the holiday season.

48 questions to get conversation flowing during the holidays

No one loves an awkward pause, especially during a time of year that is meant to be merry and bright. So having a few holiday conversation starters in your pocket can give you the confidence to know that you can have interactions that are truly connective.

Here are 48 festive questions you can ask to help you find connection and fun in your conversations.

Holiday dinner table questions

Dinner tables can be both comforting and chaotic, depending on the gathering. So, here are some calming questions that can help spark warmth, nostalgia, and maybe even a little laughter.

What’s the one holiday dish you always make room for, even if you have to switch into more comfy pants to do it?
If our family (or friend group) celebrated the holidays in another country, where would you choose, and why?
What’s a holiday tradition that’s faded over time but you’d love to bring back?
What dish on the table will you always go for first? And maybe even secretly takes seconds of?
What’s one small holiday habit that makes you feel more grounded each year?
Who from history would you love to have at this table, and what would you ask them?
What holiday gift did you get as a child that you got the most excited for?
What’s one simple thing you’re grateful for right now? (It can be as small as the food on the table.)

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Holiday party icebreaker questions

Whether it’s an office mixer or a neighborhood get-together, holiday parties can offer a wide range of small talk. To help you navigate this, here are eight light questions that are connective but don’t require deep introspection.

What’s the most memorable holiday party you’ve ever attended? And why?
Would you rather wrap gifts for hours or untangle Christmas lights?
What’s your go-to holiday snack or drink?
If this party had a soundtrack, which song would be playing right now?
Which holiday movie would you most want to live inside for a day?
What’s one tradition you love every year?
What’s the oddest or funniest gift exchange story you’ve witnessed?
If you could give everyone here one small gift, what would it be?

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Holiday-themed small talk questions

During the holidays, conversation tends to happen in motion, like when someone’s grabbing a dessert or waiting for a drink. To make the most of these interactions, here are some questions that can turn these fleeting moments into genuine connection.

If you celebrate Christmas, do you go for a real tree or an artificial one? And would you ever switch it up?
What’s your stance on matching holiday pajamas: charming or never in a million years?
Which holiday scent instantly feels like home to you?
When is it okay to officially start decorating for the holidays? And when do you call it quits?
What’s your favorite holiday movie that you must watch every season?
Is snow major for you, or is it just majorly inconvenient?
What’s one holiday song you never get tired of? And one you never want to hear again?
What’s your favorite low-effort holiday ritual?

Fun kid-friendly holiday questions

Kids are the unofficial mood boosters of any holiday gathering. They bring imagination, honesty, and the occasional sugar-infused chaos. These questions help keep them engaged and can be pulled out at any dinner table.

If you could help Santa for one night, what job would you want?
What would your reindeer name be? And what would your elf name be?
If you could make your own holiday, what would people celebrate? And what would they eat?
What’s your favorite holiday treat, besides candy?
What’s one gift from Santa that your pet would like?
Would you rather build a snowman or decorate cookies?
If you could make one toy come to life, which would it be?
What’s one nice thing you could do for someone this holiday season?

Deeper holiday conversation starters

Not every gathering needs to stay surface level. Sometimes, when the room softens and people start to relax, it feels right to go a little deeper. When this happens, here are eight thoughtful and connecting questions you can ask.

What part of the holidays feels most meaningful to you?
What’s something you’ve learned this past year that changed you for the better?
Which memory from past holidays do you think about the most?
What’s a tradition you’d love to start or stop? And why?
What’s one thing you’re grateful for this year that surprises you?
Who or what has made your year a little brighter?
What does “home” mean to you right now?
What’s one way you’d like to show more kindness, to others or to yourself, in the new year?

New Year’s Eve party questions

As the clock edges closer to midnight, many conversations drift toward the year ahead. To bridge this gap between celebration and reflection, here are some natural conversation starters you can bring up.

How would you sum up this year in one word?
What’s something small that made a big difference over the last 12 months?
If you could relive one day from this year, which would it be?
What’s one thing you’re proud of, even if no one else noticed?
What’s a habit or mindset you’re ready to leave behind?
What’s one thing you want to try next year?
If your year had a title, what would it be?
What message would you send to your future self, one year from now? And what’s one that you’d send to yourself one year ago?

Holiday questions FAQs

What are some fun holiday-themed questions for kids?

Children connect through play and creativity, so the best questions tend to be imaginative and open-ended. Try questions that invite storytelling, like, “If you could help Santa for a night, what job would you want?” or “What would your reindeer name be?”

Questions around animals, make-believe, and favorite treats are also good options that usually keep their attention.

What are meaningful holiday questions for family dinners?

Meaningful questions work best when they stay personal but are also not too probing. Memories, gratitude, and hopes for the year ahead are good areas to focus on as they allow people to share without feeling put on the spot.

Try something like, “What’s something you’ve learned this past year?” or “What’s a small moment that made you smile recently?”

Are there inclusive holiday icebreaker questions that aren’t Christmas-specific?

Absolutely. Food, travel, music, memories, and wintertime rituals are all topics you can focus on that won’t leave people feeling left out. Try neutral options like, “What’s your favorite seasonal dish?” and “What’s one cozy thing you look forward to this time of year?”

Also, as a rule of thumb, keep your language neutral and lean on words like “holiday” or “season” instead of “Christmas.” This helps set an inclusive tone for any group.

How do I keep holiday small talk from feeling forced?

Practice genuine curiosity when you ask questions. Also, instead of cycling through surface topics, listen for openings you can follow up on. If someone shares a story about a travel destination that you love, you might ask how they liked it, where they stayed, what the highlights were, instead of bouncing to the next topic.

Asking open-ended questions is another great way to connect. Avoid rushing to fill every silence. And when in doubt, ground the conversation in shared experiences like food, décor, travel, or local traditions. This can keep things comfortable and organic.

What sort of icebreaker questions would be suitable for a work Christmas party?

Work holiday gatherings are their own delicate ecosystem. You want to keep things fun and festive, but still professional. So in this situation, the best type of questions are light and inclusive. Plus, they focus on shared experiences like holiday movies, travel dreams, or favorite office traditions.

Try nonpersonal questions like, “What’s your favorite holiday snack you can not get enough of?” or “What song would you add to the office party playlist?”

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Calm Editorial Team