Holiday Icebreaker Questions for Virtual Holiday Parties, Hybrid Teams and Work Events
Originally published December 2021 by Brian Donahue • Updated May 2026 by HOST Events
Icebreakers?
We’ve all been there. The get-together with coworkers, friends, or extended family where the conversation doesn’t exactly… well, let’s just say it doesn’t get off to a strong start.
Did we talk about the weather? Check.
Did we ask each other what we did last weekend? Yup.
Already talked about the big game or trending TV show earlier in the week? Best not to circle back.
Now what do we talk about?
Whether your team is remote, hybrid, traveling, or gathering together in person for the holidays, meaningful conversation and shared laughter help create stronger connections. One of the easiest ways to get people talking is with a great icebreaker question.
Icebreakers are prompts designed to move conversations beyond everyday small talk and encourage more engaging, memorable interactions. They can help teams relax, spark laughter, uncover shared interests, and make group settings feel more welcoming and interactive — especially during holiday gatherings and end-of-year celebrations.
At HOST Events, we’ve seen firsthand how the right opening question can completely shift the energy of a virtual holiday party, company celebration, or team building event. To help get the conversation flowing this holiday season, we’ve put together this list of festive holiday icebreaker questions. Enjoy!
Holiday & Winter Icebreaker Questions
Holiday celebrations are a popular time for companies to bring teams together, reflect on the year, and celebrate shared successes. Whether your coworkers are remote, hybrid, traveling, or spread across multiple offices, holiday icebreaker questions can help spark conversation and make seasonal gatherings feel more connected, engaging, and fun.
To help get the conversation flowing, try kicking off your next virtual holiday party, team celebration, or end-of-year event with a few of these festive icebreaker questions.
Which winter holidays do you celebrate?
What’s the best gift you’ve ever received during the holidays?
What’s the worst holiday gift you’ve ever received?
What’s a holiday tradition you look forward to every year?
What’s that one gift you really wanted as a kid but never got?
What’s one gift you’re secretly hoping to receive this year?
What’s your favorite outdoor winter activity?
What’s your favorite indoor activity when it’s too cold to go outside?
What’s your favorite holiday movie or guilty pleasure watch?
Ugly sweaters — are you in or out?
What seasonal food or dessert do you look forward to every year?
What song instantly puts you in a holiday mood?
Do you prefer snow days or cozy rainy days?
What was the best snow day from your childhood?
What’s your ideal way to spend a holiday weekend?
Hot chocolate or apple cider?
What’s your favorite holiday decoration?
If you could celebrate the holidays anywhere in the world, where would it be?
What’s the earliest holiday decorations should go up each year?
What’s one holiday tradition you would gladly skip forever?
Where is your favorite place to spend the holidays?
What’s your favorite holiday scent — cookies, pine, fireplace, peppermint, something else?
What’s your go-to holiday snack while watching movies?
What’s your favorite thing about winter?
What’s your most memorable New Year’s Eve?
What holiday food deserves more hype?
What’s your favorite childhood holiday memory?
What’s one thing that instantly makes the holidays feel nostalgic for you?
Christmas Icebreaker Questions
Christmas celebrations often bring out strong opinions, nostalgic memories, family traditions, and plenty of holiday debate. From Christmas music and twinkling lights to gift wrapping skills and candy cane loyalty, these Christmas icebreaker questions are designed to spark conversation, laughter, and a little festive chaos during your next holiday gathering.
Do you celebrate Christmas? If so, what’s your favorite part of the season?
Did you believe in Santa Claus as a child? Until what age?
Can you name all of Santa’s reindeer?
If you were one of Santa’s reindeer, which would you be and why?
Real Christmas trees or artificial trees? Defend your choice.
White lights or multicolored lights?
Twinkling lights or static lights?
How early do you put up holiday decorations?
Icicle lights — festive or tacky?
When do you officially start listening to Christmas music?
What’s your favorite Christmas song or holiday song in general?
What’s one holiday song you absolutely cannot stand?
If there was only one thing underneath the tree for you this year, what would you hope it would be?
Eggnog — delicious or absolutely not?
Have you ever made mulled wine or hot cider at home?
Do you think your team could successfully name all 12 Days of Christmas together?
Have you ever roasted chestnuts on an open fire?
Are you great at wrapping gifts or do you rely on gift bags?
Mistletoe — festive tradition or awkward tradition?
Who do you typically celebrate Christmas with?
What’s your family’s go-to Christmas Day activity?
If Santa didn’t have a sleigh, what would he drive instead?
Which character from Rudolph the Red-Nosed Reindeer do you relate to the most?
If you were one of Santa’s elves, what toy would you make?
If you were Santa Claus, would you give coal to the naughty list or something more creative?
What’s your favorite thing to do on Christmas Eve?
Candy canes — overrated or iconic?
Did you leave snacks out for Santa as a kid? What did you leave?
What’s your favorite Christmas cookie?
What toy or gadget completely dominated your childhood holiday wish list?
What’s your favorite Christmas movie quote?
What’s the most chaotic thing that has ever happened during one of your holiday celebrations?
More Icebreaker Questions, Team Building Ideas & Holiday Event Inspiration
Looking for even more ways to spark conversation and boost engagement during meetings, holiday parties, and company events? Explore our full list of fun icebreaker questions for virtual meetings, hybrid teams, onboarding sessions, and team building activities.
Planning a holiday celebration for your team? HOST Events offers professionally hosted virtual events, in-person experiences, holiday games, tastings, wellness sessions, chef-led experiences, and interactive team building activities designed to foster connection and ignite engagement during the busiest season of the year.
Need help planning your next holiday event? Explore HOST’s seasonal experiences or schedule a planning chat with our team today.
🎄 Planning a holiday event for your team?
HOST Events offers professionally hosted virtual events, holiday games, chef-led experiences, tastings, wellness sessions, and interactive team building activities designed to foster connection and ignite engagement during the busiest season of the year.
Explore Seasonal ExperiencesSchedule a Planning Chat
Continue Exploring HOST Ideas
Looking for more ways to strengthen workplace culture, boost engagement, and create memorable company celebrations? Explore more seasonal inspiration and team building ideas from the HOST Blog.
