50+ Holiday Icebreaker Questions for Work

The holiday season is a perfect time to connect with your team, learn about different traditions, and celebrate what makes each person’s holiday experience unique. Whether you're hosting a virtual holiday party or an in-person gathering, these questions can help spark engaging conversations and create an inclusive environment that spreads the holiday spirit. 

Here are holiday-themed icebreaker questions that can work for any team:

Lighthearted & playful holiday icebreakers 😆

1. If you had to eat one holiday treat for the rest of the season, what would it be?
2. What’s the most unusual holiday/Christmas gift you’ve ever received during the holidays?
3. Imagine you’re in charge of planning the office holiday party. What’s the theme, and what activities are included?
4. If you could have any famous holiday figure (Santa Claus, Frosty, etc.) as a co-worker for a day, who would it be and why?
5. If you had to choose a holiday to celebrate every single month, which one would it be and why?

Icebreakers for gratitude, reflection, & fun 🥳

6. What’s one thing you’re especially grateful for this holiday season?
7. Do you have a favorite memory from past holidays, whether personal or work-related?
8. If you could invite any three people (living or historical) to a holiday party, who would they be and why?
9. What's one way you’ve spread holiday cheer to others this year?
10. What’s a funny or embarrassing holiday mishap you’ve experienced?
11. Do you participate in any volunteer work or charitable activities during the holiday season?
12. What’s a New Year’s resolution or goal you’re setting for yourself in the coming year?

Icebreakers on traditions from around the world 🌎

13. Have you ever celebrated a holiday from a different culture? What was your experience like?
14. If your family or friends celebrate multiple holidays, how do you balance or blend the celebrations?
15. What’s one holiday tradition from your culture that you’d like others to learn about or try?
16. Have you ever attended or participated in a winter festival or event that’s unique to your area or culture?
17. For those who celebrate the Lunar New Year, do you have any specific traditions or favorite foods?
18. If you could start a new holiday tradition, what would it be?
19. Are there any regional holiday foods or desserts that your family makes every year?

General holiday icebreakers ❄️

20. What’s your favorite holiday tradition in the winter, and how did it start in your family?
21. What’s your go-to holiday movie or winter TV special?
22. Do you prefer a snowy winter wonderland or a warm holiday destination? Why?
23. What’s your favorite seasonal food or drink during the holidays?
24. What’s one unique holiday tradition you’ve experienced or heard about from another culture?
25. Is there a holiday song that you find yourself playing on repeat?
26. If you could spend the holidays anywhere in the world, where would it be and why?
27. Do you enjoy giving a holiday present or receiving them more? What’s the coolest gift you've ever given?
28. What’s one thing that always gets you in the holiday spirit?
29. Do you have any winter-related hobbies or activities you look forward to each year?
30. How do you typically ring in the New Year? Do you have any special traditions?
31. What's your family's funniest holiday story?

Christmas icebreaker questions 🎄

32. What’s your favorite Christmas tradition, and how did it start in your family?
33. Do you open Christmas presents on Christmas Eve or Christmas Day? Is there a reason behind it?
34. What’s the most memorable Christmas gift you’ve ever received?
35. Do you prefer a real or artificial Christmas tree? Are there any special ornaments you always use?
36. What’s your favorite Christmas movie or TV special, and why?
37. If you could invite any character from a Christmas movie to your holiday party, who would it be?
38. What’s your go-to Christmas party dish or dessert that you always make or enjoy?
39. What’s one thing that always gets you in the spirit to celebrate Christmas?
40. Do you have a favorite Christmas song or carol? Are you a fan of holiday music in general?
41. What’s one unique Christmas tradition from another culture that you find fascinating?
42. Do you have your own ugly Christmas sweater and if so, what's on it?
43. Do you prefer a white Christmas or a tropical one?

Hanukkah icebreakers 🕎

44. What’s your favorite part of the Hanukkah celebration?
45. Do you have a favorite way to prepare or eat latkes or sufganiyot (jelly donuts)?
46. How does your family or community celebrate the lighting of the menorah? Any special traditions?
47. What’s the best Hanukkah gift you’ve ever received or given?
48. How do you play dreidel, and what’s the best or funniest thing you’ve ever won with it?
49. Is there a specific night of Hanukkah that holds special significance for you? Why?
50. Do you have a favorite memory from a past Hanukkah celebration?
51. How do you explain the significance of Hanukkah to people who may not be familiar with it?
52. What’s one thing you wish more people knew or understood about Hanukkah traditions?

Kwanzaa icebreakers 🎁

53. How do you and your family or community celebrate Kwanzaa? Any specific rituals or practices?
54. Which of the seven principles (Nguzo Saba) of Kwanzaa resonates with you the most, and why?
55. What’s your favorite Kwanzaa dish or meal that you enjoy during the celebration?
56. How do you incorporate the Kwanzaa colors (black, red, and green) into your celebration?
57. What’s your favorite way to light the kinara, and do you have a special ceremony for it?
58. What’s a Kwanzaa tradition you’ve passed down or hope to pass down to others?
59. What’s a powerful Kwanzaa story or lesson that has stuck with you over the years?
60. How do you use Kwanzaa as a time for community building or connection with others?

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Break the ice with Confetti 🥳

No matter what holidays your team celebrates, the spirit of the season is about connection, reflection, and gratitude. By using these holiday icebreaker questions, you can create a festive and inclusive atmosphere that allows everyone to share their traditions and experiences. 

There’s more where those came from 👉 If you want to enjoy a guided round of festive icebreakers with your team, book a round of Holiday Water Cooler with Confetti! 

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