90+ Fun Holiday Icebreaker Questions | Funny | Work 2024

As the holidays approach, you may find yourself hosting a holiday party or attending one.

I’ll give you some straightforward advice if you have to attend one of these events despite not being a party animal: just be ready.

Let the host introduce you to people, and then use these fun Holiday icebreaker questions to make a fun impression.

After all, these parties are supposed to be interesting and entertaining. 

I’ve therefore created a list of funny icebreaker Questions to play part games that are appropriate for the holidays.

Funny Ice Breaker Questions That Will Have You In Stitches

Funny Ice Breaker Questions
  1. What’s the worst thing you ever did as a kid — and got away with?
  2. What’s the craziest fashion trend you ever rocked?
  3. What are your favorite songs from your teenage years that you still rock out to when nobody else is listening?
  4. Who was your childhood actor/actress crush?
  5. What’s the most embarrassing moment from your teen years?
  6. What’s the craziest dare you ever took?
  7. What did you get into the most trouble for with your parents as a kid?
  8. What’s your silliest memory with your best friend?
  9. What part of elementary school do you wish you could incorporate into your adult life? (i.e. naptime)
  10. What was the first concert you ever went to?
  11. Do you have any crazy roommate stories?
  12. What’s the grossest food you ever had to eat to be polite?
  13. What’s the strangest family tradition in your family?
  14. What was your favorite item of clothing as a kid?
  15. What did you name your first car?
  16. What Disney/cartoon character were you inexplicably afraid of as a kid?
  17. What was the first record, tape or CD that you ever owned?
  18. What’s the story of your first crush?
  19. What was your first job? What did you like/dislike about it?
  20. Who was the worst grade-school teacher you ever had?
  21. What afterschool activity did you quit as a kid, and why?

Fun Holiday Icebreaker Questions At Work

Fun Icebreaker Questions At Work
  1. Have you ever regifted a present?
  2. Have you ever returned a present you did not like for store credit?
  3. What would your elf name be?
  4. Which of your coworkers is most likely to be an elf in disguise?
  5. Which of your coworkers is likeliest to wait until the last minute to finish Christmas shopping?
  6. Which of your coworkers would be the best department store Santa?
  7. Would you rather be reincarnated as a cat or a dog?
  8. Pull out your phone; what is your most used emoji?
  9. Who was your childhood famous crush?
  10. Imagine you are a professional baseball player. What is your introduction song?
  11. Pick your favorite decade. Tell us why.
  12. You are stranded on a remote desert island. Are you alone or with your worst enemy?
  13. What is the best thing you have bought so far this year?
  14. Who is the most interesting Disney character?
  15. What Christmas carol gets stuck in your head the most?
  16. What Christmas-themed food do you think is the grossest?
  17. Describe what your ghosts of Christmas past, present, and future would look like.
  18. What song would you kill during Christmas karaoke?
  19. What is the best super power?
  20. Share one holiday “scrooge” moment you had.
  21. What is your “never again” holiday story?
  22. What is the strangest thing you have ever used/seen used for wrapping paper?
  23. What would you be most offended to receive as a Christmas gift?
  24. Be honest: is it really the thought that counts?
  25. What is the most controversial Christmas opinion you have?
  26. What celebrity do most people say you look like?
  27. If you could try any food, what would it be?
  28. What dog breed would you be?
  29. Have you ever met your idol?
  30. What bucket list item do you most want to check off in the next six months?
  31. Imagine you can instantly learn any language. Which would you choose?
  32. Do you prefer big dogs or small dogs?
  33. Show us your most-used emoji.

Ice Breaker Questions About Holidays

Ice Breaker Questions About Holidays
  1. Which Winter holidays do you celebrate?
  2. What’s the best gift you’ve ever received over the holidays?
  3. What’s one gift you’re secretly hoping to receive this year?
  4. What’s your favorite outdoor winter activity?
  5. What was the best snow day of your childhood that you can remember?
  6. What’s your craziest NYE story?
  7. What’s your favorite indoor activity for when it’s too cold outside in Winter?
  8. What’s the worst holiday gift you’ve ever received?
  9. What’s the worst holiday gift you’ve ever given to somebody else?
  10. What’s your most embarrassing reaction to receiving a gift?
  11. What’s that one gift you really wanted when you were younger that you never got?
  12. Have you ever had a dreidel made out of clay?
  13. What are your favorite foods that you only eat during Hanukkah?
  14. How do you feel about Adam Sandler’s Hanukkah Song?
  15. Do you like snow?
  16. Do you celebrate Christmas? If so, do you enjoy Christmas?
  17. Did you believe in Santa Claus as a child? Until what age?
  18. Can you name all of Santa’s reindeer?
  19. If you were one of Santa’s reindeer, which would you be and why?
  20. Christmas trees…. do you go with real or fake? Debate why!

Fun Questions For An Icebreaker

Fun Questions For An Icebreaker
  1. White Christmas tree lights or multi-colored lights?
  2. Twinkling lights or static lights?
  3. Have you ever roasted chestnuts on an open fire?
  4. Are you an expert gift wrapper? Wrapping paper or gift bags?
  5. Have you ever decked the halls with boughs of holly?
  6. How early do you put up your Christmas tree, lights, and holiday decorations?
  7. Are icicle lights hanging from the roof… beautiful or tacky?
  8. Which celebrity would you want to meet under the mistletoe?
  9. When do you start listening to Christmas music? Or do you never listen to it?
  10. What’s your favorite Christmas song? Favorite Winter/holiday song in general?
  11. What’s one holiday song you just can not stand?
  12. Which character in Rudolph the Red Nosed Reindeer do you most relate with?
  13. If you were an elf, what would be your name? What toy would you make?
  14. If you were Santa Claus, would you give coal to the bad kids, or give them something else?
  15. What’s your favorite thing to do on Christmas Eve?
  16. Candy canes… meh or heck yea?

Share these Holiday icebreaker Questions with your friends as well, and let them make a fun impression.

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