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Thanksgiving week is upon us, ushering in several weeks of seasonal festivities, gatherings, and vibrant (or awkward) time with loved ones. Conversation in these settings can be natural and filled with joy, or uncomfortable and deeply dreaded. If you find yourself struggling to make conversation at your next Thanksgiving or Christmas get-together, this list is for you!

I’ve compiled 28 lighthearted questions that will get you reflecting about some best and worst holiday moments. And if you’re more of the solitary type, these are fun to answer on your own! I know I sure had fun pondering my own answers.

1. The Thanksgiving meal would not be complete without _____________.

2. Have you experienced a Thanksgiving meal disaster?

3. What is the strangest thing (object, circumstance, person, etc.) you are thankful for?

4. If asked to send a letter of gratitude to a historical figure, who would you choose and why?

5. If you were given the opportunity to design a float for the Macy’s Parade (or for the Rose Parade), what would it look like?

6. What is the most meaningful Christmas gift you have given and/or received?

7. What is your most vivid (positive or negative) holiday memory?

8. What decorative holiday item do you get most excited about pulling out each year?

9. If you were an elf, what would your name be and whose shelf would you like to visit?

10. What holiday tradition is overrated?

11. What is a holiday tradition you would like to add this season?

12. Describe your ideal Christmas morning.

13. What is the worst (or best) Christmas movie and/or song?

14. When is it okay to begin listening to Christmas music?

15. What classic Christmas movie would you happily step into?

16. What are you least looking forward to this Christmas season?

17. Describe the coolest Advent calendar you’ve ever seen.

18. If you could choose gifts to receive on the Twelve Days of Christmas, what would they be? (Remember that the item count accumulates with each day, with previous gifts repeating!)

19. If you had to choose one holiday song (or album) to be on repeat from now until Christmas day, what would it be?

20. Describe an ideal Christmas party (decor, guest list, setting, menu, attire, entertainment, etc.).

21. Would you rather experience a white Christmas at a mountain resort, or a tropical Christmas on the beach?

22. What is the best/worst pumpkin-flavored item you have ever tasted?

23. What popular seasonal flavor or treat needs to be permanently retired?

24. If money and circumstances were not a concern, what Christmas gift would you love to give?

25. Santa is asking for help naming the next generation of his eight reindeer. What should he name them?

26. What is the best/worst New Year’s Resolution you’ve ever made?

27. What resolution do your loved ones wish you would make for the coming year?

28. Make your best prediction (personal, cultural, global, etc.) for 2024.

I wish you some very happy and insightful conversations in the coming weeks. Feel free to share your best responses!

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