30 Icebreakers Guaranteed to Add Some Spice to Holiday Gatherings

With the holidays quickly approaching, many of us will be coming together for festive celebrations. Whether it’s a partner’s company party or dinner with your family, too many of these gatherings won’t include anything more than pleasantries. Or worse, they’ll devolve into dicey territory.

To help spark fun conversations, we’ve collected a wide selection of fun (and funny) prompts guaranteed to get people talking. Whether you use them all or just a few, they’re sure to elicit some laughs and maybe even bring folks closer together. That’s what the holiday season is about after all – coming together and making memories with your nearest and dearest.

P.S. You may want to record answers to these questions into a hardcover book of stories with Remento today.

30 Conversation Starters for Holiday Gatherings

1. What was the most memorable gift-opening moment from your childhood?
2. If you could permanently delete one holiday song from the world, what would it be?
3. What’s a favorite family holiday ornament and why is it special?
4. What holiday dessert best describes you and why?
5. What’s the worst holiday gift you’ve ever received?
6. Icicle lights hanging from the roof… beautiful or tacky?
7. If you could spend the holidays anywhere in the world, where would you go?
8. If you were one of Santa’s reindeer, which would you be and why?
9. How old were you when you stopped believing in Santa?
10. What is your go-to holiday karaoke song?
11. What’s one holiday tradition you could do without?
12. What was the best gift you ever gave?
13. What is your favorite holiday-themed cocktail or drink?
14. If you could have any holiday superpower, what would it be?
15. What’s your favorite outdoor winter activity?
16. What would your elf name be?
17. Have you ever re-gifted a present? What was it?
18. What is your favorite holiday movie?
19. Have you ever experienced a holiday disaster? What happened?
20. What is the most adventurous thing you have done over the holidays?
21. What holiday thing do you wish would last all year long?
22. What’s that one gift you really wanted when you were younger that you never got?
23. If you could only listen to one holiday song for the rest of your life, what would it be?
24. Who here would build the most creative gingerbread house? How about the most structurally sound?
25. What kind of holiday shopper are you: Black Friday? Christmas Eve? Yearlong hoarder?  Do you wish you were different?
26. If you could invite any famous person, living or deceased, to your holiday celebration, who would it be?
27. Would you rather throw a holiday party or crash one?
28. If you had to live in a holiday movie, which one would you choose?
29. What is your best holiday hack?
30. If you could only buy gifts for others from one store, which would it be?

In the end, holiday gatherings are about more than just festive decorations or elaborate meals. They're about creating a space where memories are made, bonds are strengthened, and family traditions are passed down through generations.  After all, it's these shared moments that weave the rich fabric of our lives and create the stories we'll tell for years to come.

‍

Next up: 11 Creative Ways to Preserve Family Memories – And Pass Them Down