The 25 Best Conversation Starters for Holidays 2021

The 25 Best Conversation Starters for Holidays 2021

The holidays are all about family, everybody knows that. But even so, sometimes it can be hard to think of things to talk about, especially if you haven't seen some of these people for a very long time. 

But have no fear! We have some pretty outrageous conversation starters below that are perfect for breaking the ice and making any holiday family function totally bearable.

If you like the ones below, don't forget to check out our 141 Outrageous Conversation Starters for Couples card deck for even more hilarious conversations!

Check out the card deck!

25 Outrageous Conversation Starters for the Holidays

1. You are given unlimited funds to build your dream house, but it must be made entirely out of graham crackers and candy. To top it off, you can only use three different types of candy on your house. Which candies do you use to build your decadent dream house and why? 

2. Your family is pitching in to get you the most awesome gift this year! But, they say it has to be completely impractical and way over the top. Given a budget of $10,000, what five ideas would you put on your wishlist, knowing you’ll only receive one thing?

3. Who is the most interesting person you met this last year? How did you meet them and what made them so interesting?

4. What is the absolute best idea you had this year? How did you come up with that idea?

5. Think back on the year. What are the three most dangerous or scariest moments that you were a part of?

6. Describe your year using three colors, three places, and three foods only.

7. If you were creating a scrapbook containing all the most memorable moments of this year, what five events would you choose?

8. You make Santa fall off his ladder, inheriting his role. Your first duty is to rename all nine reindeer. What new names would you choose?

9. What are the three most exciting things that happened to you this year? If they didn’t happen, how do you think that might have changed your life?

10. What ten words come to mind when you think of the holidays?

11. What does the perfect holiday season look like to you? If money, time, and responsibility were no issue, how would you plan your next holiday season?

12. What is a holiday shopping fail you’ve experienced in your life?

13. If you had to spend December with only three people, which three people would you choose and why?

14. If you were ten years old today, what five things would you add to your holiday wishlist?

15. What one holiday dessert would you magically change to be calorie-free?

16. If you were given $500,000 dollars to donate this year, but had to choose ten different people or organizations to give it to, who would you choose and why?

17. If forced to eat/drink it every day, which one of the following would you choose (and which would be last on the list): Eggnog, cranberry sauce, fruit cake, or sweet potatoes.

18. Which person in the family do you think is the best shopper? Who is the best wrapper? Who is the best holiday chef? Who is the most organized? Who is most family-oriented?

19. If you were Santa and could replace reindeer with another type of magical flying animal, what would you choose and why?

20. Who would you most likely choose to be turned into a snowman?

21. Thinking back on the year, what are the eight craziest nights you can think of?

22. You are a visionary and a one-of-a-kind type of person. Instead of the traditional evergreen fir, what type of tree would YOU bring into the house to decorate?

23. You are the top real estate agent in the world. Santa calls you up and says that they are thinking of relocating the workshop to another part of the world. What three countries do you suggest and why?

24. What are you looking forward to most in the next year?

25. Name five people that you are most thankful to have in your life this year who are not a part of your family.

Looking for more crazy conversations?

Click below to get our 141 Outrageous Conversations Starters for Couples card deck and get ready for some major laughs with the family!

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