A Christmas Without Small Talk

30 questions to bring real connection back to the table.

The holidays are here and I don’t know about you, but with certain relatives I find myself having the same surface-level conversations every year. And I’ve finally realized that real connection doesn’t happen accidentally, it has to be created.

So I put together a handful of questions you can sprinkle into your family gatherings this week. Some are light, while some go deeper, all designed to make conversations more fun and help us learn something about each other. 😉

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1. If you were an elf, what would your job in Santa’s workshop be?

2. What’s the biggest lesson you learned in college?

3. What should everyone do at least once in their lives?

4. What makes you write someone off?

5. What is your favorite toy or Christmas gift from childhood?

6. When do you feel truly “alive”?

7. If you could only eat one dessert for the rest of your life, what would it be?

8. What has been the biggest change you ever made that made you the most proud of yourself?

9. If you could only have potatoes one way for the rest of your life, how would you havethem prepared / what is your favorite potato?

10. What is your most cherished childhood memory?

11. Do you have a favorite family tradition?

12. Who is someone who has made you the person you are today but who has no idea oftheir impact?

13. What’s something that you love but that you don’t like to buy for yourself because youview it as unnecessary?

14. If you knew success was a certainty, what would you do?

15. When did you find out about Santa? (Careful, if the kiddos are around 🎅🏽)

16. If you could broadcast one message to the world for everyone to hear, what would itbe?

17. Would you rather receive a phone call or a handwritten note?

18. What is the best thing that someone could say to you?

19. Who would you want to be stuck in an elevator with and why?

20. What did you think you were gonna be when you grew up?

21. If you had a podcast, what would you talk about?

22. What’s the best book you ever read? Why?

23. What could you give a 40-minute presentation on with zero preparation?

24. If you could go back and be a professional in any sport, which sport would you choose?

25. Would you rather be very intelligent and have no common sense or have ample common sense and no book smarts?

26. If you won the lottery, what are the first 5 things you would do with it?

27. What is your favorite type of cheese?

28. If you had one month off work, paid, what would you do with your time?

29. If you could learn everything about 1 topic in a day, what would it be?

30. What’s one goal you have for 2026?

Fun-tip: Make this into a game by asking people to pick a number from 1-30, and then ask the question that matches.

xx.

Andi