50 Interesting Questions to Spark Meaningful and Fun Conversations

The holidays are looking a little different in 2021. Amid a global pandemic, we’re coming to terms with smaller-scale lunches in more intimate settings with merely our closest family and friends, which is nice, albeit a little daunting in the conversation department.

Because after a weird year, it’s natural we may have less to talk about. Your usual repertoire of questions about work and travel plans likely won’t cut it to spark those deep and meaningful conversations, and so we at The Latch have compiled the ultimate list of interesting questions to ask your friends and family.

1. How are you? No, really, how are you actually doing?

2. What are you most looking forward to experiencing in the next five years?

3. What happened in your life that has defined the last five years?

4. When was the last time you helped someone and what did you do for them?

5. What is your measure or definition of success?

6. Are you a Kim, Kourtney, Khloe, Kendall or Kylie?

7. Are you team Friends or team Seinfeld?

8. When was the last time you paid it forward?

9. Dead or alive, who would be your ultimate dinner party guests?

10. Which item, aside from loved ones, would you save in a house fire?

11. What’s one thing you wish people would talk about less and what’s one thing you wished people spoke more about?

12. Would you like to be famous? If so, what for and why/why not?

13. Do you ever have conversations with yourself or rehearse important chats?

14. What song do you wish you could sing to absolute perfection?

15. Which parts of your life are you most grateful for?

16. Would you rather be able to speak every language or speak to animals? Why?

17. What’s one project you’ve always wanted to undertake? Why haven’t you done it yet?

18. What qualities do you most value in a friend and lover?

19. What’s a memory you would like to relive?

20. Can you describe your perfect final meal in excruciating detail? 

21. Describe a silly and made-up game you used to play as a child.

22. Where in the world would you teleport to right now? What would you be doing there?

23. Where is the most beautiful place you’ve ever seen?

24. What is your favourite part of your own personality?

25. What is the most precious thing you own?

26. Which TV show would you happily insert yourself in?

27. What did you learn about yourself from your last relationship?

28. What part of yourself are you currently working to improve?

29. Which lost hobbies would you like to pick up again?

30. Which song have you been playing on repeat for years? 

31. What would your younger self not believe about your life today? 

32. Who was your favourite teacher in school, and why did you like them?

33. If you could drop in on another time period, which era would you choose?

34. What is the nicest thing anyone has ever said about you?

35. Do you like your name? What name would you choose for yourself as an alternative?

36. What do you see as your career after this one?

37. Which of your friends would you most like to be like? Why?

38. Tell me about a stranger that made a lasting impression on you.

39. If you could ask your pet one question and have them answer, what would it be? 

40. Which of your favourite movies deserves a sequel?

41. Has a book ever changed your life? Why?

42.  If you could shop for free at one store for the rest of your life, which store would you choose?

43. Which world city would you choose to live in and why?

44. What would your dream home look like? Describe it to me.

45. What is your favourite thing about the internet today? 

46. What is something you wish people would stop doing? 

47. What is one story you’d be excited to tell your children one day?

48. If you could have any magic power, what would it be?

49. Which TV or movie character would you have as your roommate?

50. What is the most recent lie you have told? 

Got a suggestion for an interesting question? Should we bulk this out to a full 100? Slide into our DMs on Instagram and let us know of a killer conversation starter.

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