Curated Questions

Overview

Here's our list of meticulously curated questions that we've collected over years of throwing meaningful events to ask over dinner for conversation that is real, alive and profoundly connecting. We recommend asking each person to pick a number from 1-68 and then reading that question out for them to answer to the group.

1. What’s the most common thing that you are jealous of in other people?

2. If you could go back in time and tell your 12 year old self one thing, what would you tell them?

3. What’s the first in your life and the last thing in your life that shocked you?

4. How much do your parents influence your decisions?

5. Why would you date yourself, why would you not?

6. What do you absolutely know you’re good at?

7. If this was as good as it’s going to get, how would you feel?

8. What are the common themes in the people you are closest to?

9. How do you know if you’ve had a good day?

10. If you could smash open a piñata and anything could be inside, (literal or abstract) what would it be and why?

11. What’s been the best year of your life and why?

12. Give each person in the group a sincere compliment

13. What’s the thing your parents are most proud of you for?

14. When’s the last time you felt lonely?

15.What are you hoping for from today? (What is your ideal outcome)

16. If you really knew me you would know that…

17. What happens after we die?

18. What is your Achilles Heel, (what is your weakness)?

19. Looking back on your deathbed, what does a successful life look like for you?

20. If you could make people feel anything in your presence, what would it be?

21. What gets you up in the morning? (Figuratively rather than literally)

22. How does Man end? (The human race)

23. What do you hope people don’t notice about you today?

24. What’s the most you’ve ever loved someone?

25. Describe your perfect Sunday from when you wake up to when you go to sleep if money were no object

26. What about you do you think would make you a great parent?

27. What do you do when trying to make someone fall in love with you?

28. What do you do now that you wouldn’t want your kids / nephews / nieces / grandchildren doing?

29. What do you find it hard to share? (Feel free to interpret as emotional or literal)

30. What’s the best date that anyone could take you on?

31. What are you most excited for in the 2030s?

32. How could I put you most at ease right now?

33. What do you think is the main reason to be in a relationship instead of single?

34. If you could change one thing about your body, what would it be?

35. What makes you feel the most content?

36. If it wasn’t bad for you, what would you do as much as you wanted?

37. What keeps you up at night when you can’t sleep?

38. What personal growth are you aware that you haven’t done yet and you’re trying to do right now?

39. What would you do if you weren’t afraid?

40. What do you like to show off whenever you get the chance?

41. Rate the following areas of your life out of 10 and explain their rating: 1) Love life. 2) Social life. 3) Family relationships. 4) Work / equivalent if retired / unemployed. 5) Home / habitat.

42. If you had a magic carpet and it could take you anywhere for 5 hours, where would it take you right now?

43. What’s wrong with you?

44. What are the things about you that you imagine society deems is positive and negative?

45. If you had a button on your arm that could do anything to your body or mind for 30 mins every time you press it, what would it be?

46. When’s the last time you were deeply nervous?

47. If you knew you were going to get everything you ever wanted in every single imaginable area of your life in one year’s time, and nothing you could do would increase or decrease the chances of it happening, how would you live your life differently? (I.e. rather than thinking about what you want, the question essentially asks how do you pass the time when you’re not working toward anything).

48. If you lived in the opposite sex’s body, how would you dress and what would your style be?

49. What’s the earliest present you remember loving?

50. What’s a sliding doors moment where there could’ve been a different future in your life?

51. What’s the first time you remember making a real friend and what was the moment that you realized you were friends?

52. What 5 things if you lost this morning would you definitely have purchased again by this evening. You aren’t allowed to pick your toothbrush, phone, laptop, or charging devices.

53. If you could relive one memory, not changing it in any way, just experiencing it, which one would you relive?

54. If you could control one person absolutely for 6 months, who would you control?

55. If you had the choice, how would you like to die?

56. If you had to have kids with any of your ex’s, who would you pick?

57. What are the top 3 things you think about over and over again in a day?

58. What is a moment in your life when you knew in the moment itself that you were growing up?

59. What are 3 things you couldn’t be happy without?

60. What do you want to be remembered for? Based on what you’ve done and what you’ve achieved, what do you think you’ll actually be remembered for?

61. If you had a Men in Black neuralizer, (memory erasing device) what one thing would you do and then remove people’s memories of?

62. If you had to raise a child, name one thing you'd do differently to your parents?

63. Name something that you did in the last year which made you truly happy

64. What has been your biggest failing at work or on a project you cared about?

65. Have you ever nearly died?

66. If you could be the best at anything in the world, what would it be?

67. What were the top 5 songs on your Spotify wrapped last year?

68. What is your condition of worth? (The thing you do that earns your place in a group)