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101 Fun Questions To Ask Your Future Self In a Letter

A photo of Tom who is the Co-Founder of Questions About Everything

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These questions to ask your future self are perfect if you want to look back in ten, or even twenty years’ time and see how much you’ve changed.

A great way to do this is to write a letter to your future self. You write down several questions, store away the letter and then open it at a predetermined point in the future.

When writing these questions to ask your future self in a letter, it helps to write them in the second person, which is the tense the majority of are questions are in. This creates some distance between you and the future version of yourself, allowing you to critique yourself more thoroughly.

Writing questions to ask yourself in the future is a fun exercise you can do at any age, whether you’re a teenager or you’re in your thirties. Check out our suggestions below and get writing!

Best Questions To Ask Your Future Self

1. What are the biggest regrets you have?

2. What didn’t you spend enough time doing?

3. If you could relive your life up until this point again, what would you do differently?

4. Is there anyone you didn’t thank enough?

5. Did anyone need you more than you realized?

6. Have I become a better person?

7. Is the effort I’m making now worth it in the long run?

8. Are you happy with the way things have turned out?

9. Which people have had my back and which ones haven’t?

10. If you could change one thing about your life in the past ten years, what would it be?

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11. Is there something you wish you had made time for but never got around to?

12. Have you had any health issues that could have been picked up sooner?

13. What’s the best piece of advice you could give me?

14. What’s the most significant scientific breakthrough that’s happened between my age now and yours?

15. Are you still pursuing your dreams?

16. What’s the biggest change between you and me?

17. What personal achievements are you most proud of?

18. What does a typical day look like for you?

19. How much do you earn?

20. What hobbies do you have?

Interesting Questions To Ask Your Future Self

21. Have you been successful in your career?

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22. What are you passionate about?

23. What’s the biggest societal change that’s taken place in your lifetime?

24. If you had to describe yourself in three words, what would they be?

25. What are the biggest things you’ve learnt in life so far?

26. If you had $1 million, what would you do with it?

27. What’s the biggest frustration you have right now?

28. What do you fear the most?

29. Are you living life to its fullest right now?

30. Who inspires you the most?

31. Have things turned out the way you thought they would?

32. Who is/are the most important people in your life right now?

33. What do you miss the most in your life?

34. Has money ever been a pressing issue?

35. Have you ever been seriously ill?

36. Are/were my parents proud of me?

37. Have you passed up opportunities you should have taken up?

38. How much time have you wasted on social media over the years?

39. What does your ideal day look like?

40. Have you ever been let down by someone you trusted?

Deep Questions To Ask Your Future Self

41. Do you wish you were young again?

Next: Unanswerable questions

42. Do you think things have gotten better or worse during your lifetime?

43. Do you have as much purpose now as you did when you were younger?

44. Are you happy with where you’ve ended up?

45. Is there anything you never said to someone that you wish you did?

46. Do you feel like the future you imagined when you were younger has come to fruition?

47. Is the future how it was advertised or has it turned out differently?

48. Has society changed for better or worse during your lifetime?

49. What’s the most significant cultural shift you’ve witnessed in your lifetime?

50. If you had one year left to live, what would you do?

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51. Did you ever make decisions for love that you now regret?

52. Are there any demons you’ve been unable to overcome?

53. What’s the biggest tragedy you’ve had to endure?

54. Do you yearn for the past or are you content with how things are?

55. Are there things you appreciate now you’re older that you didn’t when you were younger?

56. Has life taught you any tough lessons along the way?

57. Are there any fears you haven’t been able to overcome?

58. Has the pace of life slowed down the older you’ve got?

59. Do you feel like things were better ‘back in your day’?

60. What brings you the most joy?

Funny Questions To Ask Yourself In The Future

61. What’s the silliest thing you’ve done?

Next: Funny questions to ask

62. Do you know next week’s lottery numbers?

63. What’s the worst joke you’ve ever said?

64. What’s the funniest thing that’s happened to you?

65. Have you gotten funnier as you’ve become older?

66. Have you stopped having wild nights out or not?

67. Are you a boring old man/woman or are you still having a lot of fun?

68. What’s the best joke you’ve heard down the years?

69. Do you still call Mom if you can’t find something?

70. What’s the value of the stock I bought back in 2020?

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71. Do you shower more or less now that you’re older?

72. Have you ever witnessed something so funny, that it hurt when you laughed?

73. Has a robot been sent from the future to terminate you yet?

74. What’s your most embarrassing moment?

75. Do your friends still make you laugh like they used to?

76. What’s the biggest fashion faux pas you’ve ever made?

77. What’s the worst fashion trend you followed that makes you cringe now?

78. Is there a hairstyle you regret getting?

79. Do you have any funny drunken stories that make you laugh?

80. What’s your funniest dating story?

Random Questions To Ask Your Future Self

81. How many countries have you visited?

Next: Critical thinking questions

82. What’s the first thing you do when get up in the morning?

83. What’s the most prized possession you currently own?

84. What’s the biggest failure you’ve had?

85. Has your purpose in life changed at any point? What caused it to change?

86. How regularly do you donate to charity? Which ones do you donate to and why?

87. Have you had a near-death experience?

88. Have you saved somebody’s life? If so, what happened?

89. Did you find someone to settle down with?

90. Are you happy?

91. What’s your favorite activity you’ve taken up as you’ve become older?

92. Are you a good parent?

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93. What’s one aspect of my life I should work on improving as a priority?

94. What’s your favorite place to hang out?

95. What’s your favorite way to relax now you’re older?

96. Who makes you smile the most?

97. Have you committed a crime? If so, what happened?

98. What’s the weirdest thing you’ve done that I’ll struggle to believe?

99. Is there anything you’ve done that surprised you?

100. Have your preferences in food changed over time or not?

101. What things have you excluded from your life?

Looking For More Questions?

Questions to ask a mentee – If you’re mentoring someone, this is a helpful set of talking points you can use to get them engaged.

Hardest questions to answer – A tough set of questions that will have you pondering long and hard about the answers.

Philosophical questions – Consider some fascinating talking points with these philosophy-based questions.

Existential questions – Ponder some talking points that will bend your mind!

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.