Meaningful Questions

Small talk is great. Even greater is meaningful talk. How? Just ask meaningful questions. You will surely stand out by asking these:

1. If you could go back in time and change one thing, and one thing only, what would you change?;
2. Who is your favourite person, and why is it me?;
3. What is your first memory?;
4. What will people say on your funeral? What do you want them to say?;
5. If you didn’t need to work for money, what would you like to do?;
6. What is your favourite song/book/movie? Why? What did you get out of it?;
7. What products do you absolutely recommend?;
8. What are some things you didn’t do but wish you had done?;
9. If you could ask anyone 1 question and have him/her answer truthfully, what and whom would you ask?;
10. What is one thing (or several) that you wish you had started/done sooner?;
11. If you could ask an all-knowing being (some god) 1 question and have him/her/it answer truthfully, what would you ask?;
12. What do you think stands between you and complete happiness?;
13. If you were to win 1M (or 5M or however much), what would you do with the money?;
14. How would you design/build your perfect home/apartment-complex/room/city?;
15. What will the present punish you for?;
16. What will the future punish you for?;
17. What are your favourite purchases of the last X years?;
18. Rock bottom. What happened, when, why and what did you learn?;
19. What are some things you are excited about?;
20. What are you afraid of?;
21. If you could have a gigantic billboard anywhere with anything on it - reaching millions or billions of people - what would it say and why?¹;
22. What is an unusual habit of yours that you recommend?¹;
23. What is your favourite failure (or apparent failure) that set you up for future success? What happened?¹ (This is similar to question 18.);
24. What new belief, behavior or habit has improved your life the most in the last five years?¹;
25. What would you do if you were stuck in a time-loop, that is, you were constantly reliving the same hour/day/week/year?;
26. What is the origin of your suffering?;
27. What do you want but don’t have?;
28. If you could press a button and then have all of your wants fulfilled, to such a rapid degree that you don’t experience the want, would you? That is, as the want arises, it is fulfilled immediately. Would you press the button?²;
29. What do you think of free will?;
30. How do you see yourself making a positive impact on the world around you?;
31. What are some of your greatest strengths and weaknesses, and how do they impact your life and relationships?;
32. What brings you the most joy and fulfillment?;
33. What do you think is the purpose of life?;
34. What do you think is the biggest problem facing society today?;
35. What do you think is the most important quality for a person to possess, and why?;
36. What are some hacks that you employ to improve your life?;
37. What is your identity?;
38. What are some unfulfilled things in your life?;
39. How have you changed in the past year?;
40. What are some small things people do that you really enjoy? What specific acts of kindness?;
41. At what point in your life have you had the highest self-esteem?;
42. Do the opinions of others affect you? How so?;
43. Do you miss somebody? Who?;

The following questions are the so called “36-questions” (from 44 to 79) by Arthur Aron and Elaine Aron. Some of them are not really questions though.

44. Given the choice of anyone in the world, whom would you want as a dinner guest?;
45. Would you like to be famous? In what way?;
46. Before making a telephone call, do you ever rehearse what you are going to say? Why?;
47. What would constitute a “perfect” day for you?;
48. When did you last sing to yourself? To someone else?;
49. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?;
50. Do you have a secret hunch about how you will die?;
51. Name three things you and your partner appear to have in common.;
52. For what in your life do you feel most grateful?;
53. If you could change anything about the way you were raised, what would it be?;
54. Take four minutes and tell your partner your life story in as much detail as possible.;
55. If you could wake up tomorrow having gained any one quality or ability, what would it be?;
56. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?;
57. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?;
58. What is the greatest accomplishment of your life?;
59. What do you value most in a friendship?;
60. What is your most treasured memory?;
61. What is your most terrible memory?;
62. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?;
63. What does friendship mean to you?;
64. What roles do love and affection play in your life?;
65. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.;
66. How close and warm is your family? Do you feel your childhood was happier than most other people’s?;
67. How do you feel about your relationship with your mother?;
68. Make three true “we” statements each. For instance, “We are both in this room feeling…”;
69. Complete this sentence: “I wish I had someone with whom I could share…”;
70. If you were going to become a close friend with your partner, please share what would be important for him or her to know.;
71. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.;
72. Share with your partner an embarrassing moment in your life.;
73. When did you last cry in front of another person? By yourself?;
74. Tell your partner something that you like about them already.;
75. What, if anything, is too serious to be joked about?;
76. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?;
77. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?;
78. Of all the people in your family, whose death would you find most disturbing? Why?;
79. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect to you how you seem to be feeling about the problem you have chosen.;

The “36 questions” end here. There is more however!

80. Do you like who you are right now?;
81. When was the last time you laughed really hard?;
82. What would you do if your biggest fear came true?;
83. Are you afraid of being your true self (and/or true to yourself) when others are around?;
84. What aspect of your personality still needs improvement?;
85. What belief do you have that most people disagree with?;
86. Who are your top 3 role models?;
87. What are you complimented for, usually?;
88. How do you fill the emptiness?;
89. What is your goal? Personally, career-wise, etc;
90. What do you stand for? What are your beliefs?;
91. What does a successful person mean to you?;
92. What is holding you back?;
93. What do you want to achieve in the next 3/6 months?;
94. What are some changeable attributes that you find interesting/attractive?;
95. What are some before-and-after experiences/moments/events/decisions of your life?;
96. Imagine you are a parent and you have a child aged X years. Your child has gone through time travel of sorts, to the future or past. He is unavailable. However the future version of your child (aged X + Y years) visits you. Do you love the future version of your child just the same? Do you miss the younger child? Are these feelings true for all values of X and Y?;

These are some of the questions I like to ask people (and myself, when I am in an introspective mood). Some of these are my own but most are taken from multiple places for which I have no source, i.e., I stole them.

If you have any additional question that would fit this list, please e-mail me (hi at miguelmf.com).