Xizhen’s curated list of 100 questions that has grown way longer than 100 questions

  1. Which of the seven deadly sins do you identify with the most?
  2. How different would you envision yourself if you were born as the opposite gender?
  3. If you were a fruit what fruit what you be?
  4. What’s your happiest childhood memory?
  5. What do your friends do that make you happy?
  6. What do your friends and family do that make you unhappy?
  7. What are three of the best compliments you think you can receive?
  8. How do you imagine your ideal adult life?
  9. What was your dream job as a kid?
  10. Spot the duo in the trio (eg neapolitan flavors)?
  11. Which of the my little pony mane six do you identify with the most? And why?
  12. Who in your life makes you feel most like yourself? Or who can you be yourself the most around?
  13. What do you wish people asked you more?
  14. What do you do that makes you feel most like yourself? Like what is your trademark action
  15. given a word, do you think it’s more tragical or comical?
  16. What’s an abstract thing you want very badly?
  17. What do you think people misunderstand about you?
  18. If you wanted someone to understand you on a deeper level what would you tell them?
  19. What’s your favourite word?
  20. If you did a Ted talk what would it be about?
  21. What’s your favourite thing about living right now?
  22. What would you do if you had no inhibitions?
  23. What are some things you did in the past that you no longer do now, or something you didn’t do in the past that you do now?
  24. How would you want your friends and family to describe you to someone you don’t know?
  25. What’s your favourite physical sensation?
  26. What’s your top out of the five senses?
  27. Trolley problem?
  28. Favourite word from letters a-b?
  29. Seemingly ordinary things you’re obsessed with/interested in?
  30. Recurring dream/nightmare?
  31. Radical opinions?
  32. Something that irrationally irks you. A pet peeve, so to say?
  33. What’s your favourite scent?
  34. If you were an ice cream flavour what would it be?
  35. Antonyms?
  36. given 3 random objects, which one is the most x(t)/v(t)/a(t)
  37. When’s the last time you crashed out?
  38. When’s the last time you felt extremely nervous?
  39. What’s a quality you dislike in a person you admire most?
  40. If you could erase one thing from your memory what would it be?
  41. What’s the hardest lesson you’ve learnt?
  42. What’s the biggest change of heart you’ve had?
  43. Some historical figures have epithets attached to their names, like The Mad or The Wise. What would you like yours to be?
  44. If you could change one thing about yourself physically, what would you change?
  45. Summarise your life in one sentence
  46. what’s the best advice you’ve received
  47. You have one year left to live, what would you do
  48. Scariest moment of your life thus far?
  49. Greatest physical pain you’ve felt
  50. What trait do you admire most
  51. Who has had the most positive impact on your life?
  52. If you were an inanimate object, what would you be and why
  53. If you could be good at any profession without having to receive the accompanying education or trade experience, which would you choose
  54. Is there a song/movie/food/etc. that strongly reminds you of someone whenever you experience it? Who does it remind you of?
  55. What cliché do you think is bullshit? What cliché do you think holds truth?
  56. What is your ideal birthday? Not the date, but rather your ideal way to spend the day
  57. What’s the worst advice you’ve ever been given
  58. What is the most important quality you look for in a friend? A romantic partner?
  59. What do you get the most compliments about?
  60. Which of your flaws are you most ashamed of?
  61. What was the hardest decision you’ve ever made?
  62. What is something you never thought you’d be able to do, until you actually did it?
  63. What is something you don’t realize is weird until you really think about it?
  64. Can you tell me a joke
  65. Is there something you wish everybody knew about you without you having to tell them?
  66. What would be the most you’re willing to sacrifice for love
  67. What question do you most hate being asked?
  68. What’s your favorite article of clothing you own? Where did you get it? How long have you had it?
  69. What’s something you wish you enjoyed but never can seem to?
  70. Have you ever challenged or questioned a belief you held for a long time? What prompted it and what was the result?
  71. Think of your biggest regret. If you could go back in time and make a decision to keep it from happening, would you?
  72. What’s the craziest thing you’ve ever done?
  73. Have you gone through any phases in your life? What is the most notable one?
  74. Would you prefer your family to be smaller or larger than it is now, or neither? Do you wish you were more involved with your extended family?
  75. What is something you’re hypocritical about; something you believe but have a hard time sticking to in practice?
  76. Core memories
  77. When you’re sick, what are some things you eat/drink/watch/etc. to be comfortable?
  78. What are some core principles you have that you’ll never give up or change?
  79. What cause do you strongly support, even though it wouldn’t directly benefit you?
  80. What is something weird you do that you wonder if other people do as well?
  81. What is one thing you’re good at that people don’t expect?
  82. Do you suffer from imposter syndrome?
  83. How do you differ from your parents?
  84. What stereotype are you most like?
  85. What is something you want but will never have?
  86. What is something that’s difficult for you but easy for most others? Etc
  87. What character trait instantly makes you respect someone?
  88. What’s the most selfish thing you’ve done?
  89. What’s the most selfless thing you’ve done?
  90. What is your least favorite question to answer?
  91. What about yourself is completely different from what you were like 10 years ago?
  92. If you died today, what would be your biggest regret?
  93. What wouldn’t you do for someone you love?
  94. What is a completely rational, justified fear that you have?
  95. What is something you love that most people hate? Vice versa?
  96. What is something you and I disagree on?
  97. When do you feel like the best version of yourself?
  98. Have you ever been unable to sleep? Why?
  99. If you opened a restaurant, what would you name it, and what cuisine would you serve? What would the atmosphere be like?
  100. What’s the most beautiful view you’ve ever seen?
  101. What is the best thing that happened to you this week?
  102. What’s the strangest situation you’ve ever found yourself in?
  103. What’s the quickest way to get you angry?
  104. How would you want your children’s childhoods to be different from your own?
  105. Have you discovered anything about yourself in the past year?
  106. Who could you listen to for hours? It can be someone you know or someone you don’t.
  107. What immediately makes you think less of someone? Vice versa
  108. Have you ever cried in public? If so, was the reason?
  109. Is there anyone you envy? What is it about them that you envy? If not, what is something people might envy you for?
  110. Have you ever written a thank-you note to someone who created or helped create something you enjoy? If not, who would you write to and what would you thank them for?
  111. What is something you love, but can’t recommend to your friends/loved ones because you know they won’t like it?
  112. Is there someone you knew once but have lost touch with? What happened? Do you know where they are now?
  113. What is your catchphrase, or something you find yourself saying often?
  114. Do you have gut feelings
  115. Have you ever hit “rock bottom”? What did it look and feel like to you? What situations or decisions led to it? How did you get out, or have you gotten out yet?
  116. When was the last time you did something nice for someone completely unprompted?
  117. What is the first thing you hope people notice about you?
  118. What is something you’re embarrassed to admit you enjoy? Why are you embarrassed about it?
  119. What is something you fantasize about often?
  120. Is there something you want to tell someone, but haven’t? Why haven’t you done it, and how do you think they would react if you told them?
  121. What person in your life would you most want to be stuck in an elevator with for 24 hours?
  122. What is something you enjoyed doing but would never do again?
  123. Object that defines who you are
  124. Under what circumstances do you think you could kill someone, if any?
  125. What do you think is worth dying for, if anything? 
  126. What is the most dangerous thing you’ve ever done, and why did you do it? 
  127. Have you ever gotten a “hunch” about something that turned out to be true?
  128. What is something you know is going to happen, but hasn’t yet?
  129. What do you wish you remembered better?
  130. Someone you love will die at the end of today. Only you know this; they don’t. How do you spend your last day with them and when do you tell them that they’re going to die, if ever? 
  131. Without using name, ethnicity, race, gender, religion, species, age, sexual orientation, material you are made from, what are you?
  132. What’s the kindest lie you’ve ever told someone?
  133. What’s a habit of yours?
  134. Would you rather be loved or understood?
  135. Marry someone you don’t love or marry someone who doesn’t love you?
  136. Be with an obsessive person or a nonchalant person?
  137. What do you think of obsession?
  138. What is a fear you’ve faced and how did you face it?