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175 Deep Questions

Updated: Jul 11



  1. Do you want children? If yes/no, why?

  2. What are you most proud of the past year?

  3. What are three things you are grateful for?

  4. What makes you come alive?

  5. What could you do today that would improve your life?

  6. What would you tell you 5 years younger self?

  7. What is a recent compliment you have given someone?

  8. What qualities do you admire most in people?

  9. What should be compulsory learning in schools?

  10. What should you do more for?

  11. How would your best friend describe you?

  12. What is the craziest thing you have ever done?

  13. Describe a strength and a weakness that you have

  14. Are you an introvert or extrovert?

  15. Who is the person you are closest to?

  16. What is a deal breaker in a relationship for you?

  17. What did you past relationship teach you?

  18. If a genie granted you 2 wishes what would you ask for?

  19. Does your job make you happy?

  20. What is a spontaneous thing you have done recently?

  21. What’s one thing you wish you knew how to do?

  22. Do you have an irrational fear of anything?

  23. What does happiness mean to you?

  24. Do you consider that you have a life purpose? If so what is it?

  25. If you didn’t have to sleep, what would you do with the extra time?

  26. What hobby would you get into if time and money weren’t an issue?

  27. What would your perfect house look like?

  28. When was the last time you climbed a tree?

  29. What skill would you like to master?

  30. What would be the most amazing adventure to go on?

  31. If you had unlimited funds to build a house that you would live in for the rest of your life, what would the finished house be like?

  32. What town or country do you never want to go back to?

  33. Are you usually early or late?

  34. What takes up too much of your time?

  35. What do you wish you knew more about?

  36. What would be your first question after waking up from being cryogenically frozen for 100 years?

  37. What are some small things that make your day better?

  38. Who’s your go to band or artist when you can’t decide on something to listen to?

  39. Who has impressed you most with what they’ve accomplished?

  40. What age do you wish you could permanently be?

  41. What would be your ideal way to spend the weekend?

  42. What’s something you like to do the old-fashioned way?

  43. What have you only recently formed an opinion about?

  44. What are you interested in that most people haven’t heard of?

  45. How do you relax after a hard day of work?

  46. What was the best book or series that you’ve ever read?

  47. What’s the farthest you’ve ever been from home?

  48. What is the most heart-warming thing you’ve ever seen?

  49. What is the most annoying question that people ask you?

  50. What could you give a 40-minute presentation on with absolutely no preparation?

  51. If you were dictator of a small island nation, what crazy dictator stuff would you do?

  52. What is something you think everyone should do at least once in their lives?

  53. Would you rather go hang gliding or white water rafting?

  54. What’s your dream car?

  55. What’s worth spending more on to get the best?

  56. What is something that people are obsessed with but you just don’t get the point of?

  57. What are you most looking forward to in the next 10 years?

  58. Where is the most interesting place you’ve been?

  59. What’s something you’ve been meaning to try but just haven’t gotten around to it?

  60. What’s the best thing that happened to you last week?

  61. If all jobs had the same pay and hours, what job would you like to have?

  62. How different was your life one year ago?

  63. What’s the best way to start the day?

  64. What quirks do you have?

  65. What city would you most like to live in?

  66. What movie title best describes your life?

  67. Why did you decide to do the work you are doing now?

  68. What’s the best way a person can spend their time?

  69. What is the luckiest thing that has happened to you?

  70. Where would you rather be from?

  71. What are some things you’ve had to unlearn?

  72. What are you looking forward to in the coming months?

  73. Where do you usually go when you when you have time off?

  74. Where would you spend all your time if you could?

  75. What age do you want to live to?

  76. What are you most likely to become famous for?

  77. What are you absolutely determined to do?

  78. What is the most impressive thing you know how to do?

  79. What are you absolutely determined to do?

  80. What is the most impressive thing you know how to do?

  81. What do you wish you knew more about?

  82. What question would you most like to know the answer to?

  83. What question can you ask to find out the most about a person?

  84. When was the last time you changed your opinion / belief about something major?

  85. What was the best compliment you’ve received?

  86. As the only human left on Earth, what would you do?

  87. Who inspires you to be better?

  88. What do you spend the most time thinking about?

  89. If you could make one rule that everyone had to follow, what rule would you make?

  90. What are you addicted to?

  91. What stereotype do you completely live up to?

  92. What is something you can never seem to finish?

  93. What would you do if you knew you were going to die in one hour?

  94. What book impacted you the most?

  95. Who is / was your most interesting friend?

  96. Have you ever given to any charities?

  97. What is something that your friends would consider “so you”?

  98. What risks are worth taking?

  99. What can you not get right, no matter how many times you try?

  100. If you could convince everyone in the world to do one thing at one point in time, what would that thing be?

100. What do you take for granted?

101. What would be some of the most annoying things about having yourself as a roommate?

102. What’s something you are self-conscious about?

103. What personality trait do you value most and which do you dislike the most?

104. What small gesture from a stranger made a big impact on you?

105. What challenging thing are you working through these days?

106. What irrational fear do you have?

107. If you had a clock that would countdown to any one event of your choosing, what event would you want it to countdown to?

108. What makes a good life?

109. What’s the last adventure you went on?

110. When do you feel truly alive?

111. Who is a saviour in your life?

112. What are three interesting facts about you?

113.Which of your scars has the best story behind it?

114. What’s the title of the current chapter of your life?

115. What’s the hardest lesson you’ve learned?

116. When people look at you, what do you think they see / think?

117. What have you created that you are most proud of?

118. What bends your mind every time you think about it?

119. What’s the best thing you got from your parents?

120. What are the top three things you want to accomplish before you die? How close are you to accomplishing them?

121. What is the biggest lesson you never learned?

122. What lifestyle change have you been meaning to make for a while now?

123. What chance encounter changed your life forever?

124. How do you hope you’ll change as a person in the future?

125. What do you regret not doing?

126. What gives your life meaning?

127. How do you get in the way of your own success?

128. What’s one thing you did that you really wish you could go back and undo?

129. What are you afraid people see when they look at you?



130. What have you been thinking about lately that interests you?

131. Why do you think having deep conversations is good?

132. Which super power would you rather have?

133. Do you think wealth can make you happy?

134. What would you love to do that you've never tried?

135. What single event has had the biggest impact on who you are?

136. What lies do you most often tell yourself?

137. Are you a spiritual person?

138. What’s the hardest thing you’ve been through?

139. What age do you feel on the inside? Why?

140. Describe ‘freedom’ in your own words?

141. What is the next big step you need to take?

142. Other than money, what else have you gained from your current job?

143. What do you think is more important: exploring the world or exploring yourself?

144. What’s one thing you would change about yourself?

145. What totally impresses you?

146. What are three things that make you happy instantly?

147. What’s your number one goal in the next 6 months?

148. Would you rather have an epic, tragic romance or a satisfying long-term relationship?

149. Do you live more in the moment or plan for the future?

150. What are you most afraid of losing?

151. What do you value most in friendship?

152. Would you rather travel to another planet or the bottom of the ocean?

153. Would you take your boss’ job if it was offered to you?

154. Would you rather be twice as smart or twice as happy?

155. What emotion do you experience most?

156. Do you think you’re brave?

157. What is more important to you – power, money or status?

158. Where would you like to be in 5 years?

159. Are you more into looks or brains?

160. Are you confrontational?

161. What are you most thankful for?

162. Do you believe everything happens for a reason?

163. If you could not work for a year, what would you do?

164. Have you ever performed in front of a crowd? If so, what did you do?

166. When was the last time you turned your phone off?

168. Have your priorities changed over time?

169. Is there anything you’re ashamed of in the past?

170. If you won the lottery what would you do?

171. If you lost your job tomorrow how long would you be able to survive?

172. Are you close to your parents?

173. What were your initial thoughts about me?

174. Who is the most important person in your life?

175. What is a dream you are too scared of admitting?



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