Photo by Ruvim Noga on Unsplash

154 Questions To Ask If You Want to Get To Know Thyself (and Others)

For whenever you’re ready to move past “How Are You?”

I’m a total advocate of icebreaker questions. Sure, they may prompt a few eye-rolls here and there, but they most definitely serve a purpose. Namely, that interesting questions often lead to interesting answers. Plus, using icebreaker questions can help us get out of our normal question-based talking ruts (ie. How are you? How was your day? etc.) and inspire deeper connections.

Below I’ve gathered some of my favorite questions to ask as you’re getting to know someone (or yourself). Consider them pocket-sized guides to small(ish) talk.

Without further adieu…

The Big List of Questions

1. If you had an unlimited supply of anything, what would it be? What would you do with it?
2. What’s something you could talk about for hours, but never get to since no one ever asks?
3. What is something you’re weirdly good at without having had formal training or much practice?
4. What were the first three albums you owned?
5. What was the first movie you saw in a movie theater?
6. What dessert did you always ask for on your birthday when you were a kid?
7. What funky traditions did your family have when you were growing up?
8. What was the best gift you ever received?
9. What was the best gift you ever gave?
10. If you could be anywhere right now, where would you want to be?
11. If you were to create a recipe meant to represent you, what would be the ingredients?
12. Did you think you’d end up where you are now? Why or why not?
13. To date, what’s been the biggest thing that’s surprised you about your life?
14. Would you rather spend an evening alone or out with friends?
15. Have you ever gone to a movie theater by yourself? Did you like it?
16. How often do you think of the past?
17. What’s a mundane memory you’ll never forget— even though it doesn’t hold much importance in your life today?
18. Is there a moment in your life that you wish you could do-over? If yes, what is it and what would you change?
19. Do you believe in heaven or the afterlife? If yes, what does it look like to you?
20. How many people do you consider your true friends?
21. Who is someone special in your life that might not know how special they are in your life?
22. What’s your biggest pet peeve about other people?
23. What’s your biggest pet peeve about yourself?
24. What percentage of the day do you feel like your true self?
25. Who was your childhood crush? Whatever happened to them?
26. When you were a kid, what did you think you would do when you grew up? How close were you?
27. Do you have a sweet tooth or a salty tooth?
28. What was the best meal you ever ate?
29. What’s your favorite meal now?
30. What’s your least favorite food?
31. How often do you speak what’s going on in your mind?
32. When were you the most scared in your life? What happened?
33. Would you ever want to know the time and date of when you were going to die? Why or why not?
34. Do you believe in ghosts?
35. What’s a band you unabashedly love, even if they aren’t necessarily known for being cool?
36. What song(s) do you want to be played at your funeral?
37. 50 years in the future, someone discovers a digital time capsule that includes a Spotify playlist called “The Essence of (Your First Name) (Your Last Name).” What’s the song list?
38. What would you do for your friends or family if money was no issue?
39. What fun fact do you share when asked for a fun fact?
40. What joke do you share when asked for a joke?
41. What was a seemingly small decision that ended up dramatically changing the course of your life?
42. All insecurities and doubts aside, what’s something you genuinely like about yourself?
43. How did you become a better friend?
44. How did you become a better family member?
45. How did you become a better partner?
46. What made you a better human?
47. What’s your favorite personal possession that means absolutely nothing to anyone else?
48. Who is your favorite literary character from a book, movie, or TV show and why?
49. Who is your least favorite literary character from a book, movie, or TV show and why?
50. What’s a food you love in one form, but loathe in another?
51. Based on your physical features, who would be your celebrity parents?
52. What “kid word” do you still use unironically as an adult?
53. What song always makes you feel better?
54. What were you like as a little kid?
55. What were you like as a teenager?
56. At what age do you think you really start to come into your own?
57. How would you finish the sentence: “I wish I could…”?
58. What’s a random factoid you learned in school that you’ll never forget?
59. What’s your best way to turn around an awful mood?
60. What’s the best way to deal with feeling envious of someone?
61. You’re planning your perfect party. What’s the theme, who’s there, what are you eating and drinking, and why is it so uniquely perfect for you?
62. What’s the very best smell in the whole entire world?
63. You’re about to go on stage to perform at a talent show. There’s a 100% guarantee that no one will judge you negatively so you don’t have to worry about embarrassing yourself. What talent do you showcase?
64. What’s something you wished you started doing earlier in your life?
65. What’s something you wished you stopped doing earlier in your life?
66. What small change to your physical appearance made you look like a totally new person?
67. What would be your rockstar name?
68. What would be your superhero name?
69. What are the most important traits you look for in other people?
70. Can someone ever be truly 100% evil?
71. What’s a guilty pleasure you have that you’ve never really told someone else about?
72. Who is your celebrity crush?
73. Where can you usually found at a party?
74. How many cookies can you eat in a single sitting?
75. Do you usually take people’s recommendations? Why or why not?
76. How do you normally show someone you love them?
77. Who do you miss the most right now?
78. If money and prestige were of no importance, what would your career look like?
79. If you were an animal, what animal would you be?
80. If you had to pick between a bagel and a donut, which one would you choose?
81. Given the choice of anyone in the world, who would you want as a dinner guest?
82. Would you ever want to be famous? Why or why not?
83. Do you have a secret hunch about how you will die?
84. If you could change anything about the way you were raised, what would it be?
85. What’s something that took you a really long time to learn?
86. Did you have a pet when you were growing up? If yes, what was its name and what was it like? If no, did you ever want one?
87. If you could wake up tomorrow having gained one quality or ability, what would it be?
88. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?
89. What is the greatest accomplishment of your life?
90. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?
91. When did you last cry in front of another person? By yourself?
92. 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?
93. 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?
94. Would you be willing to have horrible nightmares for a year if you would be rewarded with extraordinary wealth?
95. What risk would you take if you knew you wouldn’t fail?
96. What is your greatest strength? Have any of your recent actions demonstrated this strength?
97. What are your top three most prized possessions?
98. What one piece of advice would you give to your younger self?
99. Do any of the things that used to upset you a few years ago matter at all today?
100. What’s a life pro tip that someone gave you that you’ll never forget?
101. What life lessons did you learn to hard way?
102. Are you a big worrier?
103. If you had one year left to live, what would you do with it?
104. Are you afraid of being your true self around others? Why?
105. Have you done anything you are proud of lately?
106. Have you shown any recent acts of kindness?
107. If you knew that you would die tomorrow, what questions would you ask yourself?
108. What are three words you would use to describe yourself?
109. What are three words a friend would use to describe you?
110. What are three words a partner would use to describe you?
111. What are three words a coworker would use to describe you?
112. What do people often misunderstand about you?
113. Do you tend to take people’s advice?
114. Do you get quickly offended?
115. Would you ever give up your life to save another?
116. If you could live one day over and over again, what would you choose to do?
117. How would the world be different if you had never been born?
118. If your life was a movie, what would the title be?
119. If your life was a movie, what genre would it be?
120. If you could snap your fingers and become a totally different person, would you do it?
121. Who do you look up to most and why?
122. Do the people you love most know how much you love them?
123. What’s something you learned yesterday?
124. What do you like about yourself?
125. Do you really listen when people talk to you?
126. What is the number one change you need to make in your life this year?
127. What are your most common negative thoughts? Are they logical?
128. Do you think it’s too late to do certain things in your life? Why or why not?
129. If you could change anything in the world — big or small — what would you change?
130. What makes life easier?
131. If you had a secret bookcase door to a room in your house — what would be on the other side?
132. If you could send a message to the world, what would you say in 30 seconds?
133. What’s something you regret telling someone
134. What’s something you regret not telling someone?
135. When was the last time you tried something new?
136. Are you afraid to speak your own opinion?
137. What is one mistake that you will never make again?
138. What’s something important to you that you’ve given up on? How do you feel about it?
139. What were you doing the last time you lost track of time?
140. How old would you be if you didn’t know how old you are?
141. When did you last laugh so much it hurt?
142. Should movies be remade? Why or why not?
143. What is one thing you always wanted as a kid but never got?
144. If aliens abducted you one day and said you could choose an entirely new identity for yourself, what name and personality would you give yourself?
145. What’s your favorite potato chip flavor?
146. What’s your favorite ice cream flavor?
147. What’s your favorite cereal?
148. What is one thing you refuse to share with anyone?
149. What always makes you feel more confident?
150. What’s the best concert you’ve ever been to?
151. What is the nicest thing someone else has done for you?
152. What’s the best compliment you’ve ever received?
153. What does an absolutely perfect day look like to you?
154. So what do you reckon — does life get better as you get older?

Sources:

• Pick the Brain
• Buzzle
• Psychology Today
• Friends, family and strangers :)