Questions to ask your friends

Fun questions to ask your friends

1. What's something you're into right now that you could talk about for an hour? Then ask What got you started?
2. What did you want to be when you were 10? Then ask How close did you get?
3. What's a place you'd go back to tomorrow if you could? Then ask What would you do first?
4. What's a small thing that made your week better? Then ask Does that happen often?
5. What's a skill you'd learn if time and money didn't matter? Then ask What's the first thing you'd do with it?
6. What's the best thing you've eaten in the last month? Then ask Where was it?
7. What's your order at the café you go to most? Then ask What would make you try something else?
8. What's a song you never skip? Then ask When did you first hear it?
9. What's the most useful thing you own that cost almost nothing? Then ask How did you end up with it?
10. If you could live in any neighborhood in your city, which would it be? Then ask What would your first weekend there look like?
11. What's a hobby you picked up and dropped within a month? Then ask What made you stop?
12. What does your ideal Sunday look like, start to finish? Then ask When did you last have one?
13. What's a show you've rewatched more than twice? Then ask What keeps you coming back?
14. What's the most interesting job you've ever had, even for a week? Then ask Would you go back to it?
15. What's something you recommend to almost everyone you meet? Then ask Has anyone taken you up on it?
16. What's a tradition from where you grew up that you still keep? Then ask How do you celebrate it now?
17. What's the best trip you've taken on a tiny budget? Then ask What made it work?
18. What's something you're weirdly good at? Then ask How did you find out?
19. What did you do last weekend that you'd happily do again? Then ask Who were you with?
20. What's the first thing you notice when you arrive in a new city? Then ask What would a visitor notice first about this one?
21. What's a smell that takes you straight back to being a kid? Then ask Where does it take you?
22. What's a dish you can make without a recipe? Then ask Who did you learn it from?
23. What's the last thing you looked up just because you were curious? Then ask Where did that lead?
24. What's a game you're unbeatable at? Then ask Want to prove it?
25. How do you like to start a good morning? Then ask And what happens on a bad one?
26. What's a phrase people say you use all the time? Then ask Where did you pick it up?
27. What were you obsessed with as a teenager? Then ask Is any of it still around?
28. What's the best live show you've ever been to? Then ask What made that night?
29. What's something in your home with a good story behind it? Then ask Who's in the story?
30. Where would you take a visitor first in your city? Then ask What would you want them to notice?
31. When you were a kid, what did you think adults did all day? Then ask So what do you actually do all day?
32. What's a party trick you'd show us if we asked nicely? Then ask Can we ask nicely?
33. What's the most competitive you've ever gotten over something small? Then ask Did you win?
34. What's a first impression you got completely wrong? Then ask What changed your mind?
35. What's the last thing you did for the first time? Then ask How did it go?
36. What's the strangest food combination you've tried and actually liked? Then ask Would you make it for us?
37. If you could have dinner with any character from a book or movie, who would it be? Then ask What would you ask them first?
38. What's the assumption people make about you that's furthest from the truth? Then ask Where do you think it comes from?
39. What's a place a stranger showed you that no guidebook would have? Then ask How did you two meet?
40. What's the hardest travel moment that's now your favorite story? Then ask How long before it got funny?
41. What's a place you found by accident that you'd never have found on purpose? Then ask Have you been back?
42. If you had to spend a year in a city you've never visited, where would you hope to land? Then ask What would you miss from home?
43. If you could watch any moment in history as it happened, which would you pick? Then ask Where would you want to stand?
44. What's something you've built with your own hands? Then ask Is it still standing?
45. What are you looking forward to in the next few months? Then ask Who are you doing it with?
46. What's a local custom you picked up on a trip and never dropped? Then ask Has anyone at home caught on?
47. You get one carry-on and 24 hours' notice. Where are you going? Then ask What goes in the bag first?
48. If someone here planned your next vacation with zero input from you, who would you trust with it? Then ask Where do you think they'd send you?
49. If your next trip had to be to the hometown of someone here, whose would you pick? Then ask What should they show you first?
50. What's one subject schools should teach but don't? Then ask Who would you want teaching it?
51. Where do you want to live when you retire, and what will you do all day? Then ask Why wait?
52. What would your younger self be amazed you do now? Then ask Would they have believed it?
53. What do you find easy that other people find hard? Then ask And the other way around?
54. What's a moment from this year you'd put in a time capsule? Then ask Why that one?
55. Who's someone you admire who isn't famous? Then ask Have you told them?
56. What's the best thing about the age you are now? Then ask What are you looking forward to about the next one?
57. What's something a younger person has taught you? Then ask Did they know they were teaching it?
58. What song sums up where you are in life right now? Then ask Can you play us a bit?
59. What do you collect, even if you didn't mean to? Then ask What's the story behind the first one?
60. Where do you do your best thinking? Then ask What's the last idea you had there?

Deep questions to ask your friends

61. Who in your life has changed your mind about something big? Then ask What did they say?
62. What's a decision that changed the direction of your life? Then ask Did it feel big at the time?
63. Who believed in you before you believed in yourself? Then ask Do they know?
64. What are you proud of that most people don't know about? Then ask Why keep it quiet?
65. What's a piece of advice you ignored and later wished you hadn't? Then ask Who gave it to you?
66. Which part of your week would you happily do for free? Then ask How much time do you get for it?
67. Which year of your life would you relive for a week? Then ask What would you make sure to do again?
68. What's a place that made you who you are? Then ask When were you last there?
69. What do you hope people say about you after you leave a room? Then ask Do you think they do?
70. What's something you're working toward this year? Then ask What's the next step?
71. What's the best advice anyone has given you about work? Then ask Do you still follow it?
72. Who taught you something you still use every week? Then ask What was it like learning from them?
73. What's something you've gotten better at with age? Then ask What helped the most?
74. What's something you believed five years ago that you don't anymore? Then ask What changed it?
75. When do you feel most like yourself? Then ask How often do you get that?
76. What's a compliment you still remember? Then ask Why did it stick?
77. What do you wish more people asked you about? Then ask Can I ask now?
78. What's a risk you're glad you took? Then ask Would you take it again?
79. What does a good friend do that most people don't? Then ask Who does that for you?
80. What's something you're still figuring out about yourself? Then ask What's helped so far?
81. What's a version of your life you sometimes imagine? Then ask What's in it that isn't in this one?
82. When did you last feel proud of someone else? Then ask Did you tell them?
83. What do you need more of in your life right now? Then ask What's in the way?
84. What's a fear you've gotten over? Then ask How did you do it?
85. Who do you call first when something good happens? Then ask Is it the same person when things go wrong?
86. What's a small kindness from a stranger you still think about? Then ask Have you passed it on?
87. What does home mean to you now? Then ask Has it always meant that?
88. What's something you used to be embarrassed about that you now like about yourself? Then ask When did that flip?
89. Which friendship has taught you the most? Then ask What did it teach you?
90. What would you tell your 18-year-old self, if they'd listen? Then ask What would they tell you back?
91. What does success look like to you, apart from money and titles? Then ask How close are you?
92. What part of your work makes you feel useful? Then ask When did you last feel that?
93. What's a value you got from your family that you still live by? Then ask Is there one you've let go of?
94. What do you need from people when you're having a hard week? Then ask Do they usually know?
95. When did you last feel completely at peace? Then ask What were you doing?
96. What does a good apology look like to you? Then ask Who's the best at it that you know?
97. What do you think you'll care less about in 10 years? Then ask And more about?
98. Who do you miss that you could still reach out to? Then ask What would you say first?
99. What's the bravest thing you've done that nobody saw? Then ask Why did you do it?
100. What's a promise you've kept to yourself? Then ask How hard was it?
101. How do you know when you need a break? Then ask What do you usually do about it?
102. When do you feel most connected to other people? Then ask What usually comes before it?
103. What's something you'd like to be braver about? Then ask What would brave look like?
104. What's a memory you go back to when you need cheering up? Then ask When did you last go back to it?
105. What's something you hope never changes about you? Then ask Who would notice first if it did?
106. What's a tradition you'd like to start? Then ask Who would you start it with?
107. What do you want more of from your friendships? Then ask What would you give more of?
108. In what ways are you like the people who raised you? Then ask Which ones are you glad about?
109. What does rest look like for you? Then ask Do you get enough of it?
110. What's a mistake that turned out to be the best thing that happened to you? Then ask When did you realize?
111. If you could talk to your future self, what would you ask? Then ask What do you hope they'd say?
112. What's a change you've noticed in yourself lately, big or small? Then ask Who noticed it first?
113. What's a place that only meant something because getting there was hard? Then ask Would you go back the easy way?
114. When did saying yes to a stranger's idea beat anything you had planned? Then ask Do you say yes more now?
115. What's the nicest thing you've done for a friend? Then ask And the nicest thing a friend has done for you?
116. What's a place that made you feel small, in the best way? Then ask What were you thinking about there?
117. What's something travel made you do that you were sure you couldn't? Then ask Could you do it at home now?
118. What do you spend most of your time thinking about these days? Then ask Or who?
119. What title would you give this chapter of your life? Then ask And the last one?
120. What's the hardest decision you've ever had to make? Then ask How did you decide?
121. Where have you felt furthest from your ordinary life? Then ask What did you bring back with you?
122. What's a recent decision you're proud of? Then ask What made it hard?
123. Which three words would your closest friends use to describe you? Then ask Which one would you argue with?
124. What small habit has changed your life the most? Then ask How did it start?

Juicy questions to ask your friends

A little daring, never explicit

125. What's a hill you'd happily die on, even though it doesn't matter at all? Then ask Who argues with you about it most?
126. What's the most spontaneous thing you've ever done? Then ask Would you do it again?
127. What's a rule you broke as a kid that you're still a bit proud of? Then ask Did anyone find out?
128. What's something you pretend to enjoy for other people's sake? Then ask Who would be most surprised?
129. What's a strong opinion you have about how people should behave at dinner? Then ask Have you ever broken it yourself?
130. What's the most trouble you've ever gotten into for something that wasn't your fault? Then ask Did you ever clear your name?
131. What's the most dramatic exit you've ever made? Then ask Would you do it the same way?
132. If you could drop one obligation tomorrow with no fallout, what would it be? Then ask What would you do with the time?
133. What have you done this year that surprised everyone who knows you? Then ask Did it surprise you too?
134. What's a story your family still tells about you that you'd rather they didn't? Then ask How much of it is true?
135. What's a habit your coworkers would never guess you have? Then ask Are you going to tell them?
136. What's something you want to do that scares you a little? Then ask When are you doing it?
137. What's the most memorable pickup line you've used or heard? Then ask Did it work?
138. What's something you did on a trip that you'd never do at home, and don't regret? Then ask Who was with you?
139. If all your exes were in one room, what's the one thing they'd have in common? Then ask Is it you?
140. When did you know you were wrong and keep going anyway, out of pure stubbornness? Then ask Who finally made you stop?
141. What's a rule you live by that other people find strange? Then ask Where did it come from?
142. What's an argument you lost that you're still a little sore about? Then ask Were they right?
143. What's the most honest feedback you've ever been given? Then ask Did it change anything?
144. What harmless rule would you break tomorrow if nobody would ever find out? Then ask Why that one?
145. What's something you've never said out loud but might tonight? Then ask Why tonight?
146. What's a truth about yourself you only admitted recently? Then ask Who did you tell first?
147. What's a part of yourself you keep hidden at work? Then ask What would happen if you didn't?
148. When were you last jealous, and what was it about? Then ask What did it tell you?
149. What's a question you're scared someone will ask you? Then ask Want to answer it anyway?
150. What's the most rebellious thing you've done as an adult? Then ask Who was most surprised?
151. When were you last a bad friend? Then ask What would you do differently now?