Conversation Starters

How to play

1. Draw a question and give the first person a minute. Answers can be a word or a story.
2. For big groups and video calls, pick Quick questions and go around fast; for small groups, try Medium or Deeper.
3. Anyone can pass. A good icebreaker never puts someone on the spot.

All 105 questions

1. What's a project you've worked on that you're quietly proud of
2. What's one thing you learned recently that surprised you
3. What's a book, podcast, or video that changed how you work
4. Who's someone outside your field whose work you admire
5. What's the best team you've ever been on, and what made it work
6. What's the most useful thing you learned at your first job
7. Which fictional character would make the best coworker, and why
8. What's a podcast or channel you'd recommend to this group
9. What's the most interesting fact you know about your field
10. What's something you know a lot about that has nothing to do with your job
11. If you started a side business tomorrow, what would it be
12. What's a part of your job that people outside it don't quite understand
13. What's the best "I didn't know I needed this" tool or gadget you own
14. What's the most memorable presentation you've ever seen
15. What's the most creative fix you've seen for a boring problem
16. What's the strangest thing you've ever seen on a walk
17. What's a movie you could quote from start to finish
18. What's the silliest rule you've ever had to follow
19. What's the most overrated food
20. Which fictional world would you least want to live in
21. What's something you believed for way too long before finding out it wasn't true
22. What's a trend you'd bring back, and one you're glad is gone
23. What's the most unexpected thing that has ever made you cry laughing
24. What's a silly hill you will happily die on (like whether a hot dog is a sandwich)
25. What's the funniest misunderstanding you've been part of
26. What's a story your friends always ask you to tell
27. What's something you're secretly very competitive about
28. What's your go-to karaoke song, even if you'd never actually sing it
29. What's the best movie you've seen this year
30. What's the last show you couldn't stop watching
31. What's a word you just love saying
32. What's a place you'd love to see someday
33. What did you want to be when you were little
34. What's the best concert, play, or live show you've ever been to
35. What's a place that feels like home to you
36. What's a book you've recommended to people more than once
37. What's a tradition you've kept up for years
38. What's the most interesting thing about where you grew up
39. What's the best road trip, train ride, or long walk you've ever taken
40. What's a movie you think everyone should see
41. What's the most beautiful place you've ever been, even if it's close to home
42. Who's someone who taught you something you still use every day
43. What's your ideal day, from start to finish
44. What's a song that takes you right back to a specific time in your life
45. What's the best meal you've ever had
46. What's a smell, taste, or sound that reminds you of being a kid
47. What's a topic you could talk about for an hour with no prep
48. What are three things on your bucket list
49. What's a question you love being asked
50. What's something you've learned from a friend
51. What's a random fact you love telling people
52. What's the most adventurous thing you've ever done
53. What's the kindest thing a stranger has ever done for you
54. Tell us about a moment you felt really proud of yourself
55. If you could have dinner with any three people, living or historical, who would they be
56. What's the best thing you've ever found by accident
57. What's a decision that turned out better than you expected
58. What's a place you've lived in or visited that surprised you
59. What's the most interesting conversation you've had with a stranger
60. What's a book you read in school that stuck with you
61. What's a problem, big or small, you'd love to see solved in your lifetime
62. What's a piece of technology you can't imagine living without
63. What's something old-fashioned you still love
64. What's a skill you think everyone should learn
65. What's an everyday thing you think is wildly underrated
66. What do you think people 100 years from now will find funny about how we live today
67. If you could ask your future self one question, what would it be
68. If you could watch any moment in history happen, which would you pick
69. If you could become an expert in anything overnight, what would you choose
70. What's a rule you try to live by
71. What's something you've changed your mind about in the last few years
72. What's something you're curious about right now
73. What's a movie or book ending you'd rewrite, and how
74. What's the best story behind something you own
75. What's a hobby you think more people would love if they tried it
76. What's a place you'd take a visitor to show off your town
77. What advice would you give your younger self
78. What's a tiny moment from this year you want to remember
79. What invention do you wish existed
80. What's a question you've always wanted to know the answer to
81. What's something you do that makes an ordinary day feel special
82. Which fictional character do you relate to most
83. If you had a free weekend and all the supplies you needed, what would you make
84. What's the most memorable meal you've ever cooked, or tried to
85. Where do you get your best ideas
86. What's an ordinary skill you think is secretly impressive
87. What's a museum, park, or landmark you love
88. What would you do with an extra hour every day
89. What's a skill you had as a kid that you've completely lost
90. What's the best "small world" coincidence that's ever happened to you
91. What's one thing you wish you'd been taught in school
92. What's something you used to find hard that now feels easy
93. Who's your favorite character from a book
94. What would you put in a time capsule for kids 50 years from now
95. What's the best dream you can remember
96. If you could make one new rule that everyone had to follow, what would it be
97. What's the most interesting bug or animal you've seen up close
98. What's one question you'd ask an astronaut
99. What's a job you'd invent if it didn't exist yet
100. What's the best holiday movie, special, or song
101. What's the best thing about the end of the year
102. What's a hope you have for the new year
103. What's the most memorable holiday meal you've ever had
104. What's a holiday or celebration from another culture you'd love to experience
105. What's a holiday memory that still makes you laugh

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