70+ Funny Icebreaker Questions (Free PDF)

They say everyone is a comedian, not because they tell jokes, but because life is funny and everyone’s lived through it. These icebreaker questions will make any conversation entertaining and enjoyable.

Written by Ed Moss on July 2, 2020

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They say laughter is the best medicine, and we totally stand by it. A good dose of humor gets everyone engaging, every time. Any environment where laughter is present will help lower the tensions, nervousness, and intimidation of being in a room with group of strangers for the first time.

Jokes are great, but they often only work for punch lines and or as quick wits—save them for parties. Instead, asking funny icebreaker questions can actually be a better way to get someone to reveal something hilarious about their past experiences.

Asking about funny moments or even personal opinions on funny topics, like “what Netflix show do you dislike the most?” are great ways to keep your conversations entertaining. Most people tend to appreciate these moments of joy and let happiness sink in. It’s easier to connect when everyone’s happy and having a good time.

Put on your funny hat, whatever that is—for us, it’s a hat that looks like this.

And start with these icebreaker questions, carefully crafted for your personal humor. However, we did keep it PG, this is a family site after all.

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Download a pdf of these questions you can use in meetings, classrooms or other in-person events.
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  1. Are you wearing pants during this meeting?
  2. How often do you work from your bed?
  3. Choose two famous people from history you’d want on your team during a zombie apocalypse.
  4. Describe Your Worst Date Ever.
  5. Do you have a guilty pleasure?
  6. Do you know any good jokes? Or corny dad jokes?
  7. Have you ever gotten super lost? What happened?
  8. Have you ever lied about an interest or talent to impress someone?
  9. Hit the Treadmill or Hit the Couch?
  10. How would you rate your laugh out of 10?
  11. If you could be on a reality TV show, which one would you choose and why?
  12. If you could commit any crime and get away with it what would you choose and why?
  13. If you could eliminate one food so that no one would eat it ever again, what would you pick to destroy?
  14. If you could have any celebrity be your best friend, which celebrity would you pick?
  15. If you had to be an animal, which animal would you be?
  16. If you had to delete all but 3 apps from your smartphone, which ones would you keep?
  17. If you had to use a fake name, what fake name would you make up?
  18. If you were a candy bar, which candy bar would you be?
  19. If you were a vegetable, what vegetable would you be?
  20. If you were a wrestler what would be your entrance theme song?
  21. If you were left on a deserted island with either your worst enemy or no one, which would you choose? Why?
  22. Is a hot dog a sandwich?
  23. Steve Urkel or Kimmy Gibler?
  24. What’s the worst piece of advice you’ve ever been given?
  25. What are your top 3 most hated foods?
  26. What band would you be embarrassed to admit you listen to?
  27. What blog or website are you embarrassed to admit you love?
  28. What breed of dog would you be?
  29. What childish things do you still do as an adult?
  30. What completely safe animal are you inexplicably afraid of?
  31. What did you get into the most trouble for with your parents as a kid?
  32. What Disney/cartoon character were you inexplicably afraid of as a kid?
  33. What do you pretend to hate but actually love?
  34. What fashion trend needs to end now?
  35. What food can you not stand?
  36. What food will you never eat?
  37. What fruit or vegetable would you most want to be?
  38. What is one article of clothing that someone could wear that would make you walk out on a date with them?
  39. What is the most obscure superpower you would want?
  40. What is the strangest food you have eaten?
  41. What is the weirdest thing you've ever seen in your workspace?
  42. What is the weirdest thing you’ve ever eaten for breakfast that is not a breakfast food?
  43. What part of elementary school do you wish you could incorporate into your adult life? (i.e. naptime)
  44. What physical thing (hurricanes, bugs, heights) scares you the most?
  45. What was the most embarrassing thing you have done on a date?
  46. What was the worst job you ever had?
  47. What was the worst style choice you ever made?
  48. What was the worst style or fashion trend you ever embraced?
  49. What was the worst travel experience of your life?
  50. What was your childhood nickname?
  51. What were words you couldn’t pronounce as a child, so you made up your own?
  52. What would you do if you were invisible for 24 hours?
  53. What’s a funny (appropriate) pick-up line that works for you?
  54. What’s a nickname people actually call you?
  55. What’s the best prank you’ve ever played on someone?
  56. What’s the craziest fashion trend you ever rocked?
  57. What’s the grossest food you ever had to eat to be polite?
  58. What’s the most ridiculous thing your parents ever did to embarrass you?
  59. What’s the strangest family tradition in your family?
  60. What’s the strangest food you ever tried?
  61. What’s the weirdest food you’ve ever eaten?
  62. What’s the worst haircut you ever had?
  63. What’s the worst job you’ve ever had?
  64. What’s the worst misspelling of your name you’ve ever seen?
  65. What’s the worst thing you ever did as a kid — and got away with?
  66. What’s your best idea for a reality TV show?
  67. What’s your funniest talent? Or un-talent?
  68. What’s your go-to karaoke anthem?
  69. What’s your most embarrassing moment from your teen years?
  70. What’s your real favorite book, and what book do you pretend is your favorite to sound smart?
  71. Where is the strangest place you’ve ever fallen asleep?
  72. Which celebrity do you shamelessly follow in the news?
  73. Which movie made you laugh the most?
  74. Who is your least favorite actor?

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