175 Funny Questions to Ask to Start a Winning Conversation

Humour is also a terrific way to break the ice when first getting to know someone.

To help you get better acquainted with others around you, I’ve put together this long list of funny questions to ask in conversations.

Keep reading below for funny random questions to ask your friends, colleagues, and/or significant other!

Looking for funny questions of the day? You might also like these:

Funny Questions to Get to Know Someone

Headed out on a first date? Want to get to know a new neighbour or work colleague? Try out some of these silly questions to break the ice.

1. What’s a song you pretend you don’t like because it’s embarrassing that you love it?

2. If you could travel anywhere in the world, where would you go?

3. What is the most ludicrous thing you’ve ever bought?

4. What’s your ideal way to spend a lazy Sunday?

5. Do you have any hidden talents or unusual hobbies?

6. How long do you think you’d survive in a zombie apocalypse?

7. What kid’s movie did you think was too scary when you were a child?

8. Have you ever eaten something that made you immediately regret it?

9. What age would you choose if you could spend a week at any other age?

10. What is something that you just recently realized that you are embarrassed you didn’t realize earlier?

11. What are the unwritten rules of where you work?

12. What are the craziest adventures you want to try in your life?

13. What’s the best type of cheese?

14. What is something that is really popular now, but in five years everyone will look back on and be embarrassed by?

15. What’s the most interesting thing about you that most people don’t know?

16. If you got to choose your name, what would it be and why?

17. What’s your dream job, and why?

18. What fictional character is amazing in their book/show/movie, but would be insufferable if you had to deal with them in mundane everyday situations?

19. What’s the most ridiculous thing your family has ever argued about?

20. Which animal do you believe would be the meanest if they could talk?

21. If you had the right to award the worst movie in history, which movie would you give it to?

22. What is your spirit animal?

23. If you were arrested with no explanation, what would your friends and family assume you had done?

24. What’s the most adventurous thing you’ve ever done?

25. Have you ever sent a text message to the wrong person by mistake?

26. Do you know how to fold a fitted sheet?

27. What’s the craziest thing you’ve ever heard someone say in a meeting?

28. If you could remove one colour from the whole world, what would it be and why?

29. What would be the outcome if the government decided to make everything illegal?

30. What’s the best inside joke you’ve been a part of?

31. What movie completely changes its plot when you change one letter in its title? What’s the new movie about?

32. If peanut butter wasn’t called peanut butter, what would it be called?

33. Why do we say people work like dogs if they work all day, while dogs do nothing but lie around?

Silly Questions to Ask Your Girlfriend/Boyfriend

How much do you know about your significant other? Open up an exciting discussion (and learn something new) with some of these funny questions.

34. What is the sexiest and least sexy name?

35. Do you think there may be true love at first sight?

36. What is your most embarrassing moment from high school?

37. If you could date any cartoon character, who would you be and why?

38. Which body part do you wish you could detach and why?

39. What’s invisible but you wish people could see?

40. When was the last time you screwed anything up and no one noticed?

41. If someone asked to be your apprentice and learn all that you know, what would you teach them?

42. What’s the best piece of advice you’d give to someone starting a relationship?

43. What’s the funniest family vacation you’ve ever been on?

44. What secret conspiracy would you like to actually start letting other people know?

45. What would be the absolute worst name you could give your child?

46. Do you have any sinful desires?

47. What do you think is the worst thing that a person can put on their bio on a dating app?

48. What is something you refuse to share?

49. If you could describe me in three words, what would they be?

50. What are some things that are okay to occasionally do but definitely not okay to do every day?

51. What’s the first thing you wash in the shower?

52. What are three items you could buy together at the grocery store to make the cashier laugh?

53. What is the most embarrassing thing you have ever worn?

54. If you had to choose between having a permanent unibrow or having no eyebrows at all, which one would you choose?

55. In terms of appearance, which celebrity do you believe most closely resembles you?

56. Which famous person would you like to be your wingman, if you could?

57. Who was your first celebrity crush, and are you still crushing on them?

58. If your family were a sports team, which sport would you play?

59. What is the worst possible name you might give your child?

60. If you were held at gunpoint and told that if you didn’t impress them with your dance moves you would be killed, what dance moves would you bust out?

61. Did your ex have any quirky habits that used to drive you crazy?

62. What used to be considered trashy but now is very classy?

63. What would your favourite dance move be if you were at a wedding?

64. Have you ever gone a day without wearing underwear?

65. What’s the most humiliating item in your bedroom right now?

66. If you were a mad scientist, what scientific experiment would you run if money and ethics weren’t an issue?

Funny Questions to Ask Friends

Board games are great, but they’re not the only path to a laughter-filled evening. Why not liven up your next get-together with some funny random questions to ask your friends?

67. Is cereal soup? Why or why not?

68. What movie would be greatly improved if it was made into a musical?

69. If all the States in the USA were represented by food, what food would each state be represented by?

70. What was the most cringe-worthy date you ever went on?

71. What are some fun ways to answer everyday questions like “How’s it going” or “What do you do?”

72. If you could switch careers tomorrow, what would you do instead?

73. What is the most humiliating incident that has ever happened to you on a date?

74. Have you ever tried to lick your own toes?

75. What was the most embarrassing moment in your entire childhood?

76. If you had to choose one animal to help you win a fight, which animal would you choose?

77. What are some of the nicknames you have for customers or coworkers?

78. Which insect would you pick to eat if you had to?

79. Where was the most inappropriate or embarrassing place you’ve farted?

80. What’s the weirdest thing a guest has done at your house?

81. If you were transported 300 years into the past with no clothes or anything else, how would you prove that you were from the future?

82. What’s the most ridiculous thing you’ve ever bought on a shopping spree?

83. What are some fun and interesting alternatives to war that countries could settle their differences with?

84. What has been the most surprising incident that has ever happened to you?

85. What sport would you choose to play if you could only play one for the rest of your life?

86. If your family were a TV show, what genre would it be?

87. What’s the craziest thing you’ve ever done with your ex?

88. What’s the most ridiculous fact you know?

89. What’s the reason for saying ‘after dark’ when it’s actually really after light?

90. What’s the weirdest smell you have ever smelled?

91. What’s the most unexpected thing that’s ever happened at work?

92. Who actually tests the specific dog food when they say that it has a new and improved flavour?

93. If your family had to live on a deserted island, who would be the most useful?

94. How many chickens would it take to kill an elephant?

95. What is your favourite dance move to do when you are at the club?

96. What’s the craziest thing you’ve ever done after getting really drunk?

97. What is something that everyone looks stupid doing?

Funny Random Questions to Spark Conversation

No matter how long you’ve known someone, there’s always something interesting to learn about the way they think. Ask your closest friends or family members these random questions and get ready to be amazed by their replies!

98. What secret conspiracy would you like to start?

99. If your five-year-old self suddenly found themselves inhabiting your current body, what would your five-year-old self do first?

100. What is the silliest thing you have ever said in public?

101. Do mermaids have live babies or lay eggs?

102. How would you describe your dream weekend?

103. What is the funniest corporate/business screw-up you have heard of?

104. If you were wrongfully put into an insane asylum, how would you convince them that you’re actually sane and not just pretending to be sane?

105. Do you think aliens really exist?

106. What colour would you like if you had to eat a crayon straight from the box?

107. What mythical creature would improve the world most if it existed?

108. What inanimate object do you wish you could eliminate from existence?

109. In 40 years, what will people be nostalgic for?

110. What would some fairy tales be like if they took place in the present and included modern technology and culture?

111. What would you do if you won a million dollars?

112. What would be the creepiest thing you could say while passing a stranger on the street?

113. Who in your family is the biggest drama queen?

114. What would you watch on Netflix if you could only watch one show for the rest of your life?

115. What would be the best-worst name for different types of businesses? (dry cleaners, amusement parks, etc.)

116. What was the sweetest thing someone has ever done for you?

117. What would be the worst “buy one get one free” sale of all time?

118. In one sentence, how would you sum up the internet?

119. What sport would be the funniest to add a mandatory amount of alcohol to?

120. If you could morph two animals to make one super animal, what two animals would you choose? Why?

121. What was the most daring thing you ever did?

122. What is it that you keep wanting to smell despite the fact that it doesn’t smell particularly good?

123. What was the weirdest thing you’ve ever done to get the attention of someone?

124. If you could have any superpower, what would it be?

125. What’s your favourite childhood memory?

126. Have you ever been in a secret relationship?

127. If you were stranded on a desert island and could only bring three things, what would they be?

128. Who would you like to live with if you could trade lives with any literary figure, and why?

129. How do you feel about putting pineapple on pizza?

130. What is the funniest name you have actually heard used in the real world?

Bonus: Even More Funny Get to Know You Questions

Can’t get enough funny questions to get to know someone? Keep the conversation going with these funny questions to ask!

131. Which celebrity, if any, would you choose to have as your mentor?

132. Have you ever had an imaginary friend?

133. Where would you like to time travel: back to the past or into the future?

134. What would be the coolest animal to scale up to the size of a horse?

135. What’s the best Wi-Fi name you’ve ever seen?

136. What ridiculous and untrue, yet slightly plausible, theories can you come up with for the cause of common ailments like headaches or cavities?

137. What would the world be like if it was filled with male and female copies of you?

138. Which animal do you think would be the most polite?

139. What part of a kid’s movie completely scarred you?

140. If life were a video game, what would some of the cheat codes be?

141. What would be the worst thing for the government to make illegal?

142. If you could replace all of the grass in the world with something else, what would it be?

143. Which of your parents’ actions has caused you the most embarrassment?

144. Why do round pizzas come in square boxes?

145. What has been the funniest or strangest thing that has happened to you on a first date?

146. What kind of secret society would you like to start?

147. What two totally normal things become really weird if you do them back to back?

148. If you had to describe your personality using a kitchen appliance, what would it be?

149. Who would you invite to supper, whether they were alive or dead?

150. Which musical instrument has the most annoying sound to you?

151. Do you sometimes hear certain voices in your head, too?

152. Is a hotdog a sandwich? Why or why not?

153. What set of items could you buy that would make the cashier the most uncomfortable?

154. Who do you know that really reminds you of a character in a TV show or movie?

155. What is the weirdest thing you have seen in someone else’s home?

156. If you were to be banned from your local library, what would be the reason?

157. What’s one thing your dogs could say that would completely ruin your image if they could talk?

158. In all honesty, what are some of your guilty pleasures that you are willing to admit?

159. If you had the power to shrink any one object and carry it with you in your pocket, which item would it be?

160. Would you rather be forced to wear shoes every second of your life or never be able to wear shoes again?

161. If you could use magic to do one mundane task for the rest of your life, what would it be? What would you name the spell?

162. If you were king/queen for a day, what would be your first rule that you would change?

163. Who would you appoint as the president of the Internet, and why?

164. What’s the strangest purchase you’ve made or almost made on Amazon?

165. If we were to have a boxing match, who do you think would win?

166. What is the best excuse for being late you’ve heard or used?

167. What’s the weirdest thing you’ve given someone as a gift?

168. What do you think the first person to milk a cow was actually trying to do?

169. If you could create a holiday, what would it be called and how would we celebrate it?

170. Why wasn’t the word “gullible” listed in the dictionary?

171. If you had a pet parrot, what would you teach it to say?

172. What is one band or musician you would love to party with?

173. What is the most useless skill you possess?

174. What is the worst fashion decision you’ve ever made? Do you have a picture of it?

175. In the event of the apocalypse, what three places are you going to first to gather supplies?

Your List of Funny Questions of the Day

There’s no doubt about it — humour is one of the best ways to break the ice!

Whether you’re getting to know new colleagues at work or hanging out with your best friends, these funny random questions are sure to spark great conversation.

So what are you waiting for? Pour another cup of coffee (or your favourite cocktail) and get ready to laugh aloud as you discuss these funny questions.

Now that you know hundreds of funny questions to ask people, what’s next? Keep the conversation rolling by discussing this list of strange and exotic foods to try while travelling.