This post may contain affiliate links, meaning if you book or buy something through one of these links, I may earn an affiliate commission at no additional cost to you. Learn more
Prepare for tears of joy, aching cheeks, and some real rofl moments with these funny questions, perfect for silly, casual conversation with your friends, family, or partner.
Funny Questions to Ask
To Ask Friends
1. What’s the most embarrassing haircut you’ve ever had?
2. What’s the most useless invention of all time?
3. If you were in a competition to do the worst karaoke rendition of all time, what song would you choose to sing?
4. What’s the least sexy name?
5. What’s your opinion on pineapple on pizza?
6. What’s the funniest joke you’ve ever heard?
7. What movie makes you laugh every time without fail?
8. Which former president most resembles a potato?
9. What’s the funniest WiFi name you’ve ever seen?
10. Have you ever created your own joke? If so, what is it?
11. How often do you tell a white lie?
12. Have you ever secretly taken money from your parents?
13. Which accent do you think is the most annoying?
14. What’s your least favorite baby name?
15. Have you ever been on holiday and disliked the place you visited?
16. Do you make any strange noises in your sleep?
17. What’s the most awkward interaction you’ve ever had?
18. What’s your go-to fast food order?
19. If you could only ever eat one pizza topping again, which topping would you choose?
20. What’s the weirdest meal you’ve ever eaten?
21. If a clone of you with the same personality was created, do you think you’d get along with them?
22. Have you ever met somebody who looked exactly like you?
23. If the world was filled with people with your personality, do you think it would be a better or a worse place?
24. If you sat next to your favorite celebrity on a plane or train, what would you ask them?
25. Have you ever accidentally broken something and lied about how it happened?
26. If you could create a chocolate bar from scratch, what would it have in it?
To Ask a Guy
27. What’s the best prank you’ve ever played on somebody?
28. What’s your go-to chat up line?
29. What’s your favorite cheesy lyric?
30. Have you ever laughed so hard that you spat out your drink?
31. Which romantic comedy movie do you secretly cry at every time?
32. How long would you survive in a zombie apocalypse, and how do you think you’d die?
33. Have you ever gone a whole day commando?
34. Where’s the most embarrassing place you’ve ever farted?
34. If you were offered $1000 to eat five pizzas by yourself in one meal, could you do it?
35. Who was your first crush when you were growing up?
36. What’s the strangest thing that’s ever happened to you on a first date?
37. If you could choose to have one superpower, what superpower would you choose, and what would you do with it?
38. If you could appoint anybody you wanted (apart from yourself) as the president, who would you choose?
39. If you could have dinner with five people from history, who would you have dinner with?
40. Have you ever done something nice just so that you could brag about it afterward?
50. Which celebrity would you most like to be friends with?
52. What’s your favorite meme, and why do you love it?
53. What weird food combination do you secretly love?
54. What would be more embarrassing if it was released to the world – your teenage diary or your internet history?
55. Have you ever peed in a pool?
To Ask a Girl
56. Who’s your weird celebrity crush?
57. What’s your most embarrassing moment ever?
58. What’s the worst makeup tip you’ve ever tried?
59. Have you ever stolen anything?
60. What’s the most random reason you’ve ever said no to somebody who asked you on a date?
61. What’s the most embarrassing fashion trend you’ve ever tried?
62. If you were offered $1000 to eat ten pancakes in five minutes, could you do it?
63. What’s the cringiest chat-up line a guy has ever used on you?
64. Which famous character from TV or movies does your best friend remind you of?
65. If you were a dessert, what dessert do you think you’d be?
66. What last-minute revelation about a partner would make you leave them at the altar?
67. What’s the strangest gift you’ve ever been given?
68. What’s the strangest gift you’ve ever given somebody else?
69. Which fruit do you think most matches your personality?
70. If you ever appeared on the news, what do you think it would be for?
71. What’s the strangest thing you’ve ever ordered online?
72. If you become the president for just one day, what law would you immediately bring in?
73. What’s your favorite ice cream topping?
74. What’s your most irrational fear?
75. What five food products do you pick up from the grocery store almost every time?
To Ask Coworkers
76. Who in the workplace would be most likely to have a side job as a clown?
77. What’s the strangest thing you have in your home?
78. What part of your job is the most boring?
79. Have you ever done anything embarrassing during a job interview?
80. If you could pretend your ancestors invented something, what invention would you choose?
81. Which celebrity do you think most resembles you?
82. What thing did you believe as a kid that you now realize is completely untrue?
83. Have you ever fallen asleep in a place you shouldn’t have, like at the movies or during class?
84. Which musical instrument do you think sounds the most annoying?
85. What did you most frequently get into trouble for at school?
86. Have you ever fallen for an April Fool’s Day prank?
87. If you had to fight a tiger or a shark, which one would you choose?
88. Would you rather have to swim in gravy or in custard?
89. How would you describe the internet in one word?
90. What was your first-ever email address?
91. Which dance move do you show off at every party?
92. When you were a child, did you ever pretend to be unwell so you could have a day off school?
93. What’s the most spontaneous thing you’ve ever done?
94. What word would you add to the dictionary, and what would its definition be?
95. If animals could talk, which animal would tell the best jokes?
96. What school subject do you wish you never had to study again?
97. Which mythical creature would you most want to exist in real life?
98. If you had the power of invisibility just for one day, what would you do with it?
99. If you could wake up tomorrow in the body of an animal, what animal would you choose?
100. If an apple and an orange had a fight, who would win?
101. Do you think we eat or drink soup?
102. If you were a crayon, what color crayon would you be?
103. If you could swap places with a dog or a cat, which would you choose to be?
104. If all the foods went to school, which food would be the most popular?
105. Would you rather have blue skin or pink hair?
106. What’s a nickname that your friends call you? If you don’t have a nickname, what nickname would you choose for yourself?
107. What do you think hamsters think about?
108. How many of your friends do you think you’d need to help you lift up an elephant?
109. Who’s your favorite cartoon character from TV or movies?
110. If every time you spoke, instead of speaking like a human, you made the sound an animal makes (such as a woof or moo), which animal sound would you want to make?
111. What thing do your parents do that embarrasses you the most?
112. What’s your most useless talent?
113. What vegetable would you pay $1000 to never have to eat again?
114. If an alien landed on planet Earth, what would you say to them?
115. Do you have the toilet paper over or under?
116. Is there any food that chocolate would taste disgusting with?
116. What thing that’s typically considered a guilty pleasure do you love?
117. Which animal do you think would be best at changing a lightbulb?
118. If you could have secretly listened in on any conversation in history, which conversation would you choose?
119. What’s the funniest book you’ve ever read?
110. Which guy’s name do you think sounds the most like a dog?
111. Has anybody ever accidentally walked in on you naked?
112. What do you think is your most annoying habit?
113. Have you ever laughed so hard it made your tummy hurt?
114. What’s the funniest line from a movie or TV show you’ve ever heard?
115. Could you eat ice cream using your feet for $1000?
116. What would you be most likely to be arrested for?
117. If aliens exist, what do you think they look like?
118. What reality TV show do you secretly love?
119. What’s the biggest lie you’ve ever told?
120. Would you rather never eat sugar again or never eat pizza again?
121. What rumor about you is actually true?
122. Have you ever cheated on an exam?
123. What are your three most used emojis, and what do they say about you?
124. Who’s your favorite comedian?
125. Did you ever pretend you were going to run away from home when you were a child?
126. Would you rather be a member of a royal family for a week or have magical powers for a day?
127. If you could have any animal (even a wild one!) as a pet, which animal would you choose?
128. What dating profile bio would turn you off?
129. Have you ever made up an excuse to avoid doing something?
130. Who is the most random person that’s ever appeared in your dreams?
131. What’s the latest time you’ve ever slept until?
131. Which farts are the most embarrassing, silent and smelly, or loud with no scent?
132. What food do you know is unhealthy but can’t help eating anyway?
133. What’s the most embarrassing injury you’ve ever had?
Having a proper laugh with someone is one of the healthiest things you can do for your friendship or relationship with them.
Have some of these questions in the back of your mind on hand so that when you want to be a little more fun and casual, you can take the conversation to some truly hilarious places.
You Might Also Like to Read
- 200+ Best Questions to Ask Friends for Memorable Conversations
- 100+ Best What If Questions for Fascinating Conversations
- 200+ Questions for Couples: Best Questions to Ask Your Partner
Keep these funny questions for safekeeping by saving this article to one of your conversation starter Pinterest boards.