200+ Funny Questions to Ask a Guy to Make Him Laugh

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As the saying goes, laughter is the best medicine. It’s no surprise that humor plays an important role in building relationships and fostering social interactions. A good sense of humor can make you more attractive and approachable, break the ice on a first date, and keep things interesting in an established relationship.

If you’re looking to inject some fun and lightheartedness into your conversations with the guys in your life, you’ve come to the right place. In this article, we’ll be sharing over 50 funny questions to ask a guy that are sure to get you both laughing and bonding.

Whether you’re on a first date, hanging out with friends, or just looking to add some humor to your daily interactions, these questions are the perfect way to break the ice and get to know each other better. From silly hypotheticals to playful inquiries about his preferences and experiences, there’s something here for everyone.

So sit back, relax, and get ready to have some fun with our list of funny questions to ask a guy!

Related: 101 Funny Questions to Ask Your Girlfriend and Make Her Laugh Out Loud

200+ Funny Questions to Ask a Guy

Here are some funny questions you can ask a guy to lighten up the conversation:

1. Do you believe in aliens?
2. If you could only eat one food for the rest of your life, what would it be?
3. What’s the worst fashion trend you’ve ever participated in?
4. Do you have any strange habits or rituals?
5. Have you ever accidentally worn mismatched shoes or socks?
6. Would you rather have a pet unicorn or a pet dragon?
7. What’s the silliest thing you’ve ever done for love?
8. Have you ever danced in public and embarrassed yourself?
9. If you could trade places with any fictional character, who would it be?
10. What’s the funniest joke you know by heart?
11. Do you have any hidden talents?
12. If you were a superhero, what would your superpower be?
13. What’s the weirdest dream you’ve ever had?
14. Do you prefer cake or pie?
15. Have you ever gotten lost in your own city?
16. If you could have any animal as a pet, what would it be?
17. What’s the craziest thing you’ve ever done for a dare?
18. Would you rather be a giant hamster or a tiny elephant?
19. What’s the weirdest thing you’ve ever eaten?
20. Do you have any phobias or fears?
21. If you could live in any time period, which would you choose?
22. Do you have a celebrity crush?
23. What’s the worst pickup line you’ve ever used?
24. Have you ever accidentally sent a text to the wrong person?
25. Would you rather fight 100 duck-sized horses or one horse-sized duck?
26. What’s the most embarrassing thing that’s ever happened to you?
27. If you could only listen to one song for the rest of your life, what would it be?
28. What’s the craziest thing you’ve ever eaten for breakfast?
29. Do you believe in ghosts or the supernatural?
30. If you could be any character from a TV show or movie, who would it be?
31. Do you have any weird talents or skills?
32. Would you rather have a third arm or a third leg?
33. Have you ever laughed so hard you peed your pants?
34. If you could time travel to any historical event, which one would it be?
35. What’s the most ridiculous thing you’ve ever bought online?
36. If you could be any animal, which one would you choose?
37. What’s the most embarrassing thing in your room right now?
38. If you could only watch one TV show for the rest of your life, what would it be?
39. Have you ever accidentally walked into the wrong restroom?
40. If you could have any job for a day, what would it be?
41. What’s the weirdest thing you’ve ever searched for on the internet?
42. Would you rather be able to fly or be invisible?
43. Have you ever fallen asleep in a public place?
44. If you could have any superpower, what would it be?
45. What’s the most ridiculous thing you’ve ever done in the name of love?
46. Do you have any strange allergies?
47. If you could switch lives with anyone for a day, who would it be?
48. Have you ever accidentally worn something backwards or inside-out?
49. What’s the most useless talent you have?
50. If you could only eat one color of food for the rest of your life, what would it be?
51. Do you have any irrational fears?
52. If you could have any job in the world, what would it be?
53. Have you ever been to a psychic or fortune teller?
54. If you could have any fictional vehicle (e.g. the Batmobile) what would it be?
55. Have you ever been on a blind date? How did it go?
56. If you could have any celebrity be your personal assistant, who would it be?
57. Do you believe in karma or fate?
58. Have you ever tried to cook something and completely messed it up?
59. If you could only watch one movie for the rest of your life, what would it be?
60. Have you ever pranked someone or been pranked?
61. If you could choose any language to learn fluently, which would it be?
62. Do you believe in soulmates or love at first sight?
63. Have you ever been to a psychic or fortune teller?
64. If you could be any character from a book, who would it be?
65. Do you have any embarrassing nicknames?
66. If you could travel anywhere in the world right now, where would you go?
67. Have you ever been in a fight? What happened?
68. If you could choose any animal to be your spirit animal, which would it be?
69. What’s the most interesting thing you’ve ever learned?
70. Have you ever broken a bone?
71. If you could switch lives with anyone for a week, who would it be?
72. Do you believe in ghosts or the supernatural?
73. What’s your favorite type of cuisine?
74. If you could have any superpower for a day, what would it be?
75. Have you ever been skydiving or bungee jumping?
76. What’s the most spontaneous thing you’ve ever done?
77. If you could only eat one type of food for the rest of your life, what would it be?
78. Do you have any secret talents or hobbies?
79. If you could be any character from a TV show, who would it be?
80. Have you ever been to a music festival? Which one?
81. If you could be any historical figure, who would it be?
82. Do you prefer the beach or the mountains?
83. Have you ever won a contest or competition?
84. If you could have any job in the world for a day, what would it be?
85. What’s the most unusual thing you’ve ever eaten?
86. Have you ever been in a car accident?
87. If you could only wear one outfit for the rest of your life, what would it be?
88. What’s your favorite type of weather?
89. Do you have any phobias or fears?
90. If you could be any character from a video game, who would it be?
91. Have you ever been to a live sports event? Which one?
92. If you could have any vehicle, what would it be?
93. Do you believe in luck or chance?
94. If you could choose any time period to live in, which would it be?
95. Have you ever traveled outside of the country? Where did you go?
96. If you could only listen to one genre of music for the rest of your life, what would it be?
97. What’s the most interesting place you’ve ever visited?
98. If you could have any job in the entertainment industry, what would it be?
99. Have you ever met a celebrity? Who was it?
100. If you could have any job in the science field, what would it be?
101. What’s your favorite type of dessert?
102. Do you believe in any conspiracy theories?
103. Have you ever eaten a whole pizza by yourself?
104. If you could switch lives with any cartoon character, who would it be?
105. What’s the craziest dream you’ve ever had?
106. If you could only wear one color for the rest of your life, what would it be?
107. Have you ever accidentally sent a text to the wrong person that was embarrassing?
108. If you could have any animal as a pet, except for a dog or a cat, what would it be?
109. Have you ever accidentally called someone by the wrong name?
110. If you could choose any superpower to have, but it had to be completely useless, what would it be?
111. What’s the most embarrassing thing you’ve ever worn in public?
112. If you could only use one emoji for the rest of your life, which one would it be?
113. Have you ever tried to do something and failed spectacularly?
114. If you were a superhero, what would your theme song be?
115. Have you ever tried a food combination that was weird but surprisingly good?
116. If you were stranded on a deserted island, what three things would you want with you?
117. Have you ever had a wardrobe malfunction in public?
118. If you could only communicate through one social media platform for the rest of your life, which one would it be?
119. If you could have any fictional creature as a pet, what would it be?
120. Have you ever walked into a glass door or window?
121. If you could only watch one TV show for the rest of your life, but it had to be a kids show, which one would it be?
122. Have you ever accidentally eaten something that wasn’t meant for you?
123. If you could have any celebrity as your best friend, who would it be?
124. Have you ever tried to do something that looked easy, but turned out to be incredibly difficult?
125. If you could only eat one type of candy for the rest of your life, what would it be?
126. Have you ever had a crush on a cartoon character?
127. If you could switch lives with any historical figure for a day, who would it be?
128. Have you ever had a dream where you were naked in public?
129. If you could only eat one fruit for the rest of your life, what would it be?
130. Have you ever had a bad haircut that you regretted?
131. If you could have any job for a day, but it had to be a job that no one wants to do, what would it be?
132. Have you ever accidentally sent a message to your crush that was meant for someone else?
133. If you could be any character from The Simpsons, who would it be?
134. Have you ever gotten lost in your own hometown?
135. If you could only wear one type of shoe for the rest of your life, what would it be?
136. Have you ever eaten so much that you felt sick?
137. If you could only have one type of cheese for the rest of your life, what would it be?
138. Have you ever fallen asleep in a public place and woken up with strangers staring at you?
139. If you could only watch one movie for the rest of your life, but it had to be a bad movie, which one would it be?
140. Have you ever tried to do a DIY project and failed miserably?
141. If you could have any actor play you in a movie about your life, who would it be?
142. Have you ever been caught talking to yourself?
143. Have you ever had a wardrobe malfunction on a first date?
144. If you could have any celebrity as your personal chef, who would it be?
145. Have you ever had a dream where you were famous?
146. If you could only eat one type of sandwich for the rest of your life, what would it be?
147. Have you ever accidentally worn your shirt inside out all day?
148. If you could have any animal’s tail, which one would it be?
149. Have you ever gotten lost in a mall or department store?
150. If you could only have one type of pizza topping for the rest of your life, what would it be?
151. Have you ever laughed so hard that you snorted?
152. If you could be any character from Friends, who would it be?
153. Have you ever worn a Halloween costume that no one understood?
154. If you could only listen to one band or artist for the rest of your life, who would it be?
155. Have you ever fallen asleep during a movie and missed the ending?
156. If you could be any character from The Office, who would it be?
157. Have you ever been so hungry that you ate something you didn’t like?
158. If you could have any movie or TV character as your roommate, who would it be?
159. Have you ever tried a beauty or grooming treatment that went wrong?
160. If you could have any fictional object from a book or movie, what would it be?
161. Have you ever accidentally used the wrong pronoun when referring to someone?
162. If you could have any character from Game of Thrones as your best friend, who would it be?
163. Have you ever accidentally sent a text message to the wrong person and it was embarrassing?
164. If you could only have one type of candy bar for the rest of your life, what would it be?
165. Have you ever tripped or fallen in a public place?
166. If you could be any character from The Big Bang Theory, who would it be?
167. Have you ever had a date where everything went wrong?
168. If you could only wear one color for the rest of your life, what would it be?
169. Have you ever eaten something that smelled bad but tasted good?
170. If you could have any movie or TV character as your significant other, who would it be?
171. Have you ever accidentally hit “reply all” on an email that you shouldn’t have?
172. If you could have any character from Seinfeld as your best friend, who would it be?
173. Have you ever accidentally walked into the wrong room or bathroom?
174. If you could only have one type of dessert for the rest of your life, what would it be?
175. Have you ever laughed so hard that you cried?
176. If you could be any character from How I Met Your Mother, who would it be?
177. Have you ever been so scared that you ran away from something harmless?
178. If you could only have one type of potato dish for the rest of your life, what would it be?
179. Have you ever accidentally sent a text message to your boss that was meant for your friend?
180. If you could have any character from Parks and Recreation as your best friend, who would it be?
181. Have you ever eaten so much that you had to unbutton your pants?
182. If you could only have one type of fruit for the rest of your life, what would it be?
183. Have you ever been mistaken for someone else?
184. Have you ever accidentally worn two different shoes?
185. If you could have any cartoon character as your wingman, who would it be?
186. Have you ever had a date where you accidentally spilled something on yourself?
187. If you could have any fictional weapon, what would it be?
188. Have you ever gotten into a fight with a vending machine?
189. If you could have any character from The Walking Dead as your best friend, who would it be?
190. Have you ever accidentally walked into the wrong class or meeting?
191. If you could only have one type of snack for the rest of your life, what would it be?
192. Have you ever had a dream where you were an animal?
193. If you could have any character from The Marvel Cinematic Universe as your best friend, who would it be?
194. Have you ever gotten lost while driving and ended up in a completely different state?
195. If you could have any fictional vehicle, what would it be?
196. Have you ever accidentally used the wrong bathroom?
197. If you could have any character from The Lord of the Rings as your best friend, who would it be?
198. Have you ever had a date where you accidentally wore the wrong clothes?
199. If you could only have one type of condiment for the rest of your life, what would it be?
200. Have you ever had a dream where you were a superhero?
201. If you could have any character from Breaking Bad as your best friend, who would it be?
202. Have you ever accidentally walked into a glass door?
203. If you could only have one type of breakfast food for the rest of your life, what would it be?
204. Have you ever had a dream where you were famous but for something embarrassing?
205. If you could have any character from The Matrix as your best friend, who would it be?
206. Have you ever gotten lost in a corn maze?
207. If you could have any fictional animal as a pet, what would it be?
208. Have you ever accidentally worn your shirt inside out on a date?
209. If you could only have one type of noodle for the rest of your life, what would it be?
210. Have you ever had a dream where you were a villain?
211. If you could have any character from The Fast and the Furious as your best friend, who would it be?
212. Have you ever gotten lost in a forest?
213. If you could only have one type of beverage for the rest of your life, what would it be?
214. Have you ever had a dream where you were a character from a video game?
215. If you could have any character from The Hunger Games as your best friend, who would it be?
216. Have you ever gotten lost in a city you’ve never been to before?
217. If you could have any fictional technology, what would it be?
218. Have you ever had a dream where you were a character from a TV show?
219. If you could have any character from Harry Potter as your best friend, who would it be?
220. Have you ever accidentally left the price tag on an item of clothing you were wearing?
221. If you could only have one type of seafood for the rest of your life, what would it be?
222. Have you ever had a dream where you were a famous athlete?
223. If you could have any character from The Office (US) as your best friend, who would it be?
224. Have you ever gotten lost in a mall parking lot?

Getting to Know Him

Questions about his preferences and habits

When it comes to getting to know a guy, his preferences and habits can reveal a lot about his personality and interests. Here are some questions to ask that are sure to spark some interesting conversations:

1. What’s your go-to comfort food?

We all have those foods that make us feel warm and cozy inside. Whether it’s a classic dish from your childhood or a guilty pleasure snack, asking him about his favorite comfort food can give you a glimpse into his tastes and upbringing.

2. Do you prefer cats or dogs?

The age-old debate between cat lovers and dog lovers is one that never gets old. Asking him about his preference can lead to some playful banter and give you an idea of whether you two would be a good match if you’re a proud pet owner.

3. Are you a morning person or a night owl?

Some people love waking up with the sunrise, while others thrive when the moon is high in the sky. Finding out his sleep habits can help you plan future dates and activities that cater to his natural rhythm.

4. What’s your favorite type of music?

Music is a universal language that can bring people together, and learning about his musical tastes can help you bond over shared interests or introduce each other to new genres and artists.

5. If you could only watch one movie for the rest of your life, what would it be?

This question is a fun way to learn about his movie preferences and get a glimpse into his personality. Does he prefer action-packed blockbusters or heartfelt indie films? The answer might surprise you.

Questions about his experiences and memories

Asking about his past experiences and memories can reveal a lot about his sense of humor and the types of adventures he’s had in his life. Here are some questions to get the ball rolling:

1. What’s the funniest thing that’s ever happened to you?

Everyone has a hilarious story or embarrassing moment that they love to share. Ask him about the funniest thing that’s ever happened to him and get ready for a good laugh.

2. Have you ever been in a food fight?

Food fights are a childhood classic, but have you ever participated in one as an adult? This question can lead to some fun memories and stories about his mischievous side.

3. What’s the craziest thing you’ve ever done?

Whether it’s skydiving, bungee jumping, or something else entirely, we’ve all done something a little crazy in our lives. Asking him about his wildest adventure can lead to some exciting stories and shared interests.

4. Have you ever been in a prank war?

Prank wars can be a fun way to bond with friends and family, but they can also get pretty intense. Find out if he’s ever been in a prank war and get ready for some hilarious tales of revenge and shenanigans.

5. What’s the worst haircut you’ve ever had?

We’ve all had a bad haircut at some point in our lives, and asking him about his worst haircut can lead to some humorous memories and self-deprecating humor.

Let’s Get Silly

Questions that will get him laughing

Laughter is the best medicine, and these questions are sure to get him chuckling and lightening the mood. Here are some silly and playful questions to ask:

1. If you were a vegetable, which one would you be?

This question is a playful way to get to know his personality and interests. Is he more of a cucumber or a carrot?

2. Have you ever tried to lick your elbow?

This silly question is a classic and is sure to get him laughing as he tries to contort his arm to lick his elbow.

3. What’s the most useless talent you have?

We all have talents, but some are more useful than others. This question can lead to some playful self-deprecation and shared laughs.

4. If you could be any fictional character, who would you be?

Whether he’s a superhero fan or a lover of classic literature, this question can lead to some playful hypothetical scenarios and reveal his interests and aspirations.

5. What’s the weirdest thing you’ve ever eaten?

From exotic cuisine to bizarre culinary creations, there are plenty of strange foods out there to try. Find out about his adventurous side and maybe even get some ideas for your next culinary adventure.

Questions that will make him think

Sometimes it’s fun to pose hypothetical scenarios and make him think about interesting and imaginative situations. Here are some questions to get his creativity flowing:

1. If animals could talk, which one do you think would be the most annoying?

This question is a fun way to imagine a world where animals can talk and lead to some playful banter about the personalities of different animals.

2. If you could have any superpower but it had to be silly, what would it be?

From the ability to turn invisible but only for five seconds at a time to the power to control squirrels, this question can lead to some hilarious and imaginative answers.

3. If you were a ghost, where would you haunt?

This question is a playful way to think about the afterlife and can lead to some interesting insights into his personality and sense of humor.

4. If you could switch lives with someone for a day, who would it be?

From celebrities to historical figures, there are plenty of people to choose from when it comes to switching lives for a day. This question can lead to some fun hypothetical scenarios and reveal his interests and aspirations.

5. If you could have any job for a day, what would it be?

This question is a fun way to think about different career paths and can lead to some playful banter and imaginative scenarios. Plus, it can reveal his interests and aspirations beyond the typical small talk.

Conclusion

Recap of the importance of humor in relationships and social interactions

Humor is an essential ingredient in any successful relationship or social interaction. Whether it’s a first date, a long-term relationship, or a casual hangout with friends, being able to laugh and make others laugh can bring people closer together and create lasting memories. By asking funny questions, you can not only break the ice and lighten the mood but also show off your playful and engaging personality.

Final thoughts and encouragement to use these questions to have some fun and laughter with the guys in your life.

So there you have it, a comprehensive list of funny questions to ask a guy! We hope that these questions have sparked your creativity and given you some new ideas for livening up your social interactions. Whether you’re looking to get to know a new guy, strengthen an existing relationship, or just have some fun with your friends, these questions are sure to inspire some laughter and lively conversation.

Remember, the key to successful social interactions is to be yourself and have fun. So don’t be afraid to let your personality shine through and use these questions as a starting point for your own unique conversations. With a little humor and creativity, you’re sure to have some unforgettable moments and build lasting relationships.

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