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210 Funny Questions to Ask a Guy And Get to Know Him Better
Most of the time, humor is the best way to make a conversation more fun. These “funny questions to ask a guy” are perfect to help you with that. Check them out!
Humor lightens everything! With a good sense of humor, you can have more fun when socializing and learn things people wouldn’t share if the conversation weren’t funny. Hence, for your next meet-up with your guy friend, brother, or romantic partner, we recommend using “funny questions to ask a guy” to make the conversation flow more smoothly.
Now, to do this, it is important to remember that guys are different from girls, and hence, find different things relatable. Of course, you can’t ask them about their “first period” and it may not be very satisfying to ask how long it takes them to get ready in the morning. However, you might ask them who they think the most powerful superhero is and see their face brighten up almost instantly (note that this is highly relative).
You can ask them anecdotal questions about their crushes, favorite childhood memories, embarrassing moments, favorite vacations, favorite food, and dates, as well as hypothetical scenarios about what they’d wear for the rest of their lives, if they want to time travel, etc. You can customize these questions based on the personality of the guy you’re thinking about.
Is he a morning person or a night owl? Does he have any bizarre talent or theory? Does he believe in the concept of soul mates? Does he like pineapple on pizza? What’s his biggest fear? These are some things you can consider if you wish to personalize these questions for him. Try to ask questions that either make you two crack up or lead to deeper conversations, but don’t cause awkward silences!
Trust us, the following fun questions that we’ve curated, would help you have a hearty time with this guy, which would be full of warmth and giggles. So, without further ado, scroll away to give them a read.
210 Funniest Questions to Ask a Guy
1. What’s the first thing you’d do if you woke up as a girl?
2. What’s the most embarrassing thing you’ve ever done in front of a crush?
3. What’s your favorite dad joke?
4. What’s your most embarrassing guilty pleasure?
5. Would you rather wear Crocs or Big Red Boots for the rest of your life?
6. What’s the funniest thing that has ever happened to you in public?
7. Would you rather be bald or have no eyebrows?
8. Have you ever done anything embarrassing on purpose?
9. What’s the best prank you’ve ever pulled?
10. Show me the funniest picture you have saved on your phone.
11. What’s the most embarrassing thing that has happened to you on a date?
12. If you were a meme, which one would you be?
13. What was your favorite insult as a child?
14. Would you rather eat only chocolate every day for the rest of your life or only potato chips?
15. What is the silliest fear you have that you know is completely irrational?
16. What’s the funniest thing in the world to you?
17. What’s your most useless skill?
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18. Have you ever gone to a corner store and stolen a candy bar?
19. What’s an embarrassing song or band that you secretly love?
20. Do you believe that socks have feelings and deserve to be paired up?
21. What’s your go-to dance move when no one’s watching?
22. Is a hot dog a sandwich?
23. If you could create a new slang term for something common, what would it be?
24. What gives you the ick?
25. Do you believe in Bigfoot, the Loch Ness monster, or other mythical creatures?
26. What’s the funniest thing you believed in as a child?
27. Have you ever been caught talking to yourself in public?
28. If you could fight any historical figure, who would it be?
29. What’s the worst text you’ve sent to the wrong person?
30. What’s the weirdest thing you’ve seen in someone’s house?
31. What would your superhero name and superpower be in the world of slapstick comedy?
32. What’s the most absurd way you’ve tried to impress someone you liked?
33. Have you ever had a funny but embarrassing encounter with a celebrity?
34. What’s your go-to karaoke song when you want to make people laugh?
35. If your pet had a catchphrase, what would it be?
36. Have you ever laughed at a joke you didn’t understand just to fit in?
37. What’s your go-to karaoke song when you want to make people laugh?
Interesting And Deep Questions to Ask Men
38. If you could fight any historical figure, who would it be?
39. If you could have any superpower, but it could only be used for mundane tasks, what would it be and why?
40. What inanimate object would you delete from existence?
41. When did the phrase, “looks can be deceiving” actually happen to you?
42. What celebrity would be the worst leader of our country?
43. What would you do if I pretended to trip and injure myself right here?
44. What movie trope irritates you the most?
45. If you were given $1,000,000 tomorrow, what would you do with it?
46. If you were a superhero with a sidekick, what quirky ability would your sidekick have?
47. What’s the most ridiculous food combination you’ve ever concocted and enjoyed?
48. What was your favorite family activity when you were little?
49. How long do you think you would last in a zombie apocalypse?
50. If you could have any comedian narrate your life story, who would it be?
51. Did you ever have a horrifying experience ordering fast food?
52. What’s the most unnecessary white lie you’ve ever told someone?
53. What scene from a movie scarred you for life?
54. What’s the most absurd thing you’ve seen someone do for a dare?
55. If you could create a new holiday based on your favorite hobby, what would it be called?
56. If you were stranded on a deserted island, which three things would you want to have with you?
57. If your life had a sitcom title, what would it be?
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58. What’s your most unique talent that you think could break a world record?
59. If you could have any historical figure as your imaginary drinking buddy, who would it be?
60. What board game can you not play civilly?
61. If your life were a board game, what would be the penalties for landing on certain spaces?
62. If animals could talk, which one would have the best sense of humor?
63. What’s your funniest superstition or irrational fear?
64. If you had the chance to live on Mars but could never come back, would you do it?
65. What’s the most ridiculous way you’ve injured yourself?
66. What’s one fact you wish you could unlearn?
67. If you could have a conversation with your future self, what hilarious advice would they give you?
68. If you could swap lives with any cartoon character for a day, who would it be and what mischief would you get up to?
69. What movie quote do you use the most?
70. What’s the most bizarre item on your bucket list?
71. What’s something interesting you learned this week?
72. If you could have a conversation with any famous painting, which one would it be and what would you talk about?
73. If you had a theme song that played every time you entered a room, what would it be?
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Funny And Witty Questions to Ask a Guy
74. If you could only ever be one, would you rather be smart or happy? Why?
75. If you can still remember, what are your funniest childhood memories?
76. How do you hang toilet paper: over or under?
77. What has been the strangest thing a visitor has done at your home?
78. If you had a talking parrot, what embarrassing secret would it accidentally reveal?
79. What’s the most embarrassing thing you’ve ever googled?
80. Are you afraid of staying home alone?
81. If you were a snack, what would your tagline be on the packaging?
82. What’s the funniest Wi-Fi name you’ve ever come across?
83. What does the word “ok” mean for you?
84. If you could be a professional at any random skill, what would it be?
85. Who do you think actually tests the specific dog food when they say that it has a new and improved flavor?
86. Have you ever gone a day without wearing underwear?
87. If you could choose to be any animated character, who would it be?
88. What’s the strangest dream you’ve ever had that still makes you laugh?
89. If you could invent a holiday, what would it celebrate, and how would you celebrate it?
90. Have you ever forgotten to bring your wallet when you’ve been scheduled to pay for a meal?
91. What’s the most bizarre thing you’ve caught yourself daydreaming about?
92. What’s the weirdest thing you’ve caught yourself doing when you thought no one was looking?
93. What musical instrument has the most annoying sound to you?
94. Would you rather always shout or always whisper?
95. If you were a stand-up philosopher, what profound yet funny life advice would you give?
96. Do you believe it is possible to inflate a balloon when underwater?
97. If you could invent a holiday, what would it celebrate, and how would you celebrate it?
98. What’s your most creative use of emojis to convey a message?
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Cute And Silly Questions to Ask a Guy
99. Would you rather talk like Yoda or breathe like Darth Vader?
100. What’s the silliest thing that made you laugh uncontrollably?
101. If your life had a theme song composed entirely of animal sounds, what would it sound like?
102. Would you rather always feel like you have to sneeze or sneeze 500 times a day?
103. Do you think pineapple belongs on pizza?
104. Would you rather talk like Donald Duck when you’re angry or turn into the Hulk when you’re turned on?
105. Do you still sleep with a stuffed toy?
106. If you could create a new holiday tradition, what would it involve?
107. What’s the cringiest thing you’ve done to get someone’s attention?
108. If you had to choose between always speaking in puns or rhymes, which would it be?
109. Do mermaids have live babies or lay eggs?
110. Have you ever accidentally called someone by the wrong name during a date or during an intimate moment?
111. Do you believe in aliens, or are they just trying to avoid meeting us?
112. What’s the most ridiculous costume you’ve ever worn to a party?
113. What’s your most embarrassing autocorrect fail?
114. Describe your personal fragrance in three funny words.
115. What’s the grossest thing you did as a kid?
116. If the last thing you ate is the only thing you can eat for the rest of your life, how soon will you die?
117. Where does prune juice come from if prunes are dried plums?
118. How do you sleep, with your eyes open or closed?
119. If you were a potato, how would you like to be cooked?
120. What’s the silliest reason you’ve ever burst into laughter in a serious situation?
121. If you could create a new slang word, what would it mean, and how would you use it?
122. Do you think the sea is salty because the shore never waves back at it?
123. What’s the weirdest item you’ve ever bought on impulse?
124. What’s the most ridiculous fashion trend you’ve ever tried?
125. What’s the funniest name you can think of for a new color?
126. Describe your dream job in the form of a limerick.
Fun And Flirty Questions to Ask Guy
127. What’s a funny reason why you’d get arrested?
128. What kind of people did you have a crush on as a kid?
129. Which person do you know that totally reminds you of a character in a TV show or movie?
130. What’s your weirdest turn-on?
131. What’s your favorite scent?
132. If I was a guy, do you think we’d be friends?
133. What song gets you in the mood?
134. When did you have your first kiss?
135. Who was your first celebrity crush?
136. What’s your favorite way to unwind?
137. What keeps you up at night?
138. If coffee wasn’t legal, what would it be called on the black market?
139. What’s your favorite season?
140. What’s your biggest pet peeve on a date?
141. Have you ever sent a dirty text to the wrong person?
142. Do you prefer being single or being in a relationship?
143. Out of 10, how would you rate yourself as a kisser?
144. What’s your dream vacation?
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145. Which nursery rhyme makes you think of me?
146. Are you a night owl or an early bird?
147. What’s your favorite meal of the day? And why?
148. Do you prefer going out or staying in?
149. Have you ever been in a secret relationship?
150. Do you believe in love at first sight?
151. What’s your biggest guilty pleasure?
152. Would you rather be too hot or too cold?
153. Are you more introverted or extroverted?
154. What’s the best concert you’ve attended?
155. Have you ever gone skinny dipping?
156. What is the wildest fantasy you’ve ever had?
157. What’s my most attractive body part?
158. What’s the most surprising thing about you?
159. What’s your unpopular opinion or hot take?
160. Would you rather live without salt or sugar?
161. What’s the best pick-up line you’ve ever used?
Funny Questions to Ask Your Boyfriend
162. What’s a bizarre talent of yours that I don’t know about?
163. Between Superman and Goku, who do you think would win?
164. What’s your favorite thing about me?
165. If you could put one condiment inside your belly button, what would it be and why?
166. Have you ever come into contact with human remains?
167. How much of a handyman are you?
168. What’s the first thing you told your friends about me?
169. What's the first thing you wash in the shower?
170. If you could describe me in one word, what would it be?
171. When was the last time you screwed anything up and no one noticed?
172. What was your first impression of me?
173. What has been the funniest or strangest thing that has happened to you on a first date?
174. If you were me for a day, what would you do?
175. Do you know how to fold a fitted sheet?
176. What’s the weirdest dream you’ve ever had involving a celebrity?
177. What’s your favorite memory of the two of us?
178. If we hosted a comedy roast, what would you say about me?
179. What is the worst possible name you might give your child?
180. Have you accidentally glued your hands together when doing a craft project?
181. What’s the most absurd way you’ve tried to overcome a fear?
182. Which aspects of mine do you admire and which do you despise?
183. What’s the most ridiculous item you’ve considered bringing to a desert island?
184. If you were given the death penalty, what would your last meal be?
185. What do you think the first person to milk a cow was actually trying to do?
186. Can you tell me one memory that you’ve never shared with me?
187. If you had to replace your hands with objects already in your house, what would you pick?
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188. Who do you wish you could torture for the rest of your life?
189. If we had a Netflix show, what would it be called?
190. Have you ever been called out at school for wearing something embarrassing?
191. If your life had a warning label, what would it say?
192. In terms of appearance, which athlete do you believe most closely resembles you?
193. In terms of appearance, which actor do you believe most closely resembles you?
194. If we were to have a boxing match, who do you think would win?
195. Have you ever offered to help anyone else with their homework in return for something specific?
196. When was the last time you felt butterflies?
197. Do you prefer kissing or cuddling?
198. If you could have an unlimited supply of one thing for the rest of your life, what would you choose?
199. How would you feel leading a parade dedicated to the most mundane thing you did today?
200. If every time you snapped your fingers, a random item of clothing would change color, what’s the first thing you’d snap at?
201. Do you like dancing when no one is looking?
202. What song title best describes your last trip to the bathroom?
203. Why do we refer to an alarm clock as going "off" when it actually turns on?
204. If you could have any fictional character as your wingman/wingwoman on a night out, who would it be?
205. If you had to choose one fruit, what would you like to be?
206. If you were a kitchen appliance, based on your personality, which one would you be?
207. Have your parents ever found you trying to leave the house without permission?
208. What’s the most awkward thing that’s happened to you while shopping?
209. Do you think penguins have knees? If yes, what do you think they look like when they’re weak in their knees?
210. What can I do right now that would turn you on?
You don’t have to use the above-mentioned “funny questions to ask a guy” as they are. You’re more than welcome to tweak and personalize them based on what you think would elicit the best response from this guy that you’re thinking about. In fact, we encourage that! To help you further, we’ve categorized the questions a bit based on what kind of funny they are, and whether they can be used romantically or platonically.
When it comes to romantic questions to ask your boyfriend or a guy you’ve just started seeing, it helps a great deal to make the questions a bit more personal and spicy. If this guy is a friend, your brother, or some other relative, don’t shy away from getting a bit silly with the questions and let your hypothetical imagination go wild when asking them. Hope these questions help you have a great time. Happy laughing!
