Take your conversation to the next level by asking him one of these 300 funny questions to make him laugh.
Below you’ll find some fun questions that are flirty, dirty, romantic, weird, random, awkward, and even inappropriate. Whether you ask him in person or over text, these will certainly get the conversation going and even make him laugh.
- Funny Questions To Ask A Guy To Make Him Laugh
- Dirty Questions To Ask A Guy To Make Him Laugh
- Romantic Questions To Ask Your Boyfriend To Make Him Laugh
- Weird Funny Questions To Ask Guys
- Random Funny Questions To Ask A Guy
- Funny Questions To Ask A Guy Over Text
- Funny Date Questions To Ask A Guy
- Awkward Funny Questions To Ask A Guy
- Funny Inappropriate Questions To Ask A Guy
- Dumb Funny Questions To Ask A Guy
- Flirty Funny Questions To Ask A Guy
- Funny Deal Breaker Questions To Ask A Guy
Funny Questions To Ask A Guy To Make Him Laugh
1. Can you think of a food that would make you choose death before eating it?
2. When was the last time you pushed a pull door?
3. What is the oldest thing in your refrigerator?
4. Have you ever purchased something that has caused the cashier to give you a strange look?
5. Who do you know that peaked in high school?
6. Ever been caught in the middle of doing something embarrassing by someone?
7. As an “expectations vs. reality” meme, what two pictures depict your life?
8. Which would you choose if you had to choose between losing all your teeth or all your hair?
9. How would you name your parents if they were renamed according to their personalities?
10. What is one thing your pet could say that would completely ruin your reputation if they could talk?
11. If you could be extremely beautiful with a slightly below-average IQ or aggressively ugly with a higher IQ than 99% of the population, which would you prefer?
12. What is the best thing about being a guy?
13. If you were forced to replace your hand with something else, what would you choose, and why?
14. Do you have a favorite weird smell?
15. What did you do today besides chatting with me?
16. In the unlikely event you were arrested, what would you be accused of?
17. What’s the best response to Wassup?
18. What is the most hilarious childhood experience you can recall?
19. Whose conversations would you like to hear if you could be invisible?
20. What dance style would you use if you were entering a dance contest?
21. What is your personal theme song?
22. Is there something you find funny that no one else does?
23. What is the one bodily function you would want to eliminate if you had the choice?
24. Have you ever set something on fire while you were cooking?
25. If you could slap one celebrity, who would it be and why?
26. What bucket list activity would you like to do with me?
27. What secret club would you start if you could?
28. Which joke would you tell if you had to use only emojis?
29. In the event of a zombie apocalypse, what would you do first?
30. What animal would you choose if you could only speak through animal noises?
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Dirty Questions To Ask A Guy To Make Him Laugh
31. Which part of your body do you consider the sexiest?
32. Have you ever tried skinny dipping?
33. Have you ever slept naked?
34. If you could share a bed with anyone, who would it be?
35. Is there one thing that turns you on the most?
36. Do you prefer a girl to be naughty or nice?
37. What is your biggest fantasy?
38. Are you a good kisser?
39. What would your name be if you were a stripper?
40. What would you never do in your bedroom again?
41. Are you more likely to respond to dirty talk, or are you more likely to respond to actions?
42. How do you feel about public displays of affection?
43. What do you wear to bed?
44. Do you know how to play strip poker?
45. What is the weirdest thing you’ve dreamed about doing with a girl?
46. Who would you choose if you could sleep with any celebrity?
47. Is it hot in here, or is it just you?
48. How do you feel about friends with benefits?
49. Do you have any experience playing dirty truth or dare?
50. Can you recall a sexy scene from a movie you’ll never forget?
Romantic Questions To Ask Your Boyfriend To Make Him Laugh
51. Is there a type of girl who sweeps you off your feet?
52. Do you know how much I smile when I think of you?
53. Is there a relationship between you and my heart that causes it to race whenever I see you?
54. Why are you so charming?
55. Do you usually listen to your heart or your brain?
56. What’s your love language?
57. Does love at first sight really exist?
58. Do you still remember the day we met for the first time?
59. Do you have a song in mind when you think of me?
60. When did you first realize you loved me?
61. When you were in college, how many girls were crushing on you?
62. If I were completely different, would you still love me?
63. Do you think we’re soulmates?
64. Would you dance with me even if it’s just the two of us on the dance floor?
65. As a future partner, do you think we’ll do better?
66. What is the most romantic gesture you have ever made?
67. How cute do I look to you?
68. Have you ever had the ‘Princess Leia and the gold biking’ fantasy?
69. Do you think of me when you’re alone?
70. Are you a romantic?
71. Is there a way to tell when you’ve fallen in love with someone?
72. Which would you prefer: falling in love and losing or never loving at all?
73. Would you rather have a picnic under the stars or have dinner at a romantic restaurant?
74. Do you go the extra mile to make someone happy?
75. What would it be like to spend an entire day with me?
76. Have you ever been surprised by someone’s romantic gesture?
77. When do you let your guard down in a relationship?
78. Are you influenced by your friends’ opinions regarding your relationships?
79. What makes you fall in love with someone?
80. Do you remember the last time you felt butterflies?
Weird Funny Questions To Ask Guys
81. Do you ever talk to your dog?
82. Do you sometimes hear certain voices in your head, too?
83. Have you ever been caught cheating on a test?
84. What do you think of pineapple on pizza?
85. Have you ever been caught dancing in front of a mirror?
86. Do you know how long it takes to boil water in a microwave?
87. Are there any activities you enjoy that you’re actually too old for?
88. Have you ever called an unknown number to prank them?
89. Is there something you used to believe but is no longer true?
90. Can you fold a fitted sheet?
91. Have you ever fallen asleep during class?
92. If you could make one absolute rule for a day that everyone should follow, what would it be?
93. If you were to be banned from your local library, what would be the reason?
94. What color would you remove from the world if you could?
95. If animals could talk, which would be the rudest?
96. Which conspiracy theory would you break if you could?
97. What is the best Wi-Fi name you have seen?
98. Have you ever stolen a candy bar from a corner store?
99. Are you interested in becoming famous? In what kind of way?
100. Do you like girls wearing boyfriend jeans?
Random Funny Questions To Ask A Guy
101. Can you tell me which celebrity you most resemble?
102. Do you find horror movies scary?
103. Have you ever been caught singing out loud when you didn’t expect anyone to hear you?
104. Do you have a favorite potato crisp flavor?
105. If you were to die, would you prefer to be buried or cremated?
106. Suppose you were a secret spy; what would your alias be?
107. What is the longest time you’ve stared at someone without laughing?
108. What is the most creative insult you can think of?
109. Have you ever read your horoscope?
110. Ever counted the steps you take while walking?
111. When you were a child, did you ever make one of your parents cry?
112. Could you wear heels all day?
113. Is there a guilty pleasure you can’t resist?
114. Is there a musical instrument that you find the sound most annoying?
115. Imagine yourself as your own psychiatrist; what would you say to yourself?
116. Would you like to change anything if you become God for a day?
117. Do you remember any embarrassing moments from your childhood?
118. Have you ever greeted the wrong person?
119. If money and ethics were not an issue, what kind of experiment would you run as a mad scientist?
120. If you ever get trapped in a female body, what’s the first thing you’d do?
121. What was your dream job growing up?
122. When a baby is hungry, why do they cry?
123. How would you use your powers if you were Superman?
124. How would you indirectly insult someone with funny words?
125. What causes people to laugh when they see someone fall?
126. Whenever you run forward, you lose weight. If you run backward, do you gain weight?
127. If there is such a thing as the sexiest animal, what would it be?
128. What is the cutest nickname you’ve been called by a crush?
129. What is the most embarrassing dream you ever had?
130. Do you blow the punchline when telling funny stories?
Funny Questions To Ask A Guy Over Text
131. If you had to describe yourself in three emojis, what would they be?
132. What would you do if you could be invisible for a day?
133. If you were on death row, what would be your last meal?
134. What is the funniest picture you have saved on your phone?
135. What magazine would you like to be on the cover of?
136. Would you be able to survive a month without seeing anyone?
137. What’s the point of saying “after dark” when it’s really after light?
138. Do you remember the most awkward thing you did to get your crush’s attention?
139. Who would you want to be mistaken for if you were mistaken for an actor or actress?
140. What would be your preferred way of dying if you had the choice?
141. Do you sing in the shower?
142. What is your favorite word and why?
143. Who do you share a yellow heart with on Snapchat?
144. Have you experienced anything weird or funny this week?
145. What’s the funniest dad joke you’ve ever heard?
146. If you were born with a warning label, what would it say?
147. What would be your three wishes if you came across a magic lamp?
148. What’s the worst purchase you’ve ever had online?
149. If you were to have an animal sidekick, what animal would it be?
150. Which of your character trait are you most proud of and why?
151. Is there anything you’re weirdly afraid of?
152. How soon will you die if you can only eat the last thing you ate for the rest of your life?
153. Do you have a favorite meme?
154. Who is your favorite fictional villain?
155. Are you a horror movie fan?
156. What is the movie you have watched more than 10 times?
157. Do you know how to unblur Chegg?
158. Suppose you turned into a woman for a day. How would you act, and how would you spend your day?
159. Have you ever tried anything bad because of peer pressure?
160. Do you believe in a parallel universe?
Funny Date Questions To Ask A Guy
161. Have you ever been saved from an awkward situation by your sense of humor?
162. Have you ever experienced anything funny or bizarre on your first date?
163. Who would you call if you were trapped in a building and only had enough battery power for one phone call?
164. What is the worst thing a person should put in their dating app bio?
165. Have you ever been on a date and realized halfway that it was a bad idea?
166. Is there anything you would do if you could do anything without suffering consequences?
167. What’s the worst situation you’ve ever been in?
168. Are you a gamer? Any particular video games you’re addicted to?
169. Have you ever forgotten to bring your wallet when you were supposed to pay for a meal?
170. Ever had a bad experience while on a first date?
171. Do you have any strange talents?
172. Who is your ultimate celebrity crush?
173. Which would you prefer: being funny, smart, or sexy?
174. Did you have a funny childhood nickname?
175. Have you ever been in a life-or-death situation?
176. Have you ever done something crazy after getting really drunk?
177. Have you ever been moved to tears by a sad movie?
178. Do you like girls wearing make-up?
179. Do you remember a time when you laughed in an inappropriate situation?
180. Have you ever been told you’re someone’s dream guy by someone you know?
181. What is your opinion of online dating? Is it easier or harder?
182. How do you define a great date?
183. Have you ever lied to girls to get what you want?
184. What is the most ticklish part of your body?
185. How important is it to you to keep your promises?
186. Did you ever break up with someone over a text message?
187. Who has given you the coolest compliment ever?
188. What is your favorite romantic movie?
189. In a relationship, what is more important, compatibility or attraction?
190. How would you like to spend your date: on a beach or in an intimate setting?
Awkward Funny Questions To Ask A Guy
191. If you run out of toilet paper in the bathroom, what would you do?
192. What is the longest time you’ve gone without taking a shower?
193. What’s your worst habit?
194. Have you ever cheated on someone?
195. Did you ever have a secret relationship?
196. Do you believe in superstitions?
197. What is the worst thing you’ve ever done to someone?
198. Is there an ex-girlfriend you still keep in touch with?
199. Do you have any embarrassing stories about being caught by your parents?
200. Have you ever done something crazy after a breakup?
201. How many girls have you kissed?
202. Would you like to meet my parents?
203. Do you remember a strange thing a visitor did at your house?
204. What makes you blush?
205. Have you ever laughed so hard that your drink came out of your nose?
206. Do you have anything you’re afraid to share with me?
207. Have you ever passed out in public?
208. What is the closest you’ve ever come to dying?
209. In the future, when technology advances, would you consider giving birth?
210. Do you have any embarrassing pictures of yourself?
211. How good is your bathroom singing?
212. Can you tell me about the craziest and weirdest prank you’ve ever pulled?
213. What is the weirdest nickname you’ve ever been given?
214. What name would you choose if you had the chance to change it?
215. What is your new year’s resolution for next year?
Funny Inappropriate Questions To Ask A Guy
216. Do you make a lot of money?
217. How tall are you?
218. Are you sure you’re not gay?
219. Did you ever go without underwear for a day?
220. Why don’t you work out?
221. Do you think that plastic surgery might be a good option for you?
222. Have you ever been arrested?
223. On your phone, how many girls’ numbers do you have?
224. Can you afford the date?
225. Where is the strangest place you’ve gone to the toilet?
226. How did you end your relationship with your last girlfriend?
227. Are you interested in getting married?
228. Would you be willing to leave all your friends behind to be with me?
229. Can you tell me about the most embarrassing place you’ve ever farted?
230. When you’re with me, do you think about your ex?
231. Have you ever celebrated national ex-girlfriend day?
232. Do you want to have children?
233. Is there a time when you took money from your parents’ pocket or purse without their knowledge?
234. Am I more important than your mom?
235. How many girls have you slept with?
236. Going out for a girls’ night…Should I drunk-text you later?
237. When you were in elementary school, what was the dumbest thing you did?
238. Is there anything you have ever done that you consider unprofessional?
239. Are there any things you are terrible at?
240. Would you like to know what your future holds?
Dumb Funny Questions To Ask A Guy
241. If roses are red, why are violets blue?
242. Do you have an imaginary friend?
243. What is your most useless possession?
244. Do you think you can eat ice cream with your bare hands?
245. Do you enjoy breathing?
246. When we hear a funny joke, why do we laugh?
247. What’s the deal with square boxes for round pizzas?
248. How many sides does a circle have?
249. What color would you choose if you had to eat a crayon straight from the box?
250. Why don’t guys get menstrual periods?
251. What would you call a male ladybug?
252. Can a fish become dehydrated?
253. Can you move your nose or ears?
254. How is soup consumed? Do people drink it or eat it?
255. Where does a forgotten thought go?
256. If all animals could talk, which species would be the rudest?
257. What is your strangest habit?
258. Are mermaids able to have live babies, or do they lay eggs?
259. What is the best way to tell if a butterfly is male or female?
260. Is the sea salty because the shore doesn’t wave back at it?
Flirty Funny Questions To Ask A Guy
Try out some of these flirty questions with your crush or boyfriend.
261. Do you have a favorite snack besides me?
262. You’re still single. How is that possible?
263. Is there a perfect way to ask someone out?
264. Do you prefer to be called smart or sexy?
265. Is there anything you look for in a girl?
266. Before you go to sleep, what goes through your mind?
267. Which is more attractive to you… brains or beauty?
268. When someone likes you, how do they usually let you know?
269. When you are around someone, what makes you feel comfortable?
270. If you had to cook me a meal to impress me, what would it be?
271. Which is better – being naughty or being nice?
272. What’s your favorite pick-up line?
273. Would you rather kiss on your first date or wait until your second?
274. What is the first thing you notice about someone as soon as you meet them?
275. Are you more interested in casual dating or long-term relationships?
276. What would be the nicest thing someone could do for you?
277. When you wake up in the morning, what is the first thing you do?
278. What would you make me for breakfast?
279. Do you think there is any particular quality of yours that attracts girls?
280. When was the last time someone gave you a random compliment?
281. Do you have a belly button piercing?
282. Can you tell if someone likes you based on body language?
283. What do you like to do on weekends?
284. What do you do when you are home alone?
285. Would you accept a marriage proposal from a girl?
Funny Deal Breaker Questions To Ask A Guy
286. Can you still be friends with an ex, or do you prefer never to speak with them again?
287. Are you okay with your girlfriend posting candid photos of you on social media without your permission?
288. Would it be okay if a girl you like hates cats or dogs?
289. You noticed that you are dating someone who swears a lot; how would you handle it?
290. Your ex-girlfriend tries to communicate. Would you tell your current girlfriend?
291. Will you lie to a girl just to make her feel better?
292. How would you feel about your girlfriend still being close to her ex-boyfriend’s family?
293. What is your view on infidelity?
294. Is texting considered cheating?
295. Will you date a woman who doesn’t want to have kids?
296. Do you think it will turn you off if the girl you are dating is picky about what she eats?
297. Can you tell if a woman is a drama queen?
298. Would you consider dating someone from a different religious background?
299. How will you handle it if your girlfriend has a lot of guy friends?
300. Are you comfortable with girls who are very active on social media?
301. What are your thoughts on girls that are playing hard to get?
302. For you, what is the basis of a healthy relationship? How can you tell if it’s no longer working?
303. Would you date someone who smokes, drinks, and parties a lot?
304. What would you do if your mother disapproves of the girl you like?
305. Up to what extent can you tolerate dishonesty?
This list of questions should give you enough funny questions to ask a guy to make him laugh for a while. Having a playful conversation is a wonderful way to test his sense of humour and progress to a deeper conversation. Use this handy list of questions for couples, whether you’re in a committed relationship or just getting to know each other. Sharing an embarrassing experience or flirty text can spark fun conversations.