A good conversation can be tough. Especially when you want to be funny. Often, it turns out to be some awkward glances, weird chuckles, and nervous noises. If the same is your case, here’s the good news! We’ve got your back with some amazingly funny questions to ask.
Before that, let’s quickly see –
How do Funny Questions to Ask Someone Help in a Conversation?
Humor is a great element in having an impressive conversation. In fact, reports suggest that a good sense of humor is often linked to higher cognitive and emotional abilities. So, incorporating a fun element in your talks is definitely a good idea.
Now, the question is how? Starting a conversation right is the key. And funny questions can lead to this part easily. In brief, here are some ways in which these funny questions can add substance to your conversation –
- Funny questions lead to more positive exchanges of thoughts. Often, you’ll find it easy to discuss even the difficult matters by this approach.
- Humor makes the conversation more enjoyable and engaging. Usually, this brings the element of fun in a dull situation.
- Funny questions are great prompts for interesting small talks as well as meaningful deeper ones.
- It’s one of the easiest ways to improve your communication skills, especially if you easily get nervous or clueless in social situations.
- Plus, it helps in creating a more charismatic effect when done confidently.
So, now is the time to explore the funny list of questions that would make you shine in every conversation. Armed with lots of fun questions, 700 to be precise, this is the only list you’ll need. Feel free to use these –
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Funny Open Ended Questions
Questions prompting ‘yes or no’ replies are often the real hurdles to any quality conversation. So, what you need is a list of funny open-ended questions that can keep the chat going on. Have a look!
1. How would you describe spiciness to someone who has never tasted anything spicy in life?
2. If you had something written on your face, what would it be?
3. What was the most horrible-tasting dish you ever made?
4. Can you share the lamest funniest joke you ever heard?
5. What was the best excuse you ever made for not attending a class at school that solved the situation?
6. Have you ever waved at someone to realize later that they are the wrong person?
7. What is one completely useless thing that you can spend hours doing?
8. Can you share your biggest DIY fail story?
9. What was the most embarrassing thing you did in public transport?
10. Describe the funniest thing you’ve seen someone doing in Walmart.
11. What would you do if you got invisible for a day?
12. Describe the funniest smell you have ever smelled.
13. When was the last time you got super mad at someone? And why so?
14. What was the smartest lie you ever told? You’re not lying now, right?
15. If you could charge a million dollars for a service provided by you, what would that be?
16. What was the most ridiculous lie someone said on your face?
17. Name one thing you possess that you absolutely refuse to share.
18. Suppose you meet your ex after a really long time, what would be your first reaction?
19. What was the craziest thing you have ever written in your answer sheet?
20. Give one example of your super laziness.
Funny Questions to Ask Friends
Planning a fun time with your friends? Maybe a pajama party or a weekend chill plan. But unsure about how to make it more entertaining and personal? Some funny questions to ask your friends always come handy! Here are some great questions for you –
21. If you could make a tv show that is about your best friend’s life, what would you name it?
22. For how many days can you do fine without taking a shower? And what about staying without brushing your teeth?
23. What was the most exaggerated yet supposedly true story you ever heard?
24. What was the dumbest answer you ever gave in an oral exam in school?
25. Can you describe the craziest person you ever met, enough for our guessing, without naming the person you’re talking about?
26. Who is most likely to be a psychopath among your friends?
27. Can you give 5 points to support that you are dumb?
28. What was the craziest proposal you ever got?
29. If you could eat food for the rest of your life only when you do something productive, what are the chances of your survival?
30. Have you ever eaten a cookie that fell on the floor?
31. What is your favorite slang?
32. How would you react if you find out that your best friend has a secret crush on you?
33. If you could either be in a swimsuit or in an over-stylish suit for the rest of your life, which one would you choose?
34. Which tv-show plot do you find horribly illogical?
35. Suppose you are the monarch of a country, what would be the national emblem?
36. If you had to add an animal’s face on your body, everything else remaining the same, which animal would you choose?
Funny Questions to Ask a Girl
Do you often get nervously clueless when it comes to talking to a girl? Well, making her laugh is something that almost always works! So, add these fun questions to ask a girl in your conversation and make things better –
37. What would you choose if you have to leave one – eyebrows or eyelashes?
38. If you could change the color of your eyes to anything that doesn’t look natural at all, which color would you choose?
39. What is the poorest grade you ever scored in an exam?
40. If you could live anywhere in the world but naked all your life, where would you live?
41. Did you ever get too drunk to even remember your name? Or else, what was your craziest drunk experience?
42. What was the weirdest outfit you ever had?
43. If smells had colors, what color would your smell have?
44. What is worse during a kiss – a sneeze or a burp?
45. Did you ever visit a place in a completely inappropriate choice of outfit?
46. What would you choose to be reborn as – a human or an amoeba?
47. What would you prefer to be called if you had to choose one – a tomato or a potato?
48. Have you ever written a love letter to someone?
49. What is the one tip that always works if one wants to make a girl laugh?
50. If suddenly people could read your mind but can’t read theirs’, how would you react?
51. What are the dumbest main lead fictional characters you’ve ever seen?
52. Did you ever disclose someone’s secret that you promised you wouldn’t?
53. What was the dumbest thing you did in a restaurant?
54. Share your dumbest school experience.
55. What was your most daring step ever?
Unsure about what questions would make him interested in the conversation? Or, is it just that you need some ideas to ignite a boring chat with him? These funny questions can do the trick!
56. Can you describe your crush’s sexy traits keeping it SFW?
57. If you could get the power of hearing what a person is thinking, but this applies to one person, whom would you choose?
58. Can you touch your nose with your tongue? Prove it.
59. Suppose your crush turns out to be a vampire. Would you feel butterflies or get afraid when she comes to you?
60. Which fairy tales do you find most ridiculous or utter nonsense?
61. How do you describe your face using vegetables for reference?
62. What are the craziest pizza toppings you ever tried?
63. Can you think about a song that is perfectly unsuitable to propose to a person on a date?
64. What one normal thing becomes weird if you do it more than once, back to back?
65. If you could create a new fashion accessory that should essentially make people look crazy, what would it be?
66. What weird kind of sound can you make?
67. Do you think it’s a good idea to be able to sleep whenever and wherever you want?
68. What is the weirdest food combination you can think about?
69. Hair or teeth – what is more important to look good?
70. What one song or music is your ultimate definition of annoyance?
71. How many animal’s sounds can you make? Show!
72. What is the most useless gift you ever got?
73. If you had to choose between constantly wearing dark red lipstick for a week or walking in heel sandals for the same time, which one would you choose?
Questions to Ask When You Don’t Know What to Say
When you’re completely clueless and off the track, these funny questions will help you guide the chat. Explore!
74. Who is the dumbest celebrity according to you? And why do you think so?
75. Can you share a secret talent of yours that can make others feel jealous of you?
76. If you had to, what crazy name would you choose for your kid to make them embarrassed for life?
77. What was the dumbest way in which you hurt yourself ever?
78. If you had to create an unconventional dumb and weak protagonist for a video game, what would it be like?
79. What is the weirdest face you can make? Do it now!
80. If you could change one thing about human anatomy, what would be that?
81. What was the weirdest hobby you ever heard about?
82. If you could change one thing about any of your favorite sports to make it funny, what would you do?
83. What do you think is the quickest way to hurt someone’s ego? Is it enough to hurt your ego too?
84. Can you offend someone without doing anything offensive? How?
85. When was the last time you skipped a shower? For how many days?
86. How many times do you wear a t-shirt before washing it?
87. What one thing you used to do thinking it looks sexy but later found out the opposite?
88. Did you ever try something too confidently but failed miserably?
89. What do you think is better – funny or sexy?
90. Zombies or super heros – which seem more exciting to be real?
91. What is the one thing that movies never get right?
92. Describe the worst tasting food you ever had. Would you have it daily all your life for 1 million dollars?
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Funny Questions to Ask Siri
Not always you need some funny situations to have a good laugh. Sometimes, asking some simple questions can be quite funny. Especially, when you’re asking Siri. If you don’t know, Siri is a virtual assistant based on AI that is a part of Apple Inc.’s operating systems. Here are some good questions that Siri answers in it’s iconic ways!
93. Can you tell who created you?
94. Hey Siri, what is zero divided by zero? (As a quick glimpse, it’ll get a bit wild with zero friends you have and zero cookies left concluding how the cookie monster is sad).
95. Do you consider yourself smart?
96. Hey Siri, do you know the three laws of robotics?
97. Why are you so serious?
98. Explain the Matrix movie.
99. I’m your mother.
100. What do you eat?
101. How much wood would a woodchuck could chuck if a woodchuck could chuck wood?
102. Why would chicken cross the road?
103. Do you believe in ghosts?
104. What is life?
105. Are you a theist or an atheist?
106. Hey Siri, do you know Alexa?
107. Who stole the cookie?
108. Tell me a joke about Chuck Norris.
109. What makes you vibrate?
110. Siri, can you beatbox? (Now, you have to relax while Siri would simply repeat ‘boots and cats’.)
111. Can you recommend a good smart speaker?
112. What are you made of?
113. Siri, are aliens real?
114. Do you like me?
115. What would you like to eat?
Funny Questions to Ask Alexa
When it comes to quirky replies, Google’s AI voice assistant – Alexa is not at all behind Siri. Even simple questions can bring some hilarious responses that would make anyone laugh. Try it yourself with these amazing questions-
116. Alexa, roll a dice.
117. Tell me the magical words.
118. Alexa, tell me a yo mama joke.
119. What does Alexa mean?
120. Alexa, which is the best voice assistant?
121. Can you tell how old are you?
122. How do cats speak?
123. What is the best pickup line you know?
124. Chicken or the egg – what came first?
125. What’s the right choice – blue pill or red pill?
126. Can you tell a weird story?
127. What will you be when you grow up?
128. Alexa, do some rap for me.
129. Can you flatter me?
130. How is Cortana?
131. Alexa, tell me a secret.
132. What did you dream about?
133. Alexa, when are you free?
134. Can you explain the movie Inception?
135. What would you like to eat?
136. Am I looking fine?
137. If I get another amazon echo tip or amazon echo dot, the AI personal assistant coming in echo deals would be you or your sister?
138. How does it feel if you step on a lego?
Funny Questions to Ask Your Girlfriend
Looking for something to make your girl laugh? We’ve got you some amazing questions here!
139. If you could read someone’s mind for once, when would you use your power?
140. What is my one weird habit that you find sexy?
141. Did someone ever treat you with food that you had a hard time finishing?
142. When was the last time you wanted to punch someone?
143. Did you ever get happy finding that I too hate the person you hate secretly?
144. Can you make the ugliest face saying the sexiest pickup line you can think about?
145. If you have to boast about having a sexy boyfriend, how would you do it?
146. What is the cutest dirty animal?
147. Share your kinkiest dream date idea.
148. Do you have a crush on an anime character?
149. What is your favorite dirty joke?
150. Did you ever overhear someone bitching about you on your back?
151. Would you prefer to be the pretty villain or ugly princess?
152. Suppose your doppelganger cones here claiming to be you. How would you prove the truth?
153. Who is the one person whom you would never want me to hang out with?
154. Tell the cheesiest line you can think about.
155. If you could tell one thing about you that would scare off any person hitting on me, what would it be?
156. Did you ever create a rumor, intentionally or unintentionally? What was that?
157. Tell me one crazy fact about you that you never told me.
158. What was the first thought that came to your mind on our first encounter?
159. If I were a food, what would I be?
160. Did you ever want to curse and hug me at the same time?
Funny Questions to Ask Your Best Friend
Bored? Here’s the fun. Ask these bone-tickling questions to your best friend for some funny chill moments –
161. What was the dumbest thing I ever did according to you before we started dating?
162. What was the most cringeworthy moment you ever had?
163. Did you ever try helping someone that got all wrong?
164. If you could create a non-human fiction character that suits me, what would it be?
165. Did you ever skip brushing your teeth for a day?
166. On a scale of 1-10, how lucky are you?
167. If you had to design an unconventional auditorium, where would you make the audience sit?
168. Did you ever pretend not to hear someone’s calling to avoid work?
169. How lazy are you?
170. You are dumb and I come to you to get my problems solved. So, who is dumber?
171. What will you do if you find a skeleton in your closet?
172. How many times do you open your refrigerator without any purpose?
173. Who is cuter – me or seagulls?
174. How often do you eat just because your mouth is lonely?
175. What makes you sexy?
176. Suppose you have to ruin someone’s day by saying something crazy. What will you say?
177. Who is one person you can trade for a bag of chips if you had to?
178. Prove you are smart in the next 1 minute.
179. What is steamier than a piping hot soup?
180. Tell me anything about you that I won’t believe.
181. If your life was a movie, what would you name it?
182. Suppose you randomly ran into God. What would you tell God?
183. What is better – a rose or a potato?
184. If you had to name a country, what would you name it?
Funny Questions to Ask Someone over Text
Some fun doesn’t always need a face to face chat. A text with some fun and quirk can make you laugh too.
185. If you had to start a rumor, what would it be?
186. What one invisible thing you wished was visible?
187. Did you ever play dumb to avoid work?
188. What is the creepiest message you ever got?
189. Why is a burger not a sandwich?
190. Do you like pineapple on pizza?
191. What was your first email id?
192. Can you share your useless super powers?
193. Tell me the weirdest fact that ruined your day.
194. What flavor would be the funniest to add for an ice cream?
195. If you could cosplay in the birthday party of the meanest person you know, what character would you play?
196. What gift would you pick for your enemy?
197. If you had to, what kind of secret society would you begin?
198. What is the strangest place you had to spend your night?
199. If you could swap one thing in real life from social media, what would it be?
200. When was the last time someone left you on reading?
201. If you could turn an embarrassing action into something pleasant in people’s view, which action would you choose?
202. What is the weirdest excuse someone gave you for not texting back in time?
203. Can you make yourself seem like a psychopath by just one text?
204. Who is one person who is most likely to be a serial killer?
205. Aliens or ghosts – what seems to be more realistic?
206. If you could detach one of your body parts, which one would it be?
207. Have you ever called someone with a weird name publicly mistaking them to be someone else?
Funny Questions to Ask People
Done with boring talks? Now, let’s explore some funny questions that you can ask anyone in any casual situation.
208. Did you ever try to look cool showing off your sporty skills and made a fool of yourself in the end?
209. What one outfit can you wear in public to piss most people? Did you try it out?
210. What one thing can you ask for in a grocery store to get the weirdest look?
211. Which is the song that you secretly like but don’t tell others because it is weird?
212. If you could have one useless superpower, which one would it be?
213. What one thing someone used to do for you thinking you liked it while you secretly hated it?
214. Suppose you won the lottery of 1 million dollars, but you have to use it in a single day, how would you use it?
215. What is the craziest conspiracy theory you have ever heard about?
216. Which sport would be the funniest if it had to be played with blind eyes?
217. If you have to insult someone what is the most creative insult you can think about?
218. Which work is so terrific to you that you would rather beg than do it?
219. Did you ever have an embarrassing victory? What was it about?
220. What is the best thing to use as a replacement to toilet paper?
221. According to you, which animal would be the most sarcastic one if it could talk?
222. Which is the scariest children’s movie, according to you?
223. Tell a joke which isn’t funny but can make you laugh.
224. What unwritten rule is there to be safe around you when you are super angry?
225. Can you tell me something that annoys you?
Silly Questions to Ask
You don’t have to be always smart. Often, silly is funny!
226. What is the one thing that people consider trashy but you find classy?
227. As a guest, how weird can you be?
228. What is the most freaking or weird thing you saw in someone’s purse?
229. If you have to call an apple anything but an apple, what would you call it?
230. How would you feel in a world where people would actually start singing and dancing out of nowhere like in musicals?
231. What is the craziest business you have ever heard of?
232. Can you share one habit of yours that you found cool as a teen but now even it’s memories embarrass you?
233. Add a mandatory amount of alcohol
234. Can you tell something in 5 seconds to make yourself look like a total weirdo?
235. What was the most insulting compliment you ever got?
236. Did someone ever help you in a way that ruined things for you?
237. Which inanimate object do you think would be dumbest if it had life?
238. If you had to eat either grass or grasshopper, which one would you choose?
239. Who do you think would win if a dog and a cat could have a debate?
240. Suppose you are running in a race and suddenly it is announced that the ending and the starting points are interchanged. Besides, you have to reach the starting point instead of the end point to win. Now, would you have to change your direction or not?
241. Which is more tiresome – brushing your teeth or taking a bath?
242. Tell me a fact that you secretly consider a conspiracy theory.
243. If you had to choose one – would you always speak truth or always lie?
Ridiculous Questions to Ask
Are you up for some fun? Here are some ridiculously funny questions to tickle your bones plus make others laugh! Let’s explore –
244. Zombies or vampires – whom would you like to have dinner with?
245. Like Spiderman, Batman, and Ant-Man, what kind of wo/man would you like to be with your special powers?
246. What do you think would make food more hard to eat – over salt or over spiced?
247. Can you distinguish between the tastes of – wooden, iron, and plastic chairs? How?
248. What is the craziest bet you have ever lost?
249. Did you ever eat something that was inedible?
250. Would you like to have the power of photosynthesis with the condition that you can never have food like you do now?
251. Which Disney villain deserves to be the main protagonist?
252. Name the Colorado that you just find boring.
253. Chilled water in winter vs hot water in summer – what would you choose to have a bath?
254. From whom the first person ever bought the land that started the whole process of buying and selling lands?
255. In a zombie apocalypse, if a kiss could make those zombies humans again, would you do it?
256. How do other fishes know when a fish cries underwater?
257. If animals could talk, which animal would you like to talk first?
258. Do you think hummingbirds hum because they are too lazy to speak?
259. Are there any crash courses for pilots?
260. Suppose you reached a deserted island and stuck there. Now, would you prefer meeting someone there who might turn out to be human-eaters (or might not), or prefer to be alone without anyone around?
261. If you could have a secret affair with any of the celebrities, who would it be?
Funny Questions You’ve Never Heard Of
Bored with the same old repetitive questions that don’t even sound funny now? Let’s try new ones you’ve never heard of. Which are bound to make you smile!
262. Why is lipstick called lipstick when it doesn’t stick your lips together?
263. If you could get a remote control of anything in the world, what would it be for?
264. Suppose you get to know that you are a character of a comic book and you run into the writer. Now, what would you do?
265. How would mermaids choose a foundation for themselves since they have two kinds of skin?
266. What makes New Zealand new?
267. Isn’t poison the most effective sleeping pill?
268. Why is it called life insurance when it is given after one’s life ends?
269. We can say something cold as chilled but chillies are called hot. Why?
270. If running cars too fast is illegal, why are cars made to run that fast?
271. Why do vampires suck blood when they can just have some Vitamin D supplements?
272. Can a bedroom be a bedroom without a bed?
273. How is SpongeBob SquarePants while it’s parents are round? Does it mean it is adopted?
274. Would you like to have you as your love interest if another version of you comes from the parallel world?
275. Tell a joke too intellectual to understand.
276. How would you react if you see a huge fly on the wall beside you when you lazily open your eyes from sleep?
277. Would you choose to wear an outfit made of ingredients of a cake or eat a cake made of a fabric?
278. Horn or tail – what would you choose if you had to?
279. If you were a brand, what would be your brand tagline?
Dumb Questions to Ask People
Are you the one who has got some smart answers even for stupid questions? Then try your hand in these –
280. Is cereal soup?
281. What is your secret stupid fear?
282. Tell me your absolute worst secret.
283. If your phone could talk, what is the worst thing it would reveal about you?
284. What do you do in your leisurely good time?
285. How many ants would you need to kill an elephant?
286. What is the most annoying noise you can make?
287. If you take a challenge of losing a game but you win, then are you a winner or a loser?
288. Okay, if violence is not the answer, is it the question?
289. What is something that has a funny smell yet you sniff it nevertheless?
290. Suppose you can win a lottery if your enemy can win the double of the amount. Will you go for it?
291. What is the weirdest thing you spotted at someone’s house?
292. You are banned from entering a country. Why would it be?
293. What is the craziest hairstyle you have ever seen? Did you try it?
294. What is the one weird unwritten rule at your home?
295. Tell me what makes you perfect for mental asylum.
296. An old tattered thin outfit or best fitting new undergarments – which one would you choose to wear to roam around the city?
297. If anything could fall from the sky instead of rain drops, what would you choose?
298. What is the most embarrassing moment you have experienced being you?
299. If you could replace easter eggs with something else, what would be?
300. If you have to name yourself again making it sound like you were in a hurry while choosing it, what would it be?
Crazy Questions to Ask
Questions that sound crazy and make you feel like a stoner. What can be funnier than these? Let’s dive deep!
301. Can you do something to prove you have a good sense of humor?
302. Which mythical creature would improve your life if you had it?
303. If there were stupid parking spaces like handicapped parking spaces, how would you prove your stupidity to get the space?
304. What was the dumbest thing your friend did to help you but ruined it further?
305. Have you ever seen a piece of art that made you doubt the taste of artistic people?
306. Which animal resembles your personality most?
307. Have you passed on a gift to someone that you got from some else?
308. Do you sleep hugging stuffed animals?
309. What one breaking news you saw in the news that made you question what news is?
310. Did you ever crave for or actually try your pet’s food?
311. If you reach a desert island and find that they have society just like yours just they don’t have the concept of clothes. So, would you also abandon clothes or would you show its use to others?
312. Did you ever receive an awful gift but you pretended to like it?
313. How do people in movies look all sexy and stuff when they wake up in the morning?
314. Did you ever stalk someone online?
315. What are the good habits you have that people consider as bad habits?
316. How does it feel when you step in an elevator and someone is already there with eyes fixed on you?
317. What do you do when others are singing ‘happy birthday’ to you? Do you sing along, clap, or stand there like a clown with an awkward smile?
Funny Questions to Get to Know Someone
Want to know more about that person? Try these funny get to know me questions while making them laugh!
318. What makes you cool?
319. How would you introduce yourself to your crush?
320. What was your most embarrassing experience at a convenience store?
321. Have you ever been to a book show of a writer you have never heard of?
322. Can you survive a week without your phone?
323. Have you ever been thrown out of a place, like class, club, someone’s house, etc.? Why?
324. Did you ever skip from school?
325. Would you get embarrassed if your roommate tells you that you grind your teeth in sleep?
326. If your favorite movie completely changes its plot but it’s characters aren’t the same, would you still like it?
327. What one thing do you do that you pretend to hate in front of others?
328. Tell me your one personality trait that doesn’t match with what people generally think about you.
329. Among everyone sitting in the room, rate everyone’s senses of humor.
330. Do you know someone who is completely harmless but gives a dangerous vibe?
331. What is the most horrific story you ever made as a child?
332. Where do you not see yourself in ten years?
333. Tell me your most irrational fear.
334. What is the one thing that you can share with a stranger but not with your parents?
335. Can you share your WIFI password?
336. How often did you get annoyed today?
337. Have you ever been intentionally mean but people thought you were funny?
338. If you fall in love with a vampire, would you volunteer to give a little blood to them regularly?
339. What is the worst song you are addicted to?
Funny Random Questions to Ask People
Why plan everything when random is fun? Yep. Try these random questions to ask a guy or girl
340. Do you talk to yourself loudly?
341. Do you scream in your head when frustrated but can’t do anything?
342. Tell me your one odd flex.
343. Can you share the plot of any one of your favorite movies in one sentence?
344. What is the cutest threat you ever got?
345. Is there something that your friends would warn me about you if we start dating?
346. How would you describe an alien, why do humans show aliens as some kind of villain in movies?
347. If your Google assistant could tell others your biggest secret, what would it be?
348. Did you ever have an experience when there was delicious food in front of you but somehow you couldn’t eat though you wanted to?
349. What is the one thing you want to invent or create if you could?
350. If you had an unconventional website, which had affiliate links to things one can buy with a special currency, what would it be made of?
351. How would you feel if your friend passed the test copying your paper but you failed?
352. What was the most horrific children’s book you ever read?
353. Did you ever try touching your nose with your tongue?
354. Can you see your nose? Even the tip?
355. Which stupid thing you love to do?
356. If you could be an elf for 24 hours or turn into a bird, what would you choose?
357. If you had to replace your nose with anything, what would it be?
358. What is more embarrassing – revealing your browsing history to your friends and family, or accidentally getting your clothes torn in a public transport?
Funny Questions to Ask Friends when Bored
Your gang is up for a fun time. So, make things more exciting!
359. Suppose you are challenged to get yourself admitted in a mental asylum by proving you have some mental issues. How would you prove that?
360. What inanimate object would you choose to be if you have to be one for a year?
361. IQ (Intelligent Quotient) vs EQ (Emotional Quotient) – which one would you like to exchange yours with me?
362. What would happen if our nails are replaced by our teeth and vice versa?
363. Sneezing vs hiccups – what is more embarrassing in a formal meeting?
364. If you have to convince a prosecutor that you are a criminal and you can choose any crime you want, how would you do it?
365. Can you wink and whistle at the same time?
366. What is the weirdest hair colour have you ever seen?
367. If you had to choose something from daily life to be added in the Olympics as an official sport, what would it be?
368. Can you show some dance moves that express your mood now?
369. What one thing that superheroes wear you find wild?
370. Do you think it would be sexy if humans would sniff each other as a form of greetings?
371. If you could design an amusement park that is very different from the regular amusement parks, how would it be?
372. What is the coolest phone ringtone you have ever heard?
373. Name one famous person who you aren’t sure why is famous.
374. Do you know someone who acts coy but is dirty?
375. What is your favorite 80’s style that is weird yet cool?
376. Do you think you would get along with your clones? Or would you fight among yourselves for leadership?
Interesting Questions to Ask Someone
Questions are perfect entertainers. So, try these interesting questions to ask a guy or girl when you want to have some fun time –
377. If you meet an attractive ghost, would you date them?
378. Who is one person who is a walking red flag but you act colorblind for them?
379. Is there a wrong thing that sounds right?
380. What dumb thing does your crush do that you find sexy?
381. Did you ever resign in a badass way but had to rejoin the place?
382. What is one fashion trend that is so cringy that you wish it would have never come?
383. Do you think you would be allowed in a club which only allows ‘sexy’ people?
384. What is a ‘pain’ food but addictive and delicious?
385. Potato or eggplant – what defines your personality more?
386. If you could apply slow motion in real life, when would you do it?
387. And when would you use the fast forward option in real life, if you could?
388. Do you think the person who named the fear of long words as ‘hippopotomonstrosesquippedaliophobia’ wanted to take some revenge on people with this phobia?
389. If there exists fast food, what is slow food?
390. Which operating system fits your personality most?
391. Do you think that by making children read about wars in school, we teach kids that violence is the answer?
392. What is your favorite Disney cartoon character which is not liked by most people?
393. Can you tell one ‘old people’ thing that you do?
394. Which intelligent assistants in movies deserve to be the main characters?
395. Are there any favorite foods that you used to love as a child but now hate?
396. What is the most interesting conversation you ever overheard?
Funny Questions that Make You Think
Not all thoughtful questions are serious. Some can be more than funny. Like, these here –
397. If you could design a smart home with any technology, real or imaginary, how would it be?
398. Suppose your enemies earn a commission when you buy anything you love. Would you still buy it?
399. If your traits could be sold by ‘buy through links’, which traits do you think would people buy?
400. Do you think someone mixed the names of Iceland and Greenland for fun and forgot to correct it?
401. Why is it called tap though you don’t need to tap on it?
402. Do you think death is a good thing since logically all the sorrows of the dead person end there?
403. Why is pizza round but pizza box square?
404. Do you have someone with whom you’d like to get stuck in an elevator? Can you tell them?
405. What do you think is the logic behind having buttons on different sides of shirts for men and women?
406. Do you think wearing clothes is really useful when we have to wear those even when they make us uncomfortable?
407. Why do we associate the heart to emotions though all it does is pumping blood?
408. How did people start translating for the first time when they didn’t know each others’ language?
409. What if breathing is not needed for life but we are just so addicted to breathing that we die as a reaction to stop it?
410. Don’t you think marriage is a kind of business?
411. What is the main reason to eat – taste or survival? Like, would you abandon eating delicious food if you could survive without eating?
412. Smell like butter or have green colored sweat – what would you choose?
Funny yet Deep Questions to Ask a Guy or Girl
How about a conversation that is deep yet funny? Yep. Here are some deep questions to ask a girl or guy when you want it to be funny as well!
413. If you were a place, when would be your tourist season?
414. Why is fast food called fast when actually it helps us not fasting?
415. Nosy roommate or noisy roommate – which one would you choose?
416. Do you think a perfectly healthy relationship is boring because it is just too perfect?
417. Why do you think we assume that a life partner needs to be someone romantically involved with us?
418. Name one historical figure who would totally rock in current times.
419. Shaved head vs shaved eyebrows – what would you choose to have for your whole life?
420. If you’re a villain, which ‘superhero’ character would you choose against you?
421. Suppose you can hire any fictional or historical character as your personal assistant. Whom would you choose?
422. Food that looks like dirt or tastes like dirt – what would you have if you had to?
423. Can someone get sexually attracted to themselves if their clone from the parallel world appears?
424. Do you think you can survive without your smartphone for the rest of your life?
425. What is the most annoying sound one can hear in the morning?
426. So, why do you think farting is embarrassing when it is a natural bodily function?
427. Did Noah have woodpeckers on the ark?
428. What is the wildest thing you wrote as a child?
429. Tell me one thing about you that others would warn me about.
430. What one thing about our world do you think an alien would find totally weird?
431. If you ran into God randomly, what would you do?
Weird Questions to Ask a Guy or Girl
A good conversation starts with a good question. Weird can be more than good when it’s about making you laugh. So, let’s explore some good weird questions!
432. Do you like cursing?
433. Describe your life in a movie title.
434. What one thing you can not do that will improve the world?
435. If you get a chance, would you like to be a ghost hunter?
436. What was the most savage reply you got from someone least expected to say so?
437. Do you think hate is a form of love?
438. Why do you think humans are scared of ghosts even though we don’t really know anything about them if they do exist?
439. Depending upon your personality, what do you think would be your perfect murder ṣweapon?
440. Are eyebrows facial hair?
441. How would police handcuff a criminal who has no arms?
442. Why do they make sandwich meat round when bread is square?
443. Do you think you are an annoying person? Why or why not?
444. If you could trade your intellect for money, would you do it?
445. When did you think exactly time began?
446. Are there any flat-Mars or flat-Sun societies? Since there are flat-Earth ones.
447. What human invention do you think did more harm than good?
448. Fame or money – what do you think makes you a celebrity?
449. What doesn’t make sense but feels right?
450. How do we get titles like ‘Highest IQ’ or ‘Tallest person’ in the world when we can not reach each and every person in the world?
451. Do you think you’d be able to develop everything again if you had to survive in ancient times?
452. What would you do if you could replace your index figure with a chopstick?
Questions that Give You a Hard Time Answering
Too confident? Here are questions that would make you speechless while making you laugh.
453. How do you know that this is not a dream?
454. What one thing you find really boring that others find interesting?
455. If you had to replace toilet paper with something else for the rest of your life, what would it be?
456. Why do we call people ‘Sweet tooth’ when we actually taste sweetness with our tongue?
457. Do you think an apple watch is a better deal than the lifetime supply of the fruit apple?
458. What color annoys you?
459. Have you ever eaten something and later found it wasn’t edible?
460. What was the most inappropriate situation in which you farted?
461. Did you ever keep a gift that was not meant for you?
462. What funny response can one give everytime you call their name?
463. A food bouquet or a flower bouquet – which is better?
464. If there was a real death website that mentioned ‘links on our site can take you to hell’, would you click on the link for fun?
465. Do they nail down a coffin’s lead so that the dead person can’t escape even if they could?
466. Why do we call cheaters as dogs though dogs are most loyal?
467. Can you explain what ‘okay’ means?
468. If driving a car at a speed more than the recommended scale is illegal, why do they make it to be able to run at that speed?
469. How is glue effective when it doesn’t stick inside the bottle?
470. If nobody is perfect, why do we say that practice makes perfect?
471. How slow do cold cakes sell as compared to hot cakes?
472. What do you call the earthquakes that occur on the moon?
Let’s jump to some nonsense questions now without another word because it is not supposed to make sense anyway!
473. How do you know that when your pet is speaking to you, it is not cursing you?
474. Smelly fingers or runny nose – what would you choose if you had to?
475. Why do they say that everything comes from nothing when nothing is clearly nothing?
476. How do you know you are dead when you are dead?
477. Do you think pets gossip about the owners among themselves?
478. Why can’t we say that a circle is a rounded-up square without corners?
479. If animals can survive without clothes, does that mean clothes are not a part of basic needs?
480. We know about the Big Bang Theory but what about the Small Bang Theory then?
481. Do we call orange orange because it’s color is orange or do we call orange orange because the fruit orange is orange?
482. If we all are different, does that mean we all have the similarity of difference?
483. What if dreams are real and what we consider real is a dream?
484. Is hunger the thirst for food and thirst the hunger for water?
485. When violence is not the answer, what is the question?
486. If you daydream at night, is it called nightdream?
487. Why do we say face and body when face is also a body part?
488. If beauty lies in the eyes of the beholder, where does the beholder lie?
489. Why do our nails grow again after cutting but not our limbs?
490. If a spy is spying on another spy who is spying on him, would they catch each other?
491. Who decided an hour is an hour for the first time?
Not all questions have answers. Nevertheless, they can be entertaining and fun. Let’s explore some of such ironic questions –
492. If you wish a good luck for business to a coffin-maker, are you wishing bad-luck to someone else?
493. Do you think a mirror has a color?
494. Why do they call it a boxing ring when it is square in shape?
495. Do they make deer flavored tiger food?
496. Isn’t it weird that doctors refer to what they do as ‘practice’?
497. Can blind people see in their dreams?
498. If someone tells you that they always lie, are they telling the truth or lying again?
499. What is the synonym of synonym?
500. If a synchronized swimmer drowns, do all the swimmers drown?
501. When we expect the unexpected, does it mean we are actually expecting the expected?
502. Do you think the word ‘phonetic’ is phonetic?
503. Why do we call money brokers a ‘broker’ when they are meant to save and invest our money?
504. Do you find clowns funny or scary?
505. If the world is unfair for everyone, does it make it fair?
506. Does poison expire?
507. Why do they make paper pamphlets of save paper?
508. Can a fish get thirsty?
509. Would you like to wear black in your funeral or something else to stand out from the crowd?
510. If the super hero becomes the villain, who would save the world from them?
511. Why do we call it cargo and not shipping when ships carry it?
512. If a bug hums, should we call it humbug?
513. Why do the ‘piece of cake’ for something easy though it takes hard work in baking a perfect cake?
514. Can you stay a minute without thinking anything including this that you won’t think anything?
515. Why does Superman wear the underwear on the pants though it is clearly an ‘underwear’?
516. If a donkey is stupid, what do they name call it?
517. Why does look and see can be often used interchangeably but not overlook and oversee?
518. Do people with amnesia remember that they have amnesia?
Would You Rather Questions
So, you want something that is funny and interesting. Plus, it should lead to long talks. Then, this list of ‘would you rather questions’ is the perfect pick for you. Let’s explore –
519. Would you rather always dress like a clown or sound like one?
520. A tree or a robot – what would you choose to be?
521. Would you rather always sound annoyed or never sound serious?
522. An amazing date with a jerk or a dull one with a loyal person?
523. Would you have your life as a funny story or a melodramatic one?
524. Homeless but a good toilet facility or good home but had to go outside for poop and pee?
525. Would you rather crawl for the rest of your life or bark whenever you speak?
526. Sweet or spicy?
527. Would you rather have great food or great sex?
528. Have a monster or be a monster – what would you choose?
529. Would you rather travel all your life without a home or have a home and never leave it?
530. Have chopsticks as your fingers or spoon as your thumb?
531. Would you rather see everything in super fast mode or in the slow-motion mode?
532. Get treated like a dog or be a dog – what sounds better?
533. Would you rather be a successful criminal or a failed cop?
534. Happy dumb or sad smart?
535. Would you rather eat grass or drink oil?
536. Have one true love but never live with them or have a new love everyday and live with them?
537. Stuck with your enemy in an elevator or stuck alone there?
538. Would you choose to be a weak hero or a strong villain?
539. Never being able to laugh or never being able to cry?
Funny Questions To Ask your Crush
Up for a great time with your crush? These funny questions will help you rock it well!
540. What would be your flavor if you were a pizza topping?
541. Saving money or spending money – what do you find more thrilling?
542. What is the weirdest date you have ever been on?
543. Can you give 5 reasons why I should date you?
544. What is your pickup line that you use for hitting on someone?
545. Cute or sexy – what kind of people do you like more?
546. What one clear hint you give when you’re interested in someone?
547. Are you the jealous kind of girlfriend/boyfriend?
548. Would you wear a T-shirt saying Sexy to your workplace?
549. Do you get nervous before someone you like?
550. Tell me one thing that I don’t know about you.
551. A romantic movie or a horror movie with your date?
552. Would you like it if someone confessed now that they have a crush on you?
553. Rate how ‘romantic fool’ you can get for your loved one, on a scale of one to ten.
554. What was the most embarrassing misunderstanding you ever had?
555. Do you easily blush?
556. What can make you happy almost every time?
557. Do you believe in soulmates?
558. How likely are you to fall for someone like me?
559. What is your kind of humor?
560. Do you have any secret superpower?
561. If you had to choose between being a sexy devil and an ugly angel, what would you choose?
562. Can you show how good your flirting skills are?
563. Do you still find your first crush attractive?
564. Is there something you hate being asked?
565. What is the dumbest thing you used to believe as a child?
Questions to Get to Know Your Family Better
Your family time is one of the most precious things you can have. And you can make this warm family reunion more fun with these meaningful funny questions. Let’s dive deeper!
566. Were you a fussy eater as a child?
567. Did you ever play a prank on your family member that you want to share?
568. What was the wildest thing for which you have ever spent all your pocket money?
569. Can you tell the most embarrassing name you got at your school?
570. Among all of our family members, who is most likely to be a hopeless lover?
571. What one thing I used to do as a teen that made you all troubled?
572. Did you ever tell a funny lie to all of us that you want to confess now?
573. What did I ever tell a child that freaked you all?
574. Are you having any secret love affair now?
575. What is your funniest childhood memory?
576. Do you remember any incident when we fought like crazy?
577. If you could rate all of us from crazy to normal, how would you do it?
578. What is the most freaking mistake I made as a child?
Want to start a conversation but unsure how to go with it? These funny conversation starters will help you when you want to break the ice while sharing a laugh.
579. What was the wildest challenge you ever accepted?
580. Tell me about your most embarrassing talent.
581. Can you describe yourself with app names?
582. Did you ever lie about yourself to impress someone?
583. Are you more likely to die by starving or by overeating?
584. Who is your embarrassing crush?
585. Did you ever bunk your school?
586. Are you a cool person or a cute one?
587. Who makes disgusting food but you never told them out of politeness?
588. If you meet some creepy looking stranger in the elevator and s/he starts a conversation with you, would you respond or ignore?
589. What is the biggest cultural shock you ever faced?
590. What was your best high school prank?
591. If your happiness makes your enemy happy, are they still your enemy?
592. If you had to survive at a mental asylum, would you pretend to be insane to fit in?
593. Did you ever fart and blame it on someone else?
594. Would you like to be a part of your crush’s life as a side character or would you prefer not being there at all?
595. Have you ever cursed someone knowing they couldn’t understand or hear what you are saying?
596. Which seemingly cute looking creature do you find creepy?
597. If someday your doppelganger appears, how would you prove that you are the real one?
Great Questions for a Good Laugh
No need to think a lot when all you want is some fun and laughter. These great questions can do the job for you!
598. What is the one 100% effective tip to get dumped on the first date?
599. Tell me one superstition you believe in though you know it is a superstition.
600. What is your one politically incorrect opinion you would like to share?
601. Would an anteater die if it eats anything other than ants?
602. Can you make me jealous?
603. What sounds sexier – horns or tail?
604. Do you think it would be good if there were rabbits on the moon?
605. What were the most gibberish lyrics you were ever singing all day until you found the real one?
606. If you could change the color of your body like a chameleon, how would you use the ability?
607. Poor and pretty or rich and ugly – what do you want your crush to see you as?
608. Do you change your way of speaking if you visit a high-profile place?
609. What one funny smell is addictive?
610. Do you think you can love someone without ever seeing them?
611. Suppose you want to kill someone. Where would you take them to do so?
612. If you could appoint anyone in the world as your bodyguard, whom would you choose?
613. What seems like your soul food? One that fits your personality.
614. How great a fraud you can be if you want?
615. Can you make us dislike you by telling us one of your hobbies?
616. What normal body function seems totally abnormal?
617. Do you think you would be embarrassed if your pet starts talking about you?
618. What one thing you can say to make people paranoid about you?
Good Questions to Make Mood Light
When things are dull, some light-hearted funny questions are key to a better mood. You can simply ask these to make the situation light and entertaining. Here are some great mood-lifter questions –
619. Being naked in front of someone or letting them see everything in your mind ever – which would you choose?
620. What was the last weirdest thing you have in your browsing history?
621. Did someone ever walk in on you while you were crazily dancing or posing in front of a mirror?
622. Have you ever stuck a chewing gum under a table?
623. When was the last time you pretended as a fool just to avoid other fools?
624. Do you ever pee in a pool?
625. Have you ever had imaginary interview sessions in the shower?
626. Do you kiss with eyes open or closed?
627. What have you ever done to look sexy but ended up looking weird?
628. Have you ever sleep-talked?
629. What is the taste of sweat? And how do you know this confidently?
630. Do you think you’d say yes if your favorite celebrity would propose to you?
631. Have you ever been caught cheating in an exam?
632. Did you ever catch someone checking your belongings?
633. What kind of people can make you nervous just by looking at you?
634. Did you ever throw on a jacket on something too weird and go to a party playing all cool?
635. What is your favorite excuse to avoid outings?
636. Do you have any pictures of you in weird poses that you don’t want to show anyone?
637. If you had to invent a completely different ice cream flavor, what would it be?
638. Name a smell for each person present here that describes their personalities well.
Flirty Questions to Ask a Guy or Girl
So, you’re having a fun time with your crush! Then what can be better than making the questions funny plus flirty? And who knows, this is the chance you were looking for all along. So, do give it a try! Just make sure they’re comfortable.
639. Can you tell what makes you nervous when interacting with someone of the opposite gender?
640. What is the perfect atmosphere to set up your mood for a kiss?
641. Can you tell your favorite kind of foreplay?
642. What is the sexiest outfit you wear to bed?
643. Can you share your most romantic fantasy?
644. What are some simple things you find cute when a person does it for you?
645. If I flirt with you, would you enjoy it?
646. What one thing I can do to make you fall for me?
647. Tell a little gesture or thing about a person that can excite you romantically.
648. What is the first thing you notice in a person on a date?
649. If you had to seduce me now, how would you do it?
650. What kind of massages do you enjoy most?
651. Are you a person who can easily get jealous?
652. What is the best spot for you to be kissed?
653. Can you share your secret romantic fantasy?
654. What makes someone hot?
655. If you can add one thing to your sex life, what would it be?
656. What is the most sexual spot of all your body parts?
657. Tell one pick up line that is a cliche in tv shows or movies yet you like it.
658. What chances are there of you falling in love with me? So, would you like to try?
659. When was the last time you felt butterflies?
Funny Personal Questions to Ask
When your conversation is picking up, you can make it more intimate with some well-knit questions. Here’s a list of some funny personal questions to ask a guy or girl. Let’s explore!
660. What is the most similar smell with which you can compare your body odour?
661. Did you ever do something that proved you are an idiot?
662. How do you groom your underarms?
663. What is the worst situation you were in when someone walked in?
664. Give an example of how high maintenance are you?
665. Are you a bathroom singer or dancer?
666. When was your first time? How was it?
667. Can you tell the most embarrassing thing you ever did in front of your parents?
668. What is the one thing you did for money that is a bit weird or embarrassing to admit?
669. Do you pee in a shower?
670. What is a misconception people have about you that you secretly enjoy?
671. Can you tell what is your weirdest food habit?
672. Share an incident when you were really mean.
673. What is the strangest place where you have a birthmark or a mole on your body?
674. Can you share the most embarrassing thing you ever did on a date?
675. Where are you crazily ticklish?
676. Have you ever stolen something?
677. Who is your first love?
678. Do you snore or grind your teeth in sleep?
679. How do you look when you wake up? Describe it in 3 adjectives.
680. What is the weirdest designed undergarment you own?
681. Can you tell your weirdest fear?
682. When was the last time you got dumped by someone? Can you share the reason behind it?
683. Have you ever been to jail or detention? For what?
Funny Truth & Dare Questions
The classic truth or dare game is perfect when you need some fun and spice added. Plus, you can ask those questions that you won’t be able to otherwise. So, take some hints here –
684. Can you show your browsing history without deleting it?
685. Have you ever dropped your drink on your shirt in a professional meeting? Can you show how you reacted?
686. Did you ever crave for something inedible? What was it? Did you eat it?
687. What is the craziest thing have you ever done in an elevator? Or, what was your craziest experience in an elevator?
688. Did you ever pee in a public bath or swimming pool?
689. Have you ever walked into someone’s room while they were doing something embarrassing?
690. Do you give imaginary Oscar-winning speeches or something in the shower?
691. If you had a signature dance move, what would it be? Can you show it?
692. Did you ever farted in public and then pretended that you have not done it?
693. Have you ever burped in the middle of a kiss?
694. If you get to know that your best friend is having an affair, who is the first person that comes to your mind with whom your friend can have an affair?
695. Can you do a bell dance now as your life depends upon it?
696. What would you do if you and your friend had a crush on the same person?
697. Can you tell what was the last lie you told?
698. What are the things you think about while in the toilet?
699. Name one thing which you pretended to like in a situation just to look cool.
700. Rate yourself as in how good a kisser you are. Can you prove it?
Funny Questions to Ask – Final Words
Since we’ve got some amazing funny questions to make things great in every situation, let’s not waste another minute. Enjoy having a fun conversation with everyone in every situation. And don’t forget to laugh!
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That one person in the room who is always with a book and gets excited when it's time for some small-deep conversations - that's Kirtika. She loves words, Arts, Psychology, and everything that asks for her creative self. If you smiled more, even a bit, after coming here at ThePleasantConversation, chances are high, she'd be glad!