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Questions to Ask in Any Situation – the List of 700

Questions to Ask in Any Situation – the List of 700

Updated on May 17, 2022 | Published on November 17, 2021
Reviewed by Katina Tarver, MA (Mental Health and Wellness Counseling), Life & Relationship Coach
Questions to Ask in Any Situation - The List of 700 Questions

With some people, you just click. Yes, you start a great talk with them effortlessly. While there are others with whom the conversation always lands south.

But the good thing is – with the right bunch of questions to ask, you can make any conversation better. 

So while you might never become friends with your neighbor or that cousins’ cousin, you can make your talk less weird, more pleasant. As well there might be some with whom you’d click with every question in this list! 

The key is – asking great questions effectively. Let’s see how – 

Questions to Ask in Any Situation - the List of 700
Questions to Ask in Any Situation – the List of 700

Questions to Ask 

First thing first. Why questions at all? Because small talk or deep one – we want it to be a real talk.

Yes, not the random passage of information with not-needed pauses, nervous gaze, or alternative monologues. And questions are a great device for it. In brief, questions are powerful

Often answering questions lets people open up more easily. So the conversations are more meaningful. Also, it lets you share your perspective effortlessly.

Often when you are clueless about how to proceed, questions let you steer the talk in the right direction. 

In other words, when you ask a question, you open a box of thoughts. People add their perspective to it. And the conversation blooms with new ideas, visions, and obviously new scopes of fun.

Now, are you up for a great conversation? Here’s a list of 700 well-curated questions. So you’re never going to run out of questions to ask in any situation. Let’s dive deeper.

Good Questions to Ask to Get to Know Someone

Want to get to know that cute stranger? Are you looking for some icebreaker questions to escape the awkward pause?

Or, maybe you just want to understand a person better. Whatever is your situation, these questions will surely come in handy to you – 

1. How would you introduce yourself without telling your profession? 

2. Are you good at telling people what you want? 

3. Do you have many friends or fewer? How close are you to them?

4. What one piece of advice would you give someone for living a good life?

5. If you could keep one thing constant for the rest of your life, what would it be?

6. How do you usually like to pass the time in your leisure?

7. Do you like big parties or small meetups?

8. What are you proud of in your life? 

9. Are you a social butterfly? Or, are you simply the opposite of it? 

10. Do you think you can make people happy? 

11. How difficult is it for you to say no to someone? Rate it on a scale of 1-10. 

12. Are you generally considerate about others’ opinions? Or, do you not care what people think about you?  

13. What is your favorite pastime? 

14. Do you often overshare and regret it later? 

15. What is the last thing you bought for yourself? 

16. Do you think you cherish yourself enough? 

17. What one thing is common in most of your friends? 

18. If you could, what one thing would you like to change about yourself? Remember, it should be about you, not your situation. 

19. Do you like the idea of being an overachiever? What is the one disadvantage of being one? 

20. Do you believe in yourself? How much on a scale of 1-10?

Questions to Ask People to Get to Know Them Professionally

Unsure how to break the ice in a professional setting? Like, all you can think about is their name and so on.

Go for these professional questions to get to know someone that make your conversation more useful and appropriate for the situation – 

21. What are your areas of interest professionally?

22. Are you more of a spontaneous worker or do you prefer setting schedules and deadlines? 

23. Do you prefer working alone or are you more of a team player? 

24. What was your best career decision ever? And why?

25. What was the most difficult decision you have ever made?

26. Can you share your biggest pet peeves about your job? 

27. Are you good at learning new things? 

28. What do you like most about your work life?

29. Do you like planning things? Or do you go with the flow? 

30. When are you usually most productive? 

31. Are you happy with your current job? 

32. What made you proud of yourself recently? 

33. If you had to give one piece of advice to someone, what would it be?

34. How good are you at the leadership position? 

35. What made you choose your current profession? Do you still feel the same about it?

36. What was your first job? Can you share your experience with it?

37. Where do you see yourself professionally in the next 10 years? 

38. Have you ever made a wrong decision in your professional life? 

39. Did you ever have a mentor? Also, would you like to be a mentor for someone else?

40. What is your dream career? How close are you to it? 

Questions to Ask Your Boyfriend

Your man deserves more than a random gift or your daily this and that. He deserves your attention, some good laugh, and a conversation to open up. Makes sense, right?

Here’s a dose of funny, cute, deep, romantic questions to ask your boyfriend –

41. Have I told you before how handsome you look to me? 

42. Where do you see yourself in the next 10 years? 

43. Is there something you always wanted to do with me? 

44. Do you want me to kiss you or cuddle you? 

45. What are your favorite memories with me? 

46. Do you think we’ll be able to carry a long-distance relationship well? 

47. What relationship questions do you think we should ask each other?

48. Would you like to have children in the future? 

49.  What is the craziest thing you’ve ever done in an unexpected situation? 

50. Can you tell me one thing that you like about me? 

51. What is your most romantic fantasy about? 

52. How do you like being pampered by me? 

53. What is your favorite smell?

54. Do you ever feel uncomfortable around me? 

55. What is your one crazy dream? 

56. Do I do something that makes you mad? 

57. What is the funniest thing you’ve ever done? 

58. Can you guess what made me fall for you? 

59. When did you start having feelings for me? Can you guess the same about me? 

60. What does your perfect day look like? 

Questions to Ask Your Girlfriend

Do you want to bond better with your girl? In a way that lets her share her random thoughts, crazy ideas, or romantic moments effortlessly?

Well, your answer lies in these cute questions to ask your girlfriend. Here we go.

61. How do you want me to show my love? 

62. Do you want me to hug you? 

63. What is your ultimate deal-breaker in a relationship? 

64. Do you feel loved enough? What can I do to make it more for you? 

65. How do you like spending time with me? 

66. Do I know your close friends? So what can I do to be on their good side? 

67. What do you think about getting married?  

68. Can you share what made you fall for me? 

69. What do you like most about me? 

70. How competitive are you in guarding your boyfriend? 

71. What color do you want me to wear in bed? 

72. Do you want to dominate in bed? 

73. Where do you see us in the future? 

74. Do you like surprise dates or planned ones? 

75. What is your dream life like? 

76. How were you at 17? And how do you want to be at 70?

77. What proofs you’re completely crazy? 

78. If you were granted any wish, what would you ask for? 

79. What do you love about yourself? Can you guess what I like about you? 

80. What makes you happy? 

Questions to Ask Your Crush

Finally, you got a chance to be with your crush. Things seem good. The only thing is you don’t know what to say. If that’s you, calm down! You can bond with them over an interesting talk.

The key is – let them feel good and be honest with themselves. Here are some questions that help you connect to them while expressing your feelings subtly. 

81. How can I make you smile? 

82. What sounds like fun to you? Can we give it a try together?

83. Do you want to try something new now? Like, do you have something in mind?

84. What is your favorite way to spend a day? 

85. Do you believe in love at first sight? Why or why not? 

86. How would you react if I ask you for a date night? 

87. What can I do now to put a smile on your face?

88. Do you like to pick up lines? Well, so that I can pick a good one for you.

89. Would you like to go on a casual date with me someday? 

90. Romantic relationships of which fictional characters make you swoon? 

91. What do you think about the idea of online dating? 

92. Do you have any hobbies? What is it? 

93. What makes you fall for someone? 

94. How good are you at guessing who has a crush on you? Do you think someone around feels so about you? 

95. What is the coolest thing you have seen someone do? 

96. Have you ever had a secret crush on someone? So, what did you do about it? 

97. What kind of love confessions do you like? 

98. Are you willing to be with someone? Okay, how about me?

99. Would you like to go on a long drive someday? 

100. On a scale of 1-10, how hopeless romantic are you? 

Good Questions to Ask

Often we don’t know what exactly the situation is. Like, something is going on, you need to talk, but about what?

If you’re stuck in one such situation, these open-ended questions are here for your rescue. These are great for small talks as well as deeper ones. Still, unsure? Give it a try!

101. What are you grateful for? 

102. Did you make someone laugh recently? Can you share the memory of when you last made someone smile? 

103. What are your most annoying childhood memories? 

104. Have you ever regretted watching a movie completely? And why?

105. Which web series did you binge watch recently? 

106. Can you recommend some great tv shows? 

107. If you have to live the rest of your life on a deserted island with any people you want, whom would you choose to be with you? 

108. What do you like and dislike about having an extended family? 

109. Have you ever got a wise word from someone that made you say – ‘This is the best advice I’ve ever received?

110. What weekend plan seems like a good idea to you?

111. How would you describe your perfect day? 

112. Which inanimate object would you like to turn into if you had to choose one? 

113. Do you know someone who seemed rude or something but turned out to be a completely different person?

114. Have you ever mistaken someone for someone else? What was it about? 

115. How easily do you get embarrassed? Can you give any examples? 

116. Who is the first person to come to your mind when you’re in any trouble? 

117. Do you like cringe stuff secretly? 

118. What made you excited recently?

119. Can you show your favorite dance move? 

120. What makes you a good company? 

Great Questions to Ask

Conversations aren’t great themselves. It’s the questions that make them great. These help people express themselves and let them understand each other better.

Ask these questions when you want to have a conversation that is something more than usual.

121. If you could rewind your life, where would you go? 

122. What one thing annoys you most about your favorite person? 

123. Do you think you are more naive or coyer? 

124. What is your ultimate trick for breaking the ice with an attractive stranger? 

125. Can you share your favorite childhood memory? 

126. Which tv show did you start thoughtlessly but it turned out unexpectedly amazing? 

127. Did you eat something too delicious recently? 

128. What was your favorite subject in high school? 

129. If you had to turn everything’s color into one, which one color would it be? 

130. What is your favorite holiday idea? 

131. Can you whistle better or wink?  

132. Who is the first person coming to your mind when thinking about having a lot of fun?

133. Do you think you have found the purpose of human life?

134. Are you an obedient person or do you have more of a rebellion?

135. Who is the meanest person you have ever met? 

136. Have you ever felt so wrong that you couldn’t even protest? 

137. What one thing would you change about your least favorite person if you could? 

138. Do you believe in ghosts? Why or why not? 

139. Do you think everything in the world has a reason? 

140. Would you talk to a beautiful stranger who approaches you out of blue?  

Best Questions to Ask for a Late Night Conversation

Some questions are like the beauty of a peaceful night. When the chaos calms down, you get a chance to peek into your heart.

These questions are best when I want to connect to someone on another level. It’d be a different experience altogether. 

141. Have you ever accepted a challenge for fun but things got serious later? 

142. What one thing do you do on your part to improve the world?

143. Is there someone you want to talk to now but somehow you wouldn’t? 

144. What frustrated you recently?

145. Are you true to your heart mostly? 

146. What is something in which you are uselessly great? 

147. Can you describe everything in your mind in five words? 

148. What is the funniest joke you can tell me to make me laugh out loud? 

149. Death of which fictional character disappoints you even now? 

150. If you could go into fiction, what would it be about? 

151. What is the last thing on your bucket list? 

152. Did something or someone disappoints you recently? 

153. Are you more practical or more dreamer? 

154. Which music did you listen to last? 

155. If you could learn one weird thing, what would it be? 

156. What takes most of your attention while listening to a song – lyrics or music? 

157. Have you ever done something extremely unpredictable? What was it about? 

158. Can you tell one lie that we would believe to be true? 

159. Did you ever fail any paper in high school? 

160. Would you prefer to be an intelligent-looking fool or a fool looking intelligent? 

Easy Questions to Ask

Okay, you don’t want those complicated sophisticated questions. You want a talk that is easy-flowing and good to go.

That’s great when you want a quick dose for small talks and fun banters. Plus, these are entertaining enough to not let your talk bland. Here we go – 

161. What is the meaning of your name? 

162. Do you prefer junk food or healthy meals? 

163. Are you a rule-following or a rule-breaking person? 

164. What delicious thing you had recently? 

165. How good are you at making cute faces? Can you prove it now?

166. If any of your simple skills could be a sport in the Olympics, what would it be? 

167. What is the funniest thing you’ve heard a child saying? 

168. Children or adults – who is ruder? 

169. What one thing did you read as a child but still can’t understand well? 

170. How would you greet the president if he meets you randomly on the street? 

171. What do you like more – sweet or spicy? 

172. If you had to choose one most awful food ever, what would it be? 

173. Who is your celebrity crush? 

174. Is there something that can make you happy almost always? 

175. What is the weirdest dream you have ever had? 

176. Arts or sports – how would you like to spend your leisure? 

177. Have you ever drunk-called someone? 

178. Would you like to learn a new language? Which one? 

179. Are you a foodie? Okay, what is your favorite food? 

180. What is the best luxury you can think about? 

This or That Questions to Ask People

Choice questions are almost always a great treat to your conversation. These are quick, playful, and often serve as great prompts for fun small talk.

Bonus, what makes it even better is – these questions are good for a large gathering too. Let’s explore!

181. Would you rather dance on the street or sing on the highway? 

182. Ketchup on cake or candy on hot dogs – what would you choose? 

183. What sounds more entertaining – movie or tv shows? But web series won’t count. 

184. Would you open a bookstore in the hills or a restaurant in the city? 

185. Direct confession or hitting on you allusively – how would you prefer it?

186. Would you rather babysit an adult or have a serious debate with a kid? 

187. Beer or wine – what sounds better? 

188. Summers or snow – which is best for a cozy day? 

189. Would you always overshare and regret or under express and regret? Okay, not regret maybe? 

190. Would you rather take your friends to a family function or your family to a friends’ party? Umm.

191. What sounds more romantic – long video calls or writing love letters? 

192. Messy unmanageable hair or no hair at all – what would you choose? 

193. Would you rather fight to prove your point or avoid arguing by falsely accepting your mistake? 

194. Happy endings and sad beginnings or vice versa – what is more interesting?

195. Would you rather be overconfident or always undercount your skills?

196. Expensive sophisticated gifts or simple handmade ones – what would touch your heart more? 

197. Would you rather have a pet or a baby? 

198. If humans could have only one, what would it be – ears or nose? 

199. Would you rather wash dishes or clean the bathroom? ‘None’ won’t do. 

200. Would you rather pluck a flower or plant one? 

Hypothetical Questions to Ask Someone

Be it any conversation, hypothetical questions are almost a must. Reason? These are super fun and great to go.

Besides, these open doors for imagination and some out-of-the-box perspectives. So, when the mood seems right, don’t forget to try these out –

201. If you could erase one historical figure from history, whom would you choose? 

202. Suppose you had the power to listen to someone’s inner talk. But you had to compulsorily share this secret with any one person. Whom would you choose? 

203. If you could decide how your emotions work, would you ever intentionally fall for someone? 

204. Would you like to write fantasy novels if all of your stories turn into reality? 

205. If you could control who doesn’t love you but not the other way around, how would you choose power?

206. Suppose you get the power to make one thing socially acceptable that isn’t now. What would you choose? 

207. Suppose you meet your doppelganger one day who seems to live your dream life. They offer you to exchange your life. Will you do that? 

208. If you have only 12 hours to live, how would you spend your time? 

209. Suppose you won the lottery of a billion dollars but you had to give up something very precious to you in return. Would you still take it? 

210. If you could get wings in exchange for any part of your body, what would it be? 

211. Suppose you could date any fictional character in real life. Whom would you choose? 

212. If starting today, no one could ever lie, would you like it? Why or why not?

213. If you had the power of permanently changing your whole personality just as your crush likes, would you do that? 

214. Suppose some content is created about your life on a dark web and then everything happens the same as it. After knowing about it, would you search for it to find out the person behind it or would you rather leave it to ensure your safety?

215. If you could erase all your embarrassing memories from everyone’s mind, would you do it? 

216. Suppose you could make everyone in the world forget any part of history. What would you choose?

217. Would you rather live a simple life with love or a luxurious life without love? 

218. If you could steal any one thing from anyone, what would it be?

219. Would you like to know a useless truth if it made you sad or would you like to believe the lie that made you happy? 

220. Suppose you start a conspiracy theory and it turns out to be true. What is it most likely to be? 

Basic Questions to Ask

A bit nervous to start a conversation? Let’s go with the basics. These are safe, okay to begin with, and good to bond over slowly. Also, you get to learn more about someone without seeming nosy. Let’s dive deeper here – 

221. What do you do for a living? 

222. Do you like watching movies or reading books? So, would you suggest something good to me? 

223. What is your one all-time comfort food? 

224. Do you prefer short talks or deep ones? 

225. What is the coolest place on top of your travel list? 

226. Do you have any hidden hobbies that you would like to talk about? 

227. Are you into any outdoor activities? If yes, what are they?

228. Do you prefer an action-packed vacation or a laid-back one? 

229. What do you like to do most in your free time?

230. Are you planning to learn something new recently? Or, do you want to but haven’t planned yet?

231. How do you prefer spending your self-time? 

232. Would you rather go to a party or read books at home? 

233. Okay, who is your favorite celebrity?

234. What is your favorite song? Do you like music? 

235. What was your favorite subject in school?

236. Do you like a peaceful day or an adventurous one?

237. Can you tell me a joke that made you laugh recently? 

238. What is the best way to be friends with you?

239. Are you good with the latest technology?

240. Do you prefer a stable job or business? 

Simple Questions to Ask

When you are confused, simplicity is usually the best answer. You want to make things meaningful but not lead to deeper existential thoughts.

Well, it makes sense. These simple questions to ask someone are great for a chill conversation.

241. Do you prefer tea or coffee? 

242. What is the last book you read? How do you like it? 

243. Do you like working out? So, do you have any workout routine or something? 

244. What one unique career would you like to try if you get a chance? 

245. If money was no object, how would you like to live your life? 

246. What ice cream flavor describes your current mood best?

247. Do you make wishlists? What is the first thing in it, if yes? 

248. How do you like to spend time with your family members?

249. What is the funniest gift you’ve ever received? 

250. Is there something that a lot of people like but you don’t? 

251. What compliment made you blush or laugh out loud? 

252. How much time do you spend on your phone?

253. What home chorus do you enjoy? Yes, enjoy. 

254. Do you like adventure? What is the last adrenaline-spiking thing you did? 

255. Which place would you like to visit at least once in your lifetime? 

256. Are you a morning person? Or do you rule the night? 

257. What is the cutest nice name you have ever got? And the most annoying one? 

258. Have you ever talked to someone from a very different culture, background, or life as yours? So, how was it? 

259. Do you sing in the bathroom? Or, do you dance? 

260. If you could work for any famous person, who would they be? 

Funny Questions to Ask

The popular recipe for being the star of any conversation is a great sense of humor. And when you add a bit of humor with some entertaining questions, your banter is bound to wouk.

Plus, a bit of laughter can make these questions go well as fun conversation starters too. Here we go!

261. Do you feel awkward talking to someone after a long time? 

262. What is the funniest smell you know? You read it right. 

263. What is the craziest thing someone did to you on a date? Have you ever done any such thing? 

264. Why do you love the stupidest person in your life? Don’t tell me, it is you. 

265. What is the weirdest thing you have ever tasted? 

266. Have you ever fiercely argued for the wrong side? Was it intentional or unintentional? 

267. Have you ever made a fool out of you? So, what’s the story? 

268. What is the most exaggerated thing you have ever read, heard, or seen? Remember, most exaggerated. 

269. Do you have something useless that you protect like your life? Well, mostly we have one! 

270. Do you make weird faces when no one is around? Can you demonstrate your skills now? 

271. In what weird position has anyone caught you ever?

272. Have you ever thought of something so crazy in an ongoing meeting that made you burst into laughter? 

273. Who is the sexiest animal? And why so?

274. If someone blackmails you to share your browsing history publicly, how would you react? And how would you negotiate? 

275. What is the craziest way you can think about to scare everyone on the street? 

276. Have you ever been caught by someone in a weird position with your friend? 

277. If you had to make one crazy outfit compulsory for everyone in your company, what would it be? 

278. Have you ever visited dressed crazily in a theme party that wasn’t actually a theme party? 

279. What one thing you casually do that would make Satan your fan? 

280. Do you have any crazy ideas to start a cult? Are you implementing it secretly? 

Deep Questions to Ask

On some random days, we all crave something deeper. A talk that is not just like a formality but an invitation to inner expression.

So, are you too looking for some deep questions to ask a girl or guy? These prompts are perfect for a deep conversation. 

281. Do you love yourself enough? 

282. When did you cry last time? Can you share why?

283. What motivates you to be alive? It can be anything. 

284. Do you think we really have a purpose in life? Why or why not? 

285. Can absolute happiness be real? Why do you think so? 

286. How much do you know yourself? So, have you ever done something so unpredictable that it even surprised you?   

287. What little moments would you like to preserve in your memories always?

288. Do you think death is cruel? Or, is it an escape from the cruelty of the world? 

289. Are you missing someone? 

290. What is your most spontaneous decision ever? 

291. Do you believe in true love? 

292. Is there someone who makes you believe in humanity? 

293. Do you think you’ll be happy after getting all your goals achieved? 

294. Have you ever prayed for something? 

295. Do you want God to be true? It’s not about your belief but your want.

296. How often do you fake your laugh? Why do you think you do so? 

297. Do you think there might be someone perfect for you somewhere in the world whom you would never meet? 

298. Have you ever experienced true freedom? Why do you think so? 

299. Do you think you are deceiving yourself in any way? 

300. For a moment, would you like to forget your existence and just be a part of the cosmos? Just for a moment.

Questions to Ask Your Friends

Usually, we don’t need to think twice before talking to our friends. But sometimes, your questions might feel bland.

Or, maybe, it is not helpful in knowing them better. If that’s the reason you are here, these questions to ask your friend would be more than helpful. Check these out –

301. Have you ever met someone who has a lot in common with you?

302. What one myth do you desperately want to be real?

303. Do you feel comfortable around new people? How comfortable are you with me? 

304. What red flags do you always notice before committing to a relationship? 

305. Are you a coffee person or a beer person? 

306. Do you like gossiping with me? 

307. If you could skip any one thing necessary for a professional setup, what would it be?

308. Have you ever tried flirting with me but I didn’t get it? 

309. Do you have any good memories of us together that you’d like to share? 

310. What makes you my favorite? 

311. Do you have any weird hobbies that I’m unaware of? 

312. Can you guess the first impression I had of you? What was your first impression of me? 

313. If we had to start a failed business together, what would it be about? 

314. Have you ever had a crush on someone that you are embarrassed to accept now? 

315. If you could have any superpower, what would it be? How would you use it? 

316. If you were famous, what do you think it would be about?

317. What is your best birthday ever? And what makes it so special? 

318. What is your all-time favorite excuse to cancel a plan? 

319. Have you ever thought about running away from your house as a child? 

320. If you could ask me any favor, what would you ask for? 

Interesting Questions to Ask

Questions that make you engaging and fun? So, you are up for some interesting questions to ask a girl or guy. These are not bland yet not too outlandish.

Just the perfect dose to pull off any conversation like a pro. Here we go –

321. What things do you do that are ‘not for your age’?

322. Do you have any childhood secrets that you want to share now? 

323. Which topics sound like all-time great conversations to you? 

324. How good are you at the art of negotiating? 

325. What matters more – EQ it IQ?

326. Is there any movie that you have practically memorized? 

327. Do you have any regrets? How do you think you can move on? 

328. Who is the most impressive person you have ever met? And what makes them impressive? 

329. Which childhood book do you think is more apt for adults? And why so?

330. What is your idea of making it big in life? 

331. Have you ever been cheated by someone? 

332. Do you think humans are innately evil? Why or why not? 

333. In the coming years, what do you think you would miss most about your present life? 

334. Do you think Science is more important than Arts? Why or why not? 

335. How would you describe yourself in one word? 

336. What one simple thing are you almost addicted to? 

337. If you could have anyone wish granted, what would it be? 

338. Do you believe in God? Why or why not? 

339. If you could get rid of any one of your emotions, what would it be? 

340. Can you ever do something completely selflessly? 

Weird Questions to Ask

Make them giggle. Let the conversation go insane. And show off your wacky side unapologetically. How? Well, these amazing weird questions make every conversation weirdly engaging. So, are you up? Yep!

341. Would you rather pet a dinosaur or fight a lizard? 

342. Suppose you are stranded at a hotel in the rain and storm. The only room available has a rumor of being haunted. Would you still take it?

343. Have you ever tasted something inedible and found it good? 

344. If someone tries to kill themselves, should they be charged with attempted murder (self-murder)?

345. How would you react if you met an alien on the street? 

346. If you fell in love with a paranormal creature and they wanted you to become one, would you be? 

347. Have you ever passed on a gift to someone else? What was it? 

348. Why do we want more hair on the head than other body parts? Like, hair is hair.

349. What do you want to change in the year 2050? 

350. Have you felt that your intuitions work? Okay, when? 

351. Why do people often open their mouths while applying eye makeup on themselves? 

352. What is the one sign that proves that you are you and not a humbug doppelganger? 

353. How would you begin your TED talk? 

354. Do you think the person who created the rules of English spellings was high? 

355. What can I do to make you jealous?

356. Are there any useless things that you do all the time? 

357. Do you think an animal can commit suicide? 

358. If you had to rename yourself, what would you choose? 

359. Would you rather spend a day with an annoying unwanted guest or work overtime? 

360. If one day your family finds that you are jailed, what do you think their first guess would be? 

Dirty Questions to Ask

Fun dirty questions are great for a good time together. But not great until you’re sure that the other person is liking it.

So, it’s always advisable to proceed with the first question below so that things don’t get weird or unwanted. If the answer to this question is a yes, then both of you can have some fun.

361. Would you like to talk dirty now? So, can I proceed? 

362. Which is the best place to have sex according to you? 

363. Do you have any fetishes? And what are they?

364. What sex position comes to your mind first if asked now?

365. Suppose the person you’re talking to asks you for something intimate. Would you reciprocate? 

366. Which of your body parts is most kissable? 

367. Can you tell me the most insane sexual experience you have ever had? 

368. What color underwear suits you most? 

369. Do you have any specific type? Have you ever had someone like that? 

370. Do you like making noises in bed? 

371. What do you wear to bed usually?

372. Touching at which part of your body excites you most? 

373. When were you most excited about seeing me? 

374. Have you ever had sex with someone very unexpectedly? 

375. Do you like one-night stands or do you prefer commitments? 

376. What are your favorite sex toys? Do you want to shop for these together? 

377. Would you like to read a sexy story with me? 

378. Dirty texts or dirty talk – what sounds better? 

379. What type of foreplay do you like most? Do you want to try? 

380. What is the most erotic movie you have ever watched? 

Flirty Questions to Ask a Girl

Who doesn’t like boasting their flirty skills? So, if you’re here for the same, we’ve got you.

These flirty fun questions to ask your girlfriend, a friend, or say, anyone, is the gospel. Just be yourself. Be confident. And enjoy the conversation. 

381. What is the best way to ask you for a kiss? 

382. Do you want to recreate your favorite romantic scene with me? 

383. What do you think singles miss most?

384. How can you be this charming? I almost felt butterflies in me? 

385. Are you good at taking hints when someone is hitting on you? Did you take the hint then? 

386. How can I make you blush? 

387. Would you like to go on a date with me? 

388. How do you want your man to show his love to you? 

389. What is the first thing you noticed in me? Do you usually notice it in every man you meet?

390. What first thing attracts you to someone? 

391. How easily do you get jealous? 

392. Are you open to new love applications? How can I apply? 

393. What is the first thing on your bucket list? Do you want a companion to fulfill it? 

394. Can you guess what I want to do right now? 

395. How can I get close to you? Can I have any VIP pass or something to enter your heart? 

396. Do you want me to hug you? 

397. What is the simplest way to make you fall for me? I should know my assignment well. 

398. I never knew I could flirt before meeting you. Won’t you have a congratulatory dinner with me? 

399. Are you on any dating app? Would you swipe me if you find me there?

400. How would you like to spend a cozy winter night with me? 

Flirty Questions to Ask a Guy

Want to start a flirty banter with that guy? Okay, why not! Boost your confident self and flirting skills while bringing a smile to his face.

These fun questions are cute, romantic, and good for some laughs together. Check these out –

401. Would you like it if I held your hands? 

402. Are you always this cute? Or, is it my presence by any chance? 

403. Do you believe in destiny? Like, we might share a destiny. 

404. How likely is it for you to fall for me? 

405. Would you like to watch a movie with me? Or, would you play video games with me overnight? 

406. What sounds like a perfect date for you? I need to prepare for it accordingly. 

407. Do you want to see butterflies? 

408. So, do you believe in love at first sight? I think I’ve started believing in it? 

409. Would it embarrass you if I tell you how much I like you?

410. Can you guess what’s in my mind? 

411. How can you always look this inviting? Is there a secret? 

412. Can you beat me in an eye contact game? We need to look into each other’s eyes without blinking. 

413. Are you ready to feel butterflies? 

414. Do you like being pampered? Can I do it for you? 

415. How would you like to spend the rest of your life with me? 

416. Is there something that you live to do but are embarrassed to admit in front of others? Promise, I won’t judge. 

417. Do you like cuddles? If you want, we can give it a try now. 

418. Do you believe in soul mates? Who knows you are with yours now? 

419. Do you like it if the other person makes the first move on you? Or, are you going to hit on me first? 

420. What is the first thing you noticed in me? 

Questions to Ask on a Date

On a date? A good conversation is much needed. While a fun flirty banter is great, some important questions about your compatibility are a great addition to your date conversation.

So here we have some cute, some flirty, and some meaningful questions to add in your lovely date. 

421. How do you want to spend our date? Is there anything I can do to make the day more special? 

422. Can you tell me some fun facts about you? 

423. What are you looking for in your partner? 

424. How do you usually spend your days? 

425. Do you prefer casual flings or long-term commitments? 

426. What is something that you never want to forget? And why? 

427. What is the last thing you did that made you happy? 

428. Can you recommend some great books or movies? 

429. If you could live anywhere in the world, where would it be? Or, what is your idea of a perfect place to be? 

430. How easily do you connect with others? 

431. What are some silly things you believe in? 

432. Do you have any special talent you want to talk about? 

433. What is your favorite time of the day? Like, mornings or evenings? 

434. Do you have any hobbies? What are they? 

435. Is there something you are absolutely passionate about? 

436. What food do you love? Should we try some today?

437. What topic always sounds interesting to talk to you about?

438. If you had to choose a perfect job, what would it be?

439. Do you prefer more self-time or are you a social butterfly? 

440. What do you want from a romantic relationship? 

Personal Questions to Ask

Sometimes we might need to get personal. Like, things are going in that way. Or, you want to go comfier in your mutual comfort zone.

Well, whatever it is, these personal questions are great at work. Without being offensive, they are personal and good to go – 

441. Have you ever fallen in love with someone? Who is it? 

442. How important is money for you? 

443. Do you think you are healthy enough? Why or why not? 

444. What one habit do you want to change desperately but your efforts are not working? 

445. Do you have any weird habits that often embarrass you?  What are they? 

446. Do you have any regrets? 

447. Who are the closest people in your life? 

448. Do you think you are doing your best in life? 

449. Have you ever cheated on someone? Or, have you ever been cheated? 

450. What annoys you most about your current life? 

451. Is there something that makes you despicable? 

452. How do you judge people? Like, do you think your prejudices work on deciding someone’s first impression? 

453. How lazy are you? Can you give some examples? 

454. Have you ever been caught in an embarrassing situation by someone? 

455. What makes you all greedy? 

456. Is there something petty that you own?  

457. Do you have any guilt? What are they?

458. Do you behave with people based on their appearance or social status? 

459. Have you ever ruined someone’s day intentionally? 

460. Who is your secret crush? 

Juicy Questions to Ask

A question that brings more to the table? Yes, please. We all love some juicy questions when done with bland talk. These are great to add spice and make things engaging.

Plus, you’ve got some variety here so it won’t be like reading a list but a natural conversation. Let’s see –

461. Whose social media profile did you stalk last? 

462. How many people have you kissed? 

463. Did you ever fart loudly in front of someone? 

464. Is there someone I know with whom you want to sleep?

465. Would you like to try crossdressing? 

466. Can you share your one dirty secret? 

467. When was the last time you broke your promise? 

468. Is there someone you want to be mean with secretly? 

469. How practical are you in life? 

470. What is the last thing in your browsing history? 

471. Money or love – honestly, what matters more for you? 

472. Have you ever kissed someone publicly? 

473. Do you like it when someone hits on you? 

474. How would you like to be remembered after your death?

475. What one song is your all-time favorite? 

476. If you could be reborn as someone else, how do you want your life to be?  

477. Have you ever been punished publicly in high school? What was the reason? 

478. Have you ever lied to your parents? Why? 

479. Did you ever steal something? 

480. Have you ever tried to act cooler in front of someone? 

Questions to Ask Your Partner

A good conversation adds to your healthy relationship. It lets you share your thoughts, and understand each other better.

So, when you want to connect better to your partner, don’t forget to add these quality questions for couples. Grab two mugs of warm coffee and have a good time together. 

481. Are you happy with our relationship? 

482. Do you think we need to work on any part of our relationship?

483. What little thing did I do that made you happy?

484. Do you want to eat something delicious? 

485. How do you say you love me without saying it? 

486. Is there something adventurous in your mind that we can do together?

487. What one tip would you give me if we start dating again afresh? 

488. Is there something that annoys you about our relationship? 

489. Do you have any ideas to share our couple-time? 

490. Is there something that you wanted to share with me but somehow couldn’t?  

491. What are you looking for in the coming future? 

492. Do you have any special talent that even I don’t know about? 

493. What makes me sexy for you? 

494. Do you have any fantasies that you want to talk about? 

495. How was your day?

496. What is your proudest possession ever? 

497. Do you think we are spending quality time together lately? 

498. Who is your favorite celebrity crush? 

499. So, what is your favorite memory of us together? 

500. How do you want to age with me? 

Cute Dumb Questions to Ask

Dumb is cute. Cute is … well, we love it. So, why not try these cute dumb questions? These are great choices if you want some serious, on-point, meaningful talk.

But for a fun and good time together, it can be more than better. Won’t believe it? Try it yourself. 

501. Have you ever felt butterflies while holding someone’s hands?  

502. Do you think you are destined for someone? 

503. What makes you like your crush? 

504. How was your first kiss? Can you describe how you felt? Or, how do you want it to be? 

505. What is the cutest thing you have ever seen? 

506. Do all dogs go to heaven? 

507. What do you think makes you fall for someone? 

508. Forehead kisses or bedtime cuddles – what feels better?

509. Why are pigtails called pigtails? 

510. Candies or chocolates – what is more comforting?

511. Have you ever received love letters? So, how did you feel? 

512. Have you ever written love letters to someone? 

513. What makes babies so beautiful even though they don’t have teeth and hair? 

514. Is there someone with whom you just can’t stay angry no matter how hard you try? 

515. Do you think love songs really play in the background when you meet your love? 

516. Why do piggyback rides feel so cute? Should we try it?

517. How easily do you cry? 

518. Do you like watching cartoons? Which ones? 

519. Do you think angels exist? 

520. Are you a magician? Otherwise, how would you always feel magical to me? 

Truth Questions to Ask

In a game of truth and dare, you can make the mood. Right here you ask the question. And out the same repetitive boring one.

Don’t worry, you’ll not have to face this. With these interesting truth questions, you always have a chance to brighten up the mood and the conversation. 

521. What would you do if you became invisible? 

522. Have you ever done something mean to someone secretly? 

523. What is the cheesiest pickup line have you ever used? And did it work? 

524. What is your one dirty truth that you never shared with anyone? 

525. Have you ever lied about your relationship status? When and why? 

526. Is there something that you love to do but are embarrassed to admit in front of others? 

527. Have you ever got a clean zero in any paper? 

528. Who is your first love? Did they know this? 

529. Is there someone you secretly wish to give a tight slap on the face? 

530. Have you ever drunk-called your ex? 

531. How good are you at playing innocent? 

532. What is the weirdest food combination you like? 

533. Did you ever play dumb when someone was hitting on you? 

534. Have you ever flirted with your teacher? Or, say, did you have a crush on your teacher? 

535. What is something about your behavior that people often don’t believe you have? 

536. Have you ever flirted with your friends’ crush? 

537. On a scale of 1-10, what are your chances of being a sociopath? 

538. Have you ever done something illegal?

539. What do you love about yourself? 

540. Are you described better as a miser or a spendthrift? No middle ground is allowed. 

Questions to Ask Couples

Are you in a group chat or casual party with your couple of friends? So, confused, what to ask them? Well, these interesting questions to ask couples are here for help.

Besides, these are great to ask new couples when you want to make things easy and fun. Let’s explore more –

541. How did you fall for each other? 

542. What makes you the perfect couple? 

543. Did you ever plan a surprise for each other and get really surprised? 

544. Can you tell 5 good qualities about each other? 

545. What relationship tips would you like to give to other couples?

546. How similar are you to your partner? 

547. And how different are you to your partner? 

548. How much did you grow up as a couple? 

549. Do you think destiny decides relationships?

550. How do you manage conflicts in your relationship? 

551. Can you understand each other only through your eyes? 

552. How do you like to spend quality time with each other?

553. Are there any of the inner jokes that you’d like to tell us? 

554. Who usually apologizes first between you? Great, if both! 

555. What is your common favorite song? 

556. Do you have any funny memories with each other? 

557. Who proposed first in your relationship? How was it? 

558. Can you two guess each others’ moods by looking at your expressions? 

559. What is better being in a relationship than being single? 

560. Is there something that you miss about being single? 

Sexual Questions to Ask

Upo for raising the temperature of the room? Well, these hot sex questions would surely help you in making things fun, sensual, and hotter.

Give it a try. For a quick tip, ask them if they are up for some sexual talk before barging these questions unexpectedly. 

561. What do you think is most important to a healthy sexual life? 

562. Do you find the public display of affection comfortable?

563. How much emotional bonding matters for you in making a sexual relationship?

564. Do you prefer to do it with lights on or off? 

565. Is there something about sex you wish you knew before?

566. Can you tell some non-physical qualities that attract you to someone?

567. What is your biggest turn-on? 

568. Do you like the idea of a one-night stand? 

569. What are your secret sexual fantasies? 

570. How would you seduce someone? 

571. Would you like me to give you a full body massage? So may I?

572. What do you like more – making out rough or gentle?

573. Do you like including toys in bed? 

574. What do you think is the place to do it? Have you tried?

575. What are the things that enhance the mood?

576. Are there any outfits that you find very sensual? 

577. Do you get turned on with any smell? What is it, if yes?

578. How was your first time? 

579. Do you like making eye contact while making out? 

580. Is there anything that you specifically like to add in bed? 

Kinky Questions to Ask

So the mood is set. Your vibes are matching. And you are up for some not-so-boring kinky talk. Well, why not? After all, the more fun, the better.

So, here we go for some kinky questions that you can ask when you are looking for some pleasant fun time together. 

581. What is your one sexual fantasy that came true?

582. Do you like calling names to your partner in bed? 

583. What kind of porn do you like? 

584. Is there something that you watched in porn and would like to try? 

885. What is your guilty pleasure? 

586. Have you ever had a crush on a teacher? 

587. Would you like to have someone as a friend with benefits? 

588. Are you into roleplays?

589. What is your favorite position on the bed – dominating or submissive?

590. Have you ever tried a blindfold session? 

591. What do you think about a threesome? 

592. Have you ever tried existing? Do you think it’s fun?

593. Would you like to watch others in bed? 

594. Is your line being watched while you make out?

595. Do you have any position in your mind that you want to try?

596. What little thing turns you on in bed? 

597. Have you ever done it with a stranger? So, how was the experience?

598. Have you ever tried tying your partner or being tied up?

599. What is your unconventional sexual fantasy? 

600. Do you like having multiple sexual partners or one? 

Questions to Ask Your Ex

Breakups are common. So is facing your ex again. But a quick guide to talking to your ex isn’t that common. So it’s understandable if you’re feeling nervous, awkward, uncomfortable, or even annoyed.

Here are different questions that you can ask your ex depending upon the air between you two. 

601. Do you think our relationship was a mistake? 

602. If we would have never dated, do you think we would have been good friends? 

603. Why do you think we ended up like this? 

604. Is there anything that you are grateful about in our relationship? 

605. Did you ever consider me your best option? 

606. How do you think we should react when we meet each other? 

607. Can we move forward past our relationship? 

608. Would you like to keep a casual positive relationship between us? 

609. Is there something you wanted to tell me that you couldn’t till now?

610. How can we help each other move forward? 

611. Do you think we can get back together? What can we do about it? 

612. Is there something we could have done differently to save our relationship? 

613. What open ties do you want to close for a proper goodbye? 

614. Do you think our relationship deserves a second chance? 

615. Shouldn’t we just move on to our different paths? It’s okay if things don’t work.

616. Wouldn’t it be better if both of us maintain a distance for our better mental health? 

617. Do you think it’s the right time to forgive each other? 

618. Isn’t it okay if we don’t hate each other? Let’s just be there. 

619. What is the funniest thing about our relationship? 

620. Is there something left between us that we should complete? 

Freaky Questions to Ask

Looking for some freaky questions that catch people off guard? These freaky questions are cool, exciting, and fun at the same time.

Plus, the beauty is, they are not so predictable. So, your conversation will be engaging and unique. Let’s explore –

621. If someday you wake up and see yourself next to me in my bed, how would you react?  

622. How would you explain the political, international, historical systems on the earth to an alien? 

623. Can you win a ‘who eats most burgers’ contest?

624. How much money is enough money? 

625. Would you like it if you win the biggest loser competition? 

626. Dumbs or intelligence – who are mostly happier? 

627. Would you like to be the pet of another powerful caring creature? If not, why do you think our pets are liking it?

628. Why do we call it falling in love and not rising in it? 

629. If you had to choose between hurting yourself either physically or emotionally, what would you choose? 

630. Why do humans consider themselves wisest? 

631. Can you fall for someone even though by not meeting them for once?

632. What exactly does love mean? 

633. Can something like absolute freedom be real? 

634. Do you believe in conspiracy theories? 

635. If you could turn any one of the features of your pet humanlike, what would it be?

636. Do you think animals think we are adorable like we think of animals? 

637. What do you think is the sexiest color? 

638. Have you ever talked in length to the wrong number? 

639. What would you like to tell your ex for one last time? 

640. Do you think animals curse? Which animal is most likely to? 

Love Questions to Ask

What is the one topic that never gets old? Yes, love. So, when it’s about asking some rosy love questions, this list is going to be helpful, no doubt.

The only addition is – it will be helpful in understanding each others’ perspectives better. Give them a try. 

641. When was the last time you told your family that you love them? 

642. Have you met the love of your life? So, how did you realize this is it? 

643. What do you think makes love feel so overrated? Or, do you think it isn’t? 

644. What sounds like true love to you? 

645. If you had to give some real-life examples of love, what would it be? 

646. How much love matters in your life? 

647. Do you want to date before live or love before date? 

648. How do you usually show your love to someone? 

649. Do you like overt or physical displays of love? Or, are you more into subtle expressions? 

650. What is the best love confession according to you?

651. How can someone make you feel special? 

652. What cliches of love stories do you love? 

653. Are you romantic? 

654. What do you think is the most important element of love? 

655. How important do you think is sex in love?

656. Can love happen twice? 

657. Is it okay if someone loves more than one person at the same time? 

658. What is the happy ending for any love story? 

659. Do you have any romantic fantasies that you want to share? 

660. Can love make you a better person? 

Stupid Questions to Ask

Common sense is not so common. But so is stupidity. Especially in this ultra-modern competitive world where everyone wants to look smarter.

The good thing is – these stupid questions are super entertaining, funny, and great mood-lifters. So, here are some dumb random questions to make things go crazy! 

661. To whom would you like to have a secret love affair? 

662. What is the most challenging thing you’ve ever done? 

663. What is your favorite part of a pizza – crust, base, or toppings? 

664. How would you like to boast in front of your mean relatives?

665. When did you cry-laugh last? 

666. How self-aware are you? How do you know? 

667. What makes someone the worst 

668. If you had to choose one between toothbrush and toilet paper – what would you choose? 

669. Would you rather eat one thing all your life or eat a new thing every time you eat with no repetition ever? 

670. Do you like gossiping? 

671. If you meet your favorite villain character on the street, would you run or would you talk to them? Like, imagine the joker is behind you.

672. Have you ever overheard someone talking on the phone and found it quite interesting? 

673. If the devil was real, what chances is there for you to carry his genes? 

674. What if a fish has hydrophobia? 

675. Did you ever think that your reality might be a dream and what you dreamt could be a reality? Okay, let that sink in. 

676. How good are you at acting smart? 

677. If you could have any dumb superpower, what would it be? 

678. What was your dumbest decision ever? Okay, why do you think so?

679. Have you ever got weird looks from people because of something you said or did publicly? 

680. Are you confident in your words? Are you sure? 

Silly Questions to Ask

Let’s accept this -silly is interesting. Indeed, imagine the scene when you talk silly, ask questions that make no sense, and the conversation gets more and more giggle-worthy.

Yes, these silly questions are good for that mood. Here, taste a mouthful of silliness – 

681. Do you think being silly makes you adorable? 

682. Suppose you could get a million dollars if you never eat your favorite food again in life. Would you still take it?

683. If you could make a mandatory amount of alcohol consumption compulsory for a job, what would it be? 

684. Can you suggest a more controversial pizza topping than pineapple on pizza? 

685. If you could have one in real life, which mythical creature would improve your life significantly?

686. Suppose your life is a book. You are imported onto this page of someone else’s life mistakenly. Would you return to your book or would you prefer to go on with this one?

687. If you could sell any random thing as a piece of art, what would it be?

688. Answer to which one question is great to understand you as a person? 

689. If you could date anyone, living or dead, whom would you choose?

690. Would you like to be with your crush in a zombie apocalypse or a murder mystery? 

691. If animals could talk, who would sound like you? 

692. How good are you at procrastinating things? 

693. If you start a business in which you can catch someone’s soul every time users provide their email, what would you name your company? 

694. What sounds better – a night party and imported expensive wine or a beach party and local sweets? 

695. If you get a chance, would you like to be the president? 

696. What sounds like extreme power to you? 

697. If you had to make someone jealous, how would you do that? 

698. What decides if someone is dumb? 

699. If you had to make a flop movie, what would be its plot? 

700. What makes you more stupid than anyone else? Take it as a challenge and prove yourself dumbest. 

Tips to Ask Good Questions

You can turn any boring banter into an interesting conversation with the right conversation craft.

And it’s simple. Have fun. Be creative with the questions. Add follow-up questions. Be genuinely interested. Tada, it’s done! Plus, the above list of questions is going to help you out. 

Want a bit more? These well-thought tips would help you in mastering the art of asking questions. –

  1. Know your purpose. That is, what are you expecting from the conversation? Do you want to have a professional meetup or casually flirt? Make sure you ask questions accordingly.
  2. Be Confident. It’s crucial to make your questions sound impressive. 
  3. Add your perspective to the conversation. Like, tell how you would answer it. Also, don’t hesitate in adding questions from your mind. 
  4. Keep it open. Don’t ask questions back to back making it sound like an interview. Crack some jokes. Add other points. Thus, make it more natural.
  5. Respect their comfort zone. Sometimes, the other person doesn’t find it comfortable to get too personal or talk dirty out of nowhere. Proceed considering their willingness. 

Questions to Ask – Final Words

We all want to have impressive conversations. To connect, express, and grow. Here, questions become a powerful tool. And with the right questions, you can direct any situation towards your goal. 

However, it’s not the rule. Indeed, you can always go with the flow. Listen to your heart. And choose questions to ask people without much thought. Just make sure you both enjoy it!