Looking for the best questions to ask people to go deeper into their thoughts?
If you are sitting with the person and want to start a conversation that is both, thoughtful and meaningful, here we’ve compiled the list of the best questions to ask people that will turn ordinary discussions into extraordinary moments.
Scroll down to start a rich and meaningful discussion. Enjoy.
Very Good Questions to Ask
1. What are you interested in that most people aren’t?
2. What is the weirdest thing you have ever eaten?
3. What’s the fanciest event you’ve ever attended?
4. If you were given one thousand acres of land that you didn’t need to pay taxes on but couldn’t sell, what would you do with it?
5. What’s the weirdest text or email you’ve gotten?
6. What’s the most boring super hero you can come up with?
7. What’s the worst movie trope?
8. What would your perfect meal look like?
9. What habit do you have now that you wish you started much earlier?
10. What’s the worst hairstyle you’ve ever had?
11. What riddles do you know?
12. What goal do you think humanity is not focused enough on achieving?
13. If you were a ghost and could possess people, what would you make them do?
14. What was cool when you were young but isn’t cool now?
15. What’s the most ironic thing you’ve seen happen?
16. When was the last time you face palmed?
17. What’s one place you’ve visited that you never want to return to?
18. Which of your vices or bad habits would be the hardest to give up?
19. Do you get along with all your coworkers?
20. What’s the first thing you do after getting home from work?
21. What word is a lot of fun to say?
22. Who in your life has the best / worst luck?
23. What do you want people to say about you at your funeral?
24. Where’s the next place on your travel bucket list and why?
25. How do you take your coffee?
26. What was the last TV show you binge-watched?
27. Ideally, how would you spend your birthday?
28. How old were you when you started working?
29. How did your parents meet?
30. What’s some insider knowledge that only people in your line of work have?
31. If you could only eat one food for the rest of your life, what would it be?
32. What’s your favorite season and why?
33. What’s your ideal work-life balance?
34. What causes are you passionate about?
35. What’s your favorite place on earth?
36. What’s your most prized possession and why?
37. What was the best thing that happened to you today?
38. What would be some of the downsides of certain superpowers?
39. What are the most important qualities in a leader?
40. What are the songs that make you sing along whenever you hear them?
41. What word would friends of yours use to describe you? Do you agree or disagree?
42. What actors or actresses can’t play a different character because they played their most famous character too well?
43. What is the most absurd thing you’ve been tricked into doing or believing?
44. If you were moving to another country, but could only pack one carry-on sized bag, what would you pack?
45. What’s the best show on TV right now?
46. What has been your greatest kitchen mistake?
47. What would your perfect day look like?
48. How do you like to spend your free time?
49. What would your perfect day be like?
50. Where would you relocate if you were forced to leave the country?
51. What animal would be the most terrifying if it could speak?
52. What are the things you’d spend with a billion dollars?
53. Where do you get most of the decorations for your home?
54. What are your most important rules when going on a date?
55. How do you make yourself sleep when you can’t seem to get to sleep?
56. What is your favorite movie of all time?
57. Do you believe in soulmates?
58. What type of cuisine would you serve your customers if you own a five-star restaurant?
59. What was the last thing you read?
60. What’s the most overrated product out on the market?
61. What app can you not believe someone hasn’t made yet?
62. What’s your biggest pet peeve?
63. What is the weirdest text you have ever received recently?
64. How would your country change if everyone, regardless of age, could vote?
65. When was the last time you yelled at someone?
66. What food is delicious but a pain to eat?
67. What is your biggest regret in life?
68. Who was your craziest / most interesting teacher?
69. What fashion trend makes you cringe or laugh every time you see it?
70. What kinds of things do you like to cook or are good at cooking?
71. What naps are the most satisfying?
72. What’s your haunted house story?
73. What country is the strangest from your cultural stand point?
74. What are some red flags to watch out for in daily life?
75. What animal is the most majestic?
76. What was the happiest day of your life?
77. Should kidneys be able to be bought and sold?
78. What’s the most depressing meal you’ve eaten?
79. What social stigma does society need to get over?
80. What current trend do you hope will go on for a long time?
81. How do you enjoy spending your alone time?
82. What’s the funniest actual name you’ve heard of someone having?
83. Is this the career you saw yourself doing as a child?
84. Have you ever failed at something? What did you do after that?
85. When was the last time you felt you had a new lease on life?
86. What’s the best type of cheese for you?
87. What’s the most pleasant sounding accent?
88. What’s the best piece of career advice you ever got?
89. What’s the worst color that was ever invented?
90. What is the worst TV advertisement you’ve seen recently?
91. What’s your ideal first date?
92. What’s the funniest TV show you’ve ever seen?
93. If you were given the chance to make your one wish come true, what would it be?
94. What’s the worst backhanded compliment you could give someone?
95. What unethical experiment would have the biggest positive impact on society as a whole?
96. What’s the funniest word in the English language?
97. What mythical creature do you wish actually existed?
98. What are your hobbies, and how did you get into them?
99. What is on your bucket list?
100. What was something you thought was a career setback that actually turned out to be an opportunity?
101. Who is the most important person in your life and why?
102. What’s the most addictive game for you?
103. What TV show character would it be the most fun to change places with for a week?
104. What’s the most annoying noise?
105. What life skills are rarely taught but extremely useful?
106. What’s the one item of clothing you couldn’t live without?
107. Who has zero filter between their brain and mouth?
108. Who’s the messiest person you’ve ever known?
109. What is the greatest risk you have ever taken?
110. What’s the career highlight you’re most proud of?
111. Who would you want to trade lives with?
112. Do you have a mentor?
113. What originally got you interested in your current field of work?
114. What’s the worst gift you’ve ever received, and what did you do about it?
115. What’s your favorite sandwich and where did you eat it?
116. What are you most afraid of?
117. What’s the weirdest thing you’ve found lying on the ground / side of the road?
118. Which charity or charitable cause is most deserving of money?
119. Are you afraid of ghosts?
120. What’s the most embarrassing story from your childhood?
121. What’s your favorite board game?
122. What always cheers you up when you think about it?
123. What’s the coldest you’ve ever been?
124. What’s your best story of you or someone else trying to be sneaky and failing miserably?
125. What food should taste better than its appearance?
126. What’s something that everyone knows is true, but we don’t like to admit it?
127. Where do you see yourself in five years?
128. How would your 10-year-old self react to what you do now?
129. What’s your favorite content genre (horror, sci-fi, rom-com, etc.)?
130. What annoys you the most about your job?
131. Who do you go out of your way to be nice to?
132. Can you carry an elephant?
133. What’s the coolest animal you’ve seen in the wild?
134. What is something people would never guess just by looking at you?
135. Which instrument has the funniest sound?
136. Would you rather stay in or go out on a Friday night?
137. What was your most recent lie?
138. Which protagonist from a book or movie would make the worst roommate?
139. Which word would you use if you could only use one for the rest of your life?
140. What invention doesn’t get a lot of love, but has greatly improved the world?
141. Do you care about what other people tell you?
142. What’s the best career decision you’ve ever made?
143. What’s the worst career decision you’ve ever made?
144. What type of role do you want to take on after this one?
145. When was the last time you immediately regretted something you said?
146. How many close friends is ideal?
147. What’s the worst date you’ve ever been on?
148. What’s the best concert you’ve ever been to?
149. Which of the two smells better, fresh-cut grass or bread baking in the oven?
150. What goal do you want to accomplish in the next few years?
151. How many times has your heart been broken?
152. What was your first job?
153. What is one ability that you believe everybody should possess?
154. What activity instantly calms you?
155. What’s a common experience for many people that you’ve never experienced?
156. Have you ever made a decision that changed your life?
157. What’s the best gift you’ve ever received, and why?
158. What song always gets you out on the dance floor?
159. What’s something you wish you could change about yourself?
160. Do you like group activities, or prefer doing things solo?
161. Is there one job you’d never ever do?
162. What’s your favorite quote?
163. What’s the silliest thing you’ve seen someone get upset about?
164. Which celebrity do you think is the most down to earth?
165. What is the most amazing slow motion video you’ve seen?
166. Have you ever thought of what your future baby will be named?
167. What would you want people to say about you at your retirement party?
168. Do you like going to the movies or prefer watching at home?
169. Do you think that aliens exist?
170. What languages do you wish you could speak?
171. What are some clever examples of misdirection you’ve seen?
172. What are your pet peeves?
173. What’s your favorite board game?
174. What was your most embarrassing moment in grade school?
175. What would be the worst thing to hear as you are going under anesthesia before heart surgery?
176. What’s the dumbest thing someone has argued with you about?
177. What would be the click-bait titles of some popular movies?
178. Who or what never fails to make you laugh?
179. What’s the most addicted to a game you’ve ever been?
180. What career advice would you give to your younger self?
181. What did you Google last?
182. What game have you spent the most hours playing?
183. What is something that’s true that nobody agrees with you on?
184. What would a world populated by clones of you be like?
185. What do you remember most about your first job?
186. What’s about to get much better?
187. Are you more of a “work to live” or a “live to work” type of person?
188. How do you approach taking time off from work?
189. What’s your best story from a wedding?
190. What period would you travel to if you were given a time machine?
191. What do you do on your commute to/from work?
192. What was the last song you sang along to?
193. What makes you laugh the most?
194. If you could save one material thing from a fire, what would you save?
195. What are some misconceptions about your hobby?
196. What are you currently worried about?
197. What sport will be invented next?
198. If you could meet anyone in this world today, who would you meet?
199. What animal would be cutest if scaled down to the size of a cat?
200. Which celebrity or band has the worst fan base?
201. What “old person” things do you do?
202. What’s the hardest you’ve ever worked?
203. What’s the most expensive thing you’ve broken?
204. What’s your favorite way to spend a day off?
205. Are you able to work from home, and if so, do you enjoy it?
206. Do you think that children born today will have better or worse lives than their parents?
207. If magic was real, what spell would you try to learn first?
208. Who in your life most makes you feel a sense of home?
209. What movie universe would be the worst to live out your life in?
210. Out of the four seasons, what’s your favorite one?
211. Do you believe in having a “five-year plan”?
212. What’s the best thing you’ve read in the last five years?
213. When was the last time you were snooping, and found something you wish you hadn’t?
214. What was the best vacation you ever took and why?
215. What is the dumbest way you’ve been hurt?
216. Who is your all-time favorite Disney character?
217. What movie quotes do you use on a regular basis?
218. What did you think was going to be amazing but turned out to be horrible?
219. What’s the most interesting building you’ve ever seen or been in?
220. What are the three scents you like?
221. What was the most life-changing event in your life so far?
222. Do you eat food that’s past its expiration date if it still smells and looks fine?
223. What’s something you really resent paying for?
224. What’s the most important thing you’ve ever done at work?
225. If you were given the chance to steal something, what would it be?
226. What’s the most comfortable bed or chair you’ve ever been in?
227. What’s something that everyone, absolutely everyone, in the entire world can agree on?
228. What are you most thankful for?
229. What food do you crave most often?
230. If you could only bring three things with you on a deserted island, what would you pick?
231. What’s the funniest joke you know by heart?
232. What songs hit you with a wave of nostalgia every time you hear them?
233. What is the first thing you do after getting home from a trip?
234. What would be the first thing you’d do if you won the lottery?
235. What’s the hardest challenge you overcame?
236. If you could only teach three things to your future child, what would they be?
237. What’s your favorite thing about yourself?
238. What’s your cure for hiccups?
239. What’s the best / worst practical joke that you’ve played on someone or that was played on you?
240. If you could hack into any one computer, which computer would you choose?
241. When was the last time you got to tell someone “I told you so.”?
242. What’s the funniest comedy skit you’ve seen?
243. What’s an essential part of your daily routine?
244. What’s your favorite thing about your current job?
245. Do you like coffee or tea better?
246. What’s the most creative use of emojis you’ve ever seen?
247. Do you have a favorite type of exercise?
248. Where are some unusual places you’ve been?
249. If you were given five million dollars to open a small museum, what kind of museum would you create?
250. Have you ever had a side hustle or considered having one?
251. What are the hobbies you want to develop?
252. What was the most unsettling film you’ve seen?
253. What’s the funniest thing you’ve done or had happen while your mind was wandering?
254. Are you into podcasts or do you only listen to music?
255. What’s the most interesting documentary you’ve ever watched?
256. Who or what inspires you in your career?
257. What do you feel most passionate about?
258. What is the best concert you have ever been to?
259. What’s the most exciting part of your job?
260. Do you consider yourself good at networking?
261. What character in a movie could have been great, but the actor they cast didn’t fit the role?
262. Where’s your go to restaurant for amazing food?
263. What makes you roll your eyes every time you hear it?
264. What food have you never eaten but would really like to try?
265. What’s your favorite podcast?
266. What’s the opposite of a koala?
267. What’s the spiciest thing you’ve ever eaten?
268. What weird food combinations do you really enjoy?
269. What type of music are you into?
270. What was the best meal you ever ate?
271. What animal or plant do you think should be renamed?
272. What do you usually do during weekends?
273. What did teachers used to say about you on your report card—and is it still true?
274. What problem are you currently grappling with?
275. Do you have a favorite holiday? Why or why not?
276. Do you actively post on social media?
277. When did something start out badly for you but in the end, it was great?
278. What are those things you’re too old to do but you still enjoy?
279. What bit of trivia do you know that is very interesting but also very useless?
280. What was the last photo you took?
281. What’s the phone app you use most?
282. What really needs to be modernized?
283. What do you think you are much better at than you actually are?
284. What is your relationship like with your co-workers?
285. How do you judge a person?
286. Do you have a morning routine at work? If so, what it’s like?
287. What’s the best lesson you’ve learned from a work of fiction?
288. What’s the smartest thing you’ve seen an animal do?
289. What has been blown way out of proportion?
290. What’s the most ridiculous thing you have bought?
291. Have you ever broken up with a friend, and why?
292. Who do you wish you could get back into contact with?
293. What’s the worst movie you ever saw?
294. What’s something an outsider wouldn’t know about your industry?
295. What outdoor activity haven’t you tried, but would like to?
296. What’s the craziest bet you have ever made?
297. Where do you get your news?
298. Would you rather have intelligence over looks?
299. What’s your funniest story involving a car?
300. Who is your greatest enemy?
301. Would you say you’re more of an extrovert or an introvert?
302. What’s the first thing you pack for an out-of-the-country flight?
303. What word do you always misspell?
304. What obstacles would be included in the World’s most amazing obstacle course?
305. What’s the craziest conversation you’ve overheard?
306. What’s something that all your friends agree on?
307. If someone narrated your life, who would you want to be the narrator?
308. Do you believe that love is blind?
309. What tips or tricks have you picked up from your job / jobs?
310. Do you collect anything?
311. What’s the food you usually refuse to share?
312. What was your favorite age growing up?
313. What would be the best thing you could reasonably expect to find in a cave?
314. What’s your least favorite genre of music?
315. What does your dream life look like?
316. What about humans confuses you the most?
317. When was a time you acted nonchalant but were going crazy inside?
318. What’s your favorite karaoke song?
319. What’s the worst job you’ve ever had?
320. Would you rather cook or order in?
321. Would you rather be hot or cold?
322. What is the best compliment that you’ve ever received?
323. Does your job make you feel happy and fulfilled? Why or why not?
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