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Questions to ask

Each question here is specific enough that the answer is a story, which is what keeps a conversation going. Pick a list for the person in front of you: someone new, an old friend, a partner or a child.

Questions to Ask lists

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How to use these questions

1. Choose a list that fits who you're talking to.
2. Take turns drawing a question. The person who draws it asks, and everyone else answers.
3. Ask one follow-up before moving on. The follow-up is usually where the good part is.

Updated November 2026.

1. What sound takes you straight back to the home you grew up in?
2. What did your bedroom look like when you were ten?
3. What's the first thing you bought with money you earned yourself?
4. What job did you want at age seven, and what happened to that plan?
5. What food did you hate as a kid and love now?
6. What's the most useful thing someone taught you in under five minutes?
7. What's hanging on your walls at home, and how did it get there?
8. What's the first song you played on repeat until someone begged you to stop?
9. What's the best meal you've ever eaten, and who was at the table?
10. What small thing reliably rescues a bad day for you?
11. What's the strangest job you've had or nearly took?
12. Where did you go on your first trip without your family?
13. What skill do you have that almost never comes up?
14. What were you known for in school?
15. What does your family do that other families find odd?
16. What was the best thing about the street you grew up on?
17. What's the last thing you couldn't wait to tell someone about?
18. What hobby did you drop that you still think about?
19. What movie have you seen so many times you can say the lines?
20. What song would you pick for karaoke with the whole room watching?
21. What does a perfect Saturday morning look like for you?
22. What are you weirdly competitive about?
23. What's the oldest thing you own and still use?
24. Who was the first friend you ever made, and how did it start?
25. What were you doing the last time you completely lost track of time?
26. What's the best advice you ignored at first?
27. What word or phrase do you say too much?
28. Where would you move tomorrow if work didn't matter?
29. What did you get in trouble for most as a kid?
30. What food from your hometown do people elsewhere get wrong?
31. What's the last thing you learned just because you were curious?
32. What subject could you give a ten-minute talk on with no notes?
33. Which teacher do you still remember, and what did they do?
34. What compliment did you get years ago and still remember?
35. What kind of kid were you at birthday parties?
36. What's the most out-of-character thing you've ever done?
37. What was your first email address or screen name?
38. What's the longest you've gone without your phone, and how did it go?
39. What was the first concert or live show you went to?
40. What are you a snob about?
41. What show have you pushed on everyone you know?
42. What's the best view you've ever woken up to?
43. What did you collect as a kid, and where is it now?
44. What rule do you live by that you made up yourself?
45. Who in your family are you most like?
46. How did you get your name?
47. What's the nicest thing a stranger has done for you?
48. What can you cook without a recipe?
49. What's the worst haircut you've ever had?
50. What did you do the summer after you finished school?
51. What did you believe as a kid that turned out to be completely wrong?
52. What's your idea of a great night in?
53. What were you like at fifteen?
54. What sport or game are you better at than people expect?
55. What's the picture on your phone's lock screen, and why that one?
56. What have you changed your mind about in the last few years?
57. Who's your oldest friend, and how did you two meet?
58. What sound do you love that most people never notice?
59. What's the first thing you remember being proud of?
60. What do your friends tease you about?
61. What place from your childhood no longer exists?
62. What snack did you beg for as a kid?
63. What's the best thing you've found by accident?
64. Which holiday tradition would you never give up?
65. What language would you love to wake up fluent in, and where would you go first?
66. What was your first pet's name, and who chose it?
67. What tiny luxury would you miss most on a camping trip?
68. What were family dinners like in your house growing up?
69. What do people usually get wrong about you at first?
70. What's the last thing that made you laugh until it hurt?
71. What game did you play for hours as a kid?
72. What's the best decision you made in the last year?
73. What did you want to be famous for when you were little?
74. What wrong turn or detour turned into a good story?
75. What's the most spontaneous thing you've done on a trip?
76. What job would you be terrible at?
77. What do you miss about being a teenager?
78. Who taught you to ride a bike or swim, and how did it go?
79. What's the first thing you'd show a visitor in your hometown?
80. What did you eat at your grandparents' house that you've never had anywhere else?
81. What's the best thing you learned from a job you didn't like?
82. What's in your bag or pockets right now that says something about you?
83. Where were you nervous to go that you ended up loving?
84. What do you always pack that other people think is odd?
85. What moment would you relive exactly as it happened?
86. Who believed in you before you'd done anything to earn it?
87. What were you sure about at twenty that you're less sure about now?
88. Which goodbye do you still think about?
89. What did you learn at your family's kitchen table that you still use?
90. What's the hardest thing you've ever had to say out loud?
91. What risk didn't you take that you still wonder about?
92. What would your grandparents be most surprised by in your life?
93. What kindness did you never get to say thank you for?
94. What were you afraid of as a child that you still feel a little of?
95. What did you have to learn the hard way?
96. What do you hope people say about you after you leave a room?
97. When did you first feel like an adult?
98. Where do you feel most like yourself?
99. Which of your parents' habits have you caught yourself repeating?
100. What promise did you make to yourself and keep?
101. What do you wish someone had told you at sixteen?
102. Who do you miss that you could still call?
103. What did you forgive that you didn't expect to?
104. What small moment changed the direction of your life?
105. What would you do with a year off and no one to answer to?
106. What are you proud of that you rarely get to mention?
107. What fear have you outgrown, and what replaced it?
108. What lesson do you keep having to relearn?
109. What did you once want badly and are now glad you didn't get?
110. What's the bravest thing you've seen someone else do?
111. What part of your younger self do you miss?
112. What does home mean to you now compared with ten years ago?
113. What question do you wish people asked you more often?
114. Which ordinary day from your past would you give a lot to have again?
115. Who shaped your idea of what a good person looks like?
116. What have you stopped apologizing for?
117. Which memory gets better every time you tell it?
118. What's the best mistake you ever made?
119. What would ten-year-old you think of your life today?
120. What do you want to be doing on an ordinary Tuesday ten years from now?
121. Which tradition do you want to pass on, and which one ends with you?
122. What compliment do you find hard to believe?
123. What's the longest you've held a grudge, and how did it end?
124. When did someone's honesty sting and help at the same time?
125. What do you know about friendship now that you didn't at eighteen?
126. What scares you about getting what you want?
127. Who would you most like to make proud, and why them?
128. What did you give up on that deserves another try?
129. What song can change your mood in ten seconds, and what's the memory behind it?
130. Where were you the last time you felt completely free?
131. What's the kindest thing you've done that nobody knows about?
132. What did you used to think about yourself that turned out to be wrong?
133. Which conversation changed how you see someone?
134. What do you think you'll be nostalgic for about right now?
135. What did your parents get right that you only noticed later?
136. When do you feel most understood?
137. Which closed door turned out to be a favor?
138. What would you like to be brave enough to try?
139. What book, film or song found you at exactly the right time?
140. What hard stretch are you now grateful for?
141. Which friend has changed you the most, and how?
142. What do you do when no one needs anything from you?
143. What do you want more of in your life, and what's in the way?
144. What do you wish you could tell someone who's no longer around?
145. What was the first big choice you made that was truly your own?
146. What moment made you realize your parents were just people?
147. What have you made that you hope outlasts you?
148. When were you last moved by a stranger?
149. Which regret taught you something useful?
150. What would you study if grades and careers didn't exist?
151. What do you find hard to ask for?
152. What beautiful thing did you see this week that most people walked past?
153. What's the most important thing an older person ever told you?
154. What object do you keep only because of the story behind it?
155. Which job, place or person did you leave at the right time?
156. When did you last do something for the first time?
157. What's the dumbest accident you've ever had?
158. What's the worst thing you've ever cooked, and who had to eat it?
159. If your pet could talk, what secret would it tell first?
160. What's the most embarrassing thing you've said to a teacher or a boss?
161. What would your wrestling name be, and what's your finishing move?
162. What's the weirdest thing you've eaten on a dare?
163. What totally useless talent are you proud of?
164. What would a documentary about your worst week be called?
165. What did you think adults did all day when you were a kid?
166. Which animal would make the worst waiter?
167. What's the most ridiculous argument you've ever won?
168. What's the lamest excuse you've given for being late?
169. What smell do you secretly like that you probably shouldn't?
170. What would you be arrested for if being annoying were a crime?
171. What's the worst gift you've had to pretend to love?
172. What would your warning label say?
173. What's the strangest thing you've done while half asleep?
174. Which vegetable would win in a fight, and why?
175. What's the worst fashion choice you ever made on purpose?
176. What song do you know every word to and wish you didn't?
177. What did you do as a kid that you thought was genius?
178. What tiny inconvenience would turn you into a villain?
179. What's the least impressive thing you've ever bragged about?
180. What sound effect should play every time you walk into a room?
181. What's the funniest thing you've overheard in public?
182. If you were a ghost, how would you annoy the people in your house?
183. Which chore would you make an Olympic sport, and would you medal?
184. What's the most pointless thing you've ever cried about?
185. What do you sing in the shower when you think nobody can hear?
186. What's the worst name you've given a pet, a toy or a car?
187. If you were a sandwich, what would be in you?
188. What's the silliest thing you're scared of?
189. What's the weirdest dream you can still remember?
190. What's the worst pickup line you've heard or used?
191. What did you pretend to understand for far too long?
192. Which cartoon character would be the worst roommate?
193. What's the longest you've kept a lie going about something tiny?
194. What food opinion will you defend to the end?
195. What's the worst movie you love anyway?
196. What would be your first law as ruler of a very small island?
197. What's the funniest way you've ever been woken up?
198. What's the most childish thing you still do?
199. What would the trophy say if you won an award for your worst habit?
200. What nickname do you hope never comes back?
201. If you had to wear one costume to work for a year, what would it be?
202. What two foods do you mix that make other people leave the table?
203. What's the worst thing you could say in a wedding toast?
204. What did you think was fancy when you were a kid?
205. What's the strangest place you've ever fallen asleep?
206. What's the worst text you've ever sent to the wrong person?
207. Which animal could you beat in a race, and which one would humble you?
208. What's the pettiest reason you've ever stopped liking someone?
209. What do you do in the car that you'd deny in court?
210. What's the most useless fact you know by heart?
211. What would you do with one day of being invisible?
212. What's your go-to dance move, and who has been hurt by it?
213. If your stomach could file a complaint about you, what would it say?
214. What's the weirdest thing you've looked up this month?
215. What's the most elaborate plan you've made to avoid a small task?
216. Which rule in your childhood home made no sense?
217. What would you put on a billboard just to confuse people?
218. What's the strangest thing in your fridge right now?
219. What do you do at home that would look very strange to a visitor?
220. What's the most ridiculous thing you've done to impress someone?
221. What everyday object took you embarrassingly long to figure out?
222. What would your pirate name be, and what would you refuse to steal?
223. When were you the most confident you've ever been while completely wrong?
224. Which piece of furniture in your home knows the most gossip about you?
225. What would you bring to a potluck to make sure you're never invited back?
226. What's the worst thing you've said while trying to be polite?
227. What's your first memory of me?
228. What did you think of me before we became friends?
229. Which of us would last longest on a desert island, and who's out first?
230. What's the best night out we've ever had together?
231. What story about us do you tell other people?
232. Who in our group would you call first at 3 a.m. with a flat tire?
233. What do I do that you've quietly copied?
234. What's the worst idea we've ever had together?
235. Which friend of ours gives the best advice, and who gives the worst?
236. What have you never told me because it seemed too small to mention?
237. What's the hardest we've ever laughed together?
238. If our group were a sitcom, who would play which part?
239. Which habit of mine would you change if you could pick one?
240. What do you think I'll be like at eighty?
241. What's the nicest thing a friend did for you that they've probably forgotten?
242. Who in this group is most likely to end up famous, and for what?
243. When did I annoy you and you let it slide?
244. What's our best inside joke, and how did it start?
245. Which of us is the worst driver, and what's the proof?
246. What hidden talent does one of us have that deserves more attention?
247. What's the most trouble we've been in together?
248. What song will always make you think of our group?
249. What am I better at than I give myself credit for?
250. What job would each of us have in a heist?
251. When were you really proud of one of us?
252. What's the worst outfit you've ever seen me leave the house in?
253. Which of us would survive a horror movie, and who trips in the first scene?
254. What do we always say we'll do and never do?
255. What did we fight about that seems ridiculous now?
256. How have I changed since we met?
257. If we opened a business together, what would it be, and who gets fired first?
258. When did you need a friend and one showed up?
259. Which of us would be the strictest parent?
260. What rumor about you from school should I know?
261. What's your favorite detail about how we met?
262. Who in the group has the best taste in music, and who should never get the speaker?
263. What's the last thing one of us did that was completely in character?
264. What do you want us to still be doing together in twenty years?
265. Who takes longest to get ready, and who's always waiting in the car?
266. What's the most embarrassing thing you've seen me do?
267. What phase did one of us go through that we should never forget?
268. What have you borrowed from a friend and never returned?
269. When did you know we'd be friends for a long time?
270. What group tradition should we start this year?
271. Who's most likely to get us lost, and who gets us home?
272. What's the funniest moment of ours that nobody got on camera?
273. What do you admire in a friend that you've never told them?
274. Who's the worst cook in the group, and what's the evidence?
275. What do only your oldest friends know about you?
276. What's your role in this friend group, in your own words?
277. What do you think each of us was like at age eight?
278. Which friendship did you lose that you still think about?
279. What's the kindest lie a friend has ever told you?
280. Who here would you trust to plan your birthday, and who gets no say?
281. What bad decision did a friend talk you out of?
282. What's the best thing a friend ever talked you into?
283. What's the longest we've gone without talking, and who broke the silence?
284. Which of us would do best on a quiz show, and in what category?
285. What did you learn from a friend's family that yours never taught you?
286. What do you bring to a friendship that you're proud of?
287. What's the weirdest thing we both like?
288. What message from a friend made your whole week?
289. Who in the group is most likely to cry at a commercial?
290. What's your favorite memory with a friend from before you turned twelve?
291. What am I wrong about that you've stopped arguing over?
292. Which of us would you send to talk our way out of trouble?
293. What did one of us say years ago that we still quote?
294. What's the best thing we ever did with no budget and no plan?
295. What story would you tell in a toast about me?
296. When did you first notice me, and what went through your head?
297. What small thing do I do that makes you feel loved?
298. What's your favorite ordinary day we've had together?
299. What did you tell your friends about me after our first date?
300. What do we do now that would have surprised us in our first month?
301. Where should we wake up on our next anniversary?
302. Which habit of mine seemed odd at first and now you like?
303. What song makes you think of us?
304. When did you know this was more than a crush?
305. What's the best meal we've cooked together, and who did the real work?
306. What did I say early on that stuck with you?
307. What do we do better as a team than either of us does alone?
308. Which trip of ours would you repeat day for day?
309. What's the funniest fight we've ever had?
310. What do you want our home to feel like when people walk in?
311. When do you feel closest to me?
312. What was going through your head the first time you met my family?
313. Which photo of us do you love, and what was happening just outside the frame?
314. What do I do that makes you laugh every time?
315. What surprise could I plan that you'd love?
316. Which of our early dates would you redo, and what would you change?
317. What do you think we'll bicker about when we're old?
318. What's your favorite thing for us to do that costs nothing?
319. When were you proud to be with me?
320. What did you worry about at the start of us that turned out fine?
321. What does a perfect lazy Sunday with me look like?
322. What would you like me to ask you about more often?
323. Who said "I love you" first, and what's your version of the story?
324. Which chore would you happily trade me forever?
325. What place feels like ours?
326. What dream of yours could I help with?
327. What nickname for me do you only use in your head?
328. How do you know I've had a bad day before I say anything?
329. What would our friends say is the most typical thing about us as a couple?
330. What memory of us do you replay when we're apart?
331. What would be on the menu for our perfect dinner at home?
332. What part of our routine would you miss most if it changed?
333. What skill should we learn together?
334. What movie or show will always be ours?
335. What's the scariest thing we've done together that we'd do again?
336. When did you first feel at home with me?
337. What about me took you a long time to understand?
338. What place from your childhood would you like to show me?
339. Which of us is the better liar, and how do you know?
340. What compliment about me have you kept to yourself?
341. What do I do that drives you a little crazy and that you'd miss?
342. If we got a dog tomorrow, what would we name it and who would walk it?
343. What have you wanted to ask me and haven't?
344. What do you want us to be like at seventy?
345. What's the worst date we've had that makes the best story?
346. When did you know you could count on me?
347. What did your parents do as a couple that you want for us?
348. What smell or place takes you straight back to our early days?
349. What do you think I'm thinking about when I go quiet?
350. What's the nicest thing someone has said about us?
351. Which holiday would you like us to spend completely differently?
352. What did you first notice about how I treat other people?
353. What small ritual of ours would you defend against anyone?
354. What do you love about how we say goodnight?
355. Which of us fell first, and which fell harder?
356. What did I teach you to like?
357. What tiny thing about living with me did you not expect?
358. What would our theme song be on a good day, and on a bad one?
359. What's the best thing about coming home to me?
360. What do you admire about how I handle hard days?
361. What are we like on a long car ride, and who controls the music?
362. What do you remember about the first time we held hands?
363. What were you wearing the first time we met, and what was I wearing?
364. When were we completely in sync without saying a word?
365. What would you write in a note to hide in my coat pocket?
366. What do I do in my sleep that you've never told me about?
367. What's the best first date you can imagine that doesn't involve a restaurant?
368. What's the first thing you notice about someone you like?
369. What cheesy romantic thing do you secretly enjoy?
370. What small gesture wins you over every time?
371. What song would go first on a playlist for someone you like?
372. What's your most charming bad habit?
373. What's the best compliment someone could give you?
374. What would we be doing right now if we'd met on vacation?
375. What tells you early on that someone is worth your time?
376. What's your move when you want someone to notice you?
377. What's the most romantic place you've ever been?
378. Which movie scene sums up your idea of romance?
379. What makes you nervous in a good way?
380. What do you find attractive that has nothing to do with looks?
381. What's the most awkward first date moment you've lived through?
382. What gives you away when you like someone?
383. What would you cook to impress a date?
384. What's the sweetest thing someone has done to get your attention?
385. What question do you wish a date would ask you?
386. What do your friends say about your taste in people?
387. Where would you take me if you had one afternoon to show me your town?
388. What tiny thing can someone do that you find ridiculously cute?
389. What's your favorite way to spend an evening with someone you like?
390. What were you like the last time you had a crush?
391. What's the boldest thing you've done to talk to someone you liked?
392. What do you think we'd argue about on a road trip?
393. What's the fastest way to make you smile on a bad day?
394. What would you like us to try together that neither of us has done?
395. Who was your first crush, and what did you do about it?
396. What tiny detail about a person do you always remember?
397. What makes you feel comfortable around someone right away?
398. What would a perfect second date look like if the first went well?
399. What kind of message makes you grin at your phone?
400. What should I know about you before a third date?
401. Which date idea only works in the rain?
402. What could you teach me in ten minutes?
403. What would you bring to a picnic to impress me?
404. What did you almost say to me and then didn't?
405. Which hobby makes a person instantly more attractive to you?
406. Which of your stories do you save for people you want to impress?
407. What are you hoping I'll ask you?
408. What's the last thing that gave you butterflies?
409. What snack would we fight over at the movies?
410. What's the best date you've ever planned or been taken on?
411. How do you act around someone you like compared with everyone else?
412. What's the nicest thing someone has noticed about you?
413. What would you order for me if I let you pick everything?
414. What's your favorite thing anyone has ever called you?
415. If you could have any animal as a pet, what would it be and where would it sleep?
416. What would you teach if you were the teacher for one day?
417. What's the best thing in your lunchbox, and what would you trade away?
418. If your toys came alive at night, what would they do first?
419. What would you name a pet dragon, and what would you feed it?
420. What's the funniest thing that has ever happened at school?
421. Which superpower would be the most fun at recess?
422. What would you build with a million building blocks?
423. What's your favorite game to play at recess, and how do you play it?
424. If you could make one new school rule, what would it be?
425. What would be inside your dream treehouse?
426. Who is the kindest person in your class, and what do they do?
427. Which animal would cause the most trouble on a school bus?
428. What's the best thing you've ever made with your own hands?
429. If you were in charge of school lunch, what would be on the menu?
430. What do you think your pet does when everyone leaves the house?
431. What's the hardest thing you've learned to do?
432. What would your very own planet look like?
433. What job would you like when you grow up, and what's the best part of it?
434. What's the best story anyone has ever read to you?
435. What would you put in a time capsule for kids in the future?
436. If you shrank to the size of an ant, where would you explore first?
437. What did a friend do that made you really happy?
438. What's the silliest face you can make, and who taught it to you?
439. What would you invent to make mornings easier?
440. Which animal would you swap lives with for a week?
441. What would you do on a snow day with no rules?
442. What food would you make everyone in the world try?
443. What's the bravest thing you've ever done?
444. If you opened a store, what would it sell?
445. What do grown-ups do that makes no sense to you?
446. What would your robot helper do for you?
447. What sound always makes you laugh?
448. What would you do if you found a door in your room that wasn't there yesterday?
449. What's the coolest thing you learned this week?
450. Who makes you laugh the most, and how do they do it?
451. What would you cook for dinner if you were the chef tonight?
452. What's the best fort you've ever built, and what was it made of?
453. What would you ask a dinosaur if it could talk?
454. What game did you make up yourself, and what are the rules?
455. What makes you feel better when you're sad?
456. What do you want to be really good at someday?
457. If you could paint your room any way you like, what would it look like?
458. What's the best birthday you've had so far?
459. What would you pack for a trip to the moon?
460. What's the nicest thing you did for someone this week?
461. Which animal are you most like, and why?
462. If it could rain anything except water, what should it rain?
463. What's the first thing you'd do if you woke up as a cat?
464. What can you do now that you couldn't do last year?
465. Which rule at home would you change, and what would you swap it for?
466. If you wrote a book, what would it be about?
467. What's the best hiding spot you've ever found?
468. What would your dream playground have in it?
469. Which subject at school would you make twice as long?
470. What's the funniest word you know?
471. What would you do with a whole day at home and no screens?
472. If your favorite toy had a job, what would it be?
473. What's your favorite smell in the whole world?
474. What would you plant in a magic garden?
475. What do you think clouds taste like?
476. What's your favorite thing to do with a grown-up in your family?
477. What do you think your teacher does on the weekend?
478. What would your pet say about you if it wrote your report card?
479. What do you wish grown-ups would ask you about?
480. If you could add one new holiday to the calendar, what would everyone do on it?

Tips for a better game

• Answer the question yourself too. People open up more when the asker goes first.
• Skip any card without explaining why. Nobody owes an answer.
• On a long drive or a quiet dinner, put the phone in the middle and let each person draw one.

What is a conversation starter?

A conversation starter is an open question that invites a story or an opinion and has no right answer. People use them on dates, with friends and family, and in the game 21 Questions.

Questions people ask

What is the 21 Questions game?

Two people, or a group and one person in the hot seat, take turns asking questions until 21 have been answered. Every question must be answered honestly, and most groups allow one pass. The 21 Questions list on this page has questions that work for it.

What are good questions to get to know someone?

Ask about specific things: a first job, a food they could eat every day, the best trip they have taken. Specific questions get stories. Broad ones like "tell me about yourself" get short answers.

Are the questions for couples explicit?

No. They are about memories, habits, plans and what you like about each other. Some are romantic and none are explicit.

What are some good questions to ask?

Five from this list: What compliment did you get years ago and still remember? Where were you the last time you felt completely free? What's the worst thing you've said while trying to be polite? What would you like me to ask you about more often? If your toys came alive at night, what would they do first?

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