430 Good Questions to Ask Someone

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Good Questions to ask – Here i have prepared a list of questions to ask someone in a conversation that will prolong it in a healthy way. Plus i have Aggregated some tips to maintain the conversation for a longer period of time without boring them to death. So, Let’s not wait and jump right to it.

Tips to keep the conversation going

These tips helps me keep the conversations healthy and non boring. Here they are…

Use Conversation Openers

What is the best conversation opener you have ever heard?

The hardest part of a conversation is the opener. We tend to agonize over who and how to approach someone for a conversation. But don’t worry! A few conversation starters are the easiest way to get the chit chat ball rolling.good questions to ask

Plan your questions

Before your meeting, outline your information goals and a sequence of related questions to help you follow the conversation and cue your notes.

Know your purpose

Every question you ask should help you gather either facts or an opinion. Know which kind of information you need and frame your questions accordingly.

Speak your listener’s language

Relate questions to the listener’s frame of reference and use words and phrases that your listener understands. For example, avoid industry jargon when you’re negotiating with someone outside your industry. If someone doesn’t seem to understand what you’re asking, try rephrasing.

Use neutral wording

Asking leading questions, such as “How’d you like the terrific amenities at that conference center?” is unproductive. Because the question expresses a glowing opinion of the venue, the other person isn’t likely to say anything negative about it, even if he hated the place.

Focus your questions so they ask one thing at a time. To get more complete answers, craft short questions, each of which covers a single point. If you really want to know two different things, ask two different questions.

Don’t interrupt

Listen to the full answer to your question. The art of good questioning lies in truly wanting the information that would be in the answer.

Practice, practice, practice

I know many people which had huge problems with keeping conversations going and now, they can do this even with the most shy or uncooperative person. How did they manage to get to this point? They’ve practiced.

Lead with a compliment

Compliments are the best possible way to begin a conversation. Not only do they provide a perfect opening line and a possible door for discussion, they also make the person feel good about themselves. Starting the conversation off on a positive note is crucial to keep the conversation going.

Be nice.

This should be obvious, but don’t neglect it. Your level of friendliness can make or break the receptiveness of the other party involved. Walk into the conversation with a big smile and open body language, and keep yourself open, receptive and smiling politely for as much of the conversation as you can.

Keep it light.

Try to keep the conversation as light and approachable as possible. If you immediately start complaining about your job or talking about what’s wrong with your life, people will want to avoid you. If you tell a joke or an amusing story, they’ll be far more likely to stay.good questions to ask 3

Good Questions to ask in a Conversation

  1. What is the most expensive thing you’ve ever lost?
  2. Have you ever been totally wrong about something you were sure you were right about?
  3. Do you believe aliens exist?
  4. What would be the title of the movie of your life?
  5. What is your favorite smell?
  6. If you could create a job based on your biggest talent, what would you be?
  7. What is the scariest animal in the world?
  8. What is the scariest insect in the world?
  9. What book do you wish you had read even though you don’t want to read it?
  10. What bizarre food pairing do you love?
  11. What is legal that should really be illegal?
  12. What is illegal that should be legal?
  13. If you could have a Ph.D. in anything, what would it be?
  14. Would you rather go back in time or forward in time?
  15. What job do you think won’t exist anymore in the future?
  16. What is one word to describe the country you’re from?
  17. If you could classify people as being 2 types, what would they be?
  18. Have you ever had a “this could only happen in the movie” moment?
  19. If you could ask one person one question and they would answer honestly, what would you ask and who would you ask?
  20. What animal would you want to have as a pet if you could choose anything?
  21. What is the best movie introduction of all time?
  22. If you could switch lives with anyone for a day, who would it be?
  23. What is something we will never know the answer to?
  24. What’s the coolest thing you own?
  25. If you were stuck on a deserted island, what is the one thing you couldn’t live without?
  26. What’s your favorite hobby?
  27. You have an hour of free time- what do you do?
  28. What was your favorite book as a kid?
  29. What’s the best gift you’ve ever given someone?
  30. What is one thing you still have from your childhood?
  31. What from your childhood are you most nostalgic for?
  32. What would you want to come back as in your next life?
  33. If you could get a completely truthful answer to one question, what would you ask?
  34. Which personality trait of yours has served you the best in life?
  35. What do you wish people would stop talking about already?
  36. What is the best prank you’ve ever pulled on someone?
  37. Do you collect anything?
  38. What’s something you lose all the time?
  39. If you ran the world, what rule would you enact?
  40. Do you believe in free will or destiny?
  41. What was your happiest age?
  42. Who’s your biggest role model?
  43. What’s your favorite part of your job?
  44. If you could have coffee with anyone living or dead, who would it be?
  45. What advice would you give your 13-year-old self?
  46. What’s the best advice you’ve ever received?
  47. What’s the best advice you could give your future children?
  48. What’s the most worn item in your closet?
  49. What’s the best meal you’ve ever had?
  50. What was the most disappointing meal you’ve ever had?
  51. What’s the most dangerous thing you’ve ever done?
  52. If you were given three things to make you happy, what would these be?
  53. How would you rank the following in importance: family, career, love life?
  54. Which would you prefer: having a baby without a partner or a partner without a baby?
  55. What was your experience about being “mansplained,” and what did you do about it?
  56. Who was your favorite cartoon character when you were a kid?
  57. Do you think God is real, and why?
  58. Do you believe in giving people second chances, and why?
  59. How would you describe your first crush?
  60. What book influenced you the most?
  61. What life-changing event have you experienced?
  62. What’s a deal-breaker for you in a relationship?
  63. Are you a morning or a night person?
  64. How important is trust in a relationship?
  65. How do you feel about infidelity?
  66. Do you believe that the day will arrive when humans will be replaced by machines in almost all aspects of life?
  67. What do you think is humankind’s greatest invention?
  68. Do you think that humans are doing more harm than good to the planet?
  69. What is your take on telepathy?
  70. What is your favorite workout routine?
  71. Would you rather be called vain or insecure?
  72. What important lesson did a close relative teach you?
  73. What part of your body do you find attractive?good questions to ask 1
  74. Which would you choose to be: law-abiding citizen or rule breaker, and why?
  75. What is your ideal vacation?
  76. What superpowers did you wish you had when you were a kid?
  77. Are you a mountain or a beach person?
  78. What mythical animal do you resonate with, and why?
  79. Which member of your family do you feel closest to, and why?
  80. Who do you consider your best friend in your workplace?
  81. What three adjectives would describe you?
  82. If you could live anywhere in the world, where would you choose?
  83. What are you passionate about in life?
  84. What quality in a person do you fall in love with?
  85. Have you had your heart broken before?
  86. What is your take on astrology?
  87. What is your life’s soundtrack? Or what type of music inspires you?
  88. When was the last time you spoke with a classmate from high school?
  89. Are you left- or right-handed, and would you want to switch?
  90. What subject were you good at in high school?
  91. What was the most memorable experience you had in elementary school?
  92. Do you find it difficult to admit that you are wrong, and why?
  93. Do you get excited or scared when meeting new people?
  94. What is your secret hobby that others would consider weird?
  95. How do you cope with stressful situations?
  96. Is there anything that you would like to change about yourself?
  97. What musical instrument do you know how to play?
  98. Who or what inspires you?
  99. Which would you prefer in a romantic partner: a dreamer or an achiever?
  100. What is your favorite part of a house, and why?
  101. Who is the fictional character who closely resembles you in terms of attitude?
  102. When you were a kid, what did you say you wanted to be when you grew up?
  103. What was the title of the first movie you watched in a movie theater?
  104. When was the last time you slept outdoors?
  105. What’s your favorite cheesy pick-up line? Have you ever used it in real life?
  106. What’s your favorite Disney movie?
  107. What is the weirdest scar you have and how did you get it?
  108. Where did you and your best friend meet?
  109. Which of your accomplishments are you most proud of?
  110. What’s the weirdest Wikipedia rabbit hole you’ve stumbled down?
  111. Tell me about the best vacation you’ve ever taken.
  112. What’s your favorite physical attribute about yourself?
  113. Friday night—would you rather stay in or go out?
  114. Do you believe in ghosts?
  115. What piece of art (book, music, movie, etc.) most influenced the person you are today?
  116. Which would be harder for you to give up: coffee or alcohol?
  117. What’s the single best piece of advice you ever received?
  118. Who’s your best friend, and what do you love about him or her?
  119. What’s the greatest risk you’ve ever taken?
  120. If you had 24 hours to do whatever you wanted in this city, what would you do?
  121. What do you like about where you work?
  122. Can you give me an example of how I would collaborate with my manager or supervisor?
  123. Why is this position open right now?
  124. How long has this position been open?good questions to ask 4
  125. How many people have held this job in the last two years?
  126. How long does someone typically stay in this job?
  127. What avenues are available within the company directly after this position?
  128. What can you tell me about the position that isn’t in the job description?
  129. What would be my #1 priority coming into this role?
  130. Can you show me examples of projects I would be working on?
  131. What are the most important skills to have to do well in this job?
  132. When and how is feedback given to me as an employee?
  133. How will I be trained?
  134. Will I have a mentor?
  135. Will I be leading or managing anyone? Can you tell me about their strengths and weaknesses?
  136. What is the last person who had this job doing right now?
  137. Where have successful employees in this position progressed to?
  138. What is the process for formal performance reviews- how often are they conducted and who contributes to them?
  139. Has anyone failed in this position, and why?
  140. How will you judge my success? What will need to happen in the first six months for me to know I have met your expectations?
  141. With whom will I be working most closely or most often in this job?
  142. How does upper management view the role and importance of this position?
  143. Looking at the other people who have been in this role, what are one or two things that set the very top performers apart from the good or average performers?
  144. What have you identified as the most important things to find in a candidate?
  145. What can you tell me about the 6-12 month outlook of this position and where you see it going?
  146. What tasks are really going to define success in this position?
  147. How would I know if I’m succeeding or not month to month?
  148. What’s the toughest part of the job?
  149. Will the work be similar most days, or will there be variety from day to day?
  150. What will the typical day look like?
  151. Do you expect the main responsibilities for this role to change in the next six months to one year?
  152. What improvements or changes do you hope that a new candidate will bring to this position?
  153. What do you think are the most rewarding or gratifying aspects of working in this position?good questions to ask 5
  154. What personality traits would help someone perform well in this role?
  155. Would you like me to do anything differently than the previous people who have held this job? If so, what?
  156. What about my background interested you for this position?
  157. What are a couple of things I could do to quickly become a top contributor in the organization?
  158. How much of an opportunity will I have for decision-making when I start this role?
  159. How much interaction with clients or customers will I have?
  160. What types of strategic decisions will I be able to make immediately without getting approval from my manager?
  161. Will I have the opportunity to work with any cutting-edge tools, technologies or methods?
  162. What advice would you give your 13-year-old self?
  163. What advice would you give your 5-year-old self?
  164. What’s the best advice you could give your future children?
  165. What was the best concert you’ve ever been to?
  166. What’s your favorite vacation spot?
  167. If you could teach any subject in school what would it be?
  168. What is one song that always makes you dance?
  169. What is the one word you use too much?
  170. Of you could sing a duet with someone who would it be?
  171. What’s the best gift you’ve ever received?
  172. What was the biggest plot twist of all time?
  173. If your life was a reality show, what would the premise be?
  174. What innocent food do you despise?
  175. What weird food do you love?
  176. What is your favorite odd food pairing?
  177. What is the stupidest cliche expression right now?
  178. What is a useless topic you know a lot about?
  179. What is the worst backhanded compliment?
  180. Do you have any “that would only happen in the movies” moments?
  181. What common expression is total B.S.?
  182. What is the grossest smell?
  183. What critically panned movie do you love?
  184. What critically acclaimed movie do you hate?
  185. What one person did you have on your wall in high-school?
  186. What’s a movie that made you cry from laughter?
  187. What’s a movie that made you cry from sadness?
  188. Which celebrity would make you the most starstruck?
  189. What’s your favorite app?
  190. What’s your least favorite condiment?
  191. What is the worst fashion trend of all time?
  192. What book have you read the most times?
  193. Would you rather travel 100 years in the past or 100 years in the future?
  194. What is something you always travel with?
  195. Do you ever think it’s OK for a waiter to spit in someone’s food?
  196. What actor would you cast to play you in a movie?
  197. What’s the sexiest animal in the animal kingdom?good questions to ask 6
  198. What app do you check the most?
  199. What is the luckiest thing to ever happen to you?
  200. What is the unluckiest thing to ever happen to you?
  201. What foreign accent can you do really well?
  202. What’s the last book you didn’t finish?
  203. Whats the first app you open in the morning?
  204. What’s something that you don’t know that you want to learn?
  205. Which language do you wish you were fluent in?
  206. What’s a food trend you hate?
  207. Who was your childhood crush?
  208. What was your AOL screen name?
  209. What is your most overused emoji?
  210. How would you spend your remaining time if you found out you only had 10 days left to live?
  211. What’s one item you’ve recently crossed off your bucket list?
  212. Do you have a favorite place in the world, and where is it?
  213. Are you a cat or a dog person, and why?
  214. Are you more afraid of failure or success, and why?
  215. What was your most memorable birthday?
  216. At what age did you have your first pet, and what was it?
  217. What things or situations make you feel unsure about yourself?
  218. What do you feel is your greatest accomplishment to date?
  219. What would you do for the people you love?
  220. At this point in your life, what is it that you wish your family knew about you?
  221. When was the last time you said “I love you” to someone?
  222. If you have to lay your life on the line for someone, who would that person be?
  223. Do you believe in fate, or do you think that things happen because of our decisions?
  224. What period of history would you change if given the chance?
  225. Who is your real-life hero?
  226. What was it like growing up in your hometown?
  227. If you were to give up one of your senses, what would it be?What was your most embarrassing experience at work?
  228. Are you a leftie or right-handed, and would you be willing to switch?
  229. How would people close to you describe you in three words?
  230. What skill do you envy in other people?
  231. What is your pet peeve in the workplace?
  232. What is your view about monogamy?
  233. What was your favorite bedtime story as a kid?
  234. What was your high school experience like?
  235. What clothing fads did you love as a kid?
  236. Did you like school?good questions to ask 7
  237. Did you and your friends like to hang out anywhere special as a teenager?
  238. Do you remember your first date?
  239. Describe your wedding ceremony.
  240. What was an unusual thing your children did when they were very small?
  241. What historical moment stands out most in your memory?
  242. What did you find most difficult about growing up?
  243. Were your parents strict or lenient?
  244. Do you remember your grandparents or great-grandparents? What were they like?
  245. Have you ever been in a serious accident?
  246. Name a good friend you’ve known the longest. How many years have you been friends?
  247. If you could change one thing about your life, what would it be?
  248. As a force, are we humans creative or destructive?
  249. Why do you think people believe in conspiracy theories?
  250. How would you describe honor?
  251. What is the value of art in society?
  252. Can the world really achieve lasting peace?
  253. Do you think that some lives are more precious than others?
  254. What is the perfect life for you?
  255. Do you believe that the day will come when computers will be more intelligent than humans?
  256. What is your definition of fame?
  257. Do you wish to be famous?
  258. What would you want to be famous for?
  259. What is the greatest invention of this age?
  260. Would you be willing to go the extra mile for something or someone?
  261. Which one wins: reality or imagination?
  262. When was the last time you said “I love you” to your parents?
  263. Who do you look up to in life?
  264. Do you give advice to others, and why?
  265. Which is the better option: being a heartbreaker or being heartbroken?
  266. If you could swap lives with someone for a day, who would you choose and why?
  267. Which emotion best represents you, and why?
  268. What do you think will bring about humanity’s extinction?
  269. Do you feel happy when you use social media?
  270. Will you encourage the younger generation to use social media?
  271. How would I describe the perfect day?
  272. What am I willing to go the extra mile for?
  273. What are my top five negative habits that I must change to something better?
  274. Who do I look up to?
  275. What outstanding qualities should my best friend have?
  276. When was the last time I told someone I love him/her?
  277. Am I satisfied with the quality of my romantic relationship?
  278. When have I compromised my personal beliefs because I was afraid to be left out?
  279. What skill do I possess that I can do better than others?
  280. How often have I said yes when I wanted to say no?
  281. What important lesson have I learned this week?
  282. What three words would my friends use to describe me to strangers?
  283. Have I intentionally broken someone’s heart?
  284. Do I really listen when people talk to me?
  285. What surprised me about myself this week?
  286. How many hours have I been spending on the Internet?
  287. Do I engage in negative self-talk?
  288. Am I living a simple or complicated life?
  289. How can I simplify my life?
  290. Are there things that I should have done when I was younger that I can no longer do now?
  291. Who among the people I know bring out the best in me?good questions to ask 8
  292. Do I often make excuses?
  293. What would I ask for if one of my wishes would come true?
  294. Have I matured because of challenges or because of the enjoyable moments in my life?
  295. Would I ever choose the easy way in life?
  296. What’s standing between me and my greatest dream?
  297. Where will I be five in years?
  298. When was the last time I was furious?
  299. What can I do to make a difference in people’s lives?
  300. If failures are the best teachers, why is it so bad to fail?
  301. Is it wrong to steal in order to feed a starving child?
  302. What should I spend more time doing?
  303. What’s the best lesson you’ve learned from a work of fiction?
  304. What food do you crave most often?
  305. Who in your life has the best / worst luck?
  306. What fashion trend makes you cringe or laugh every time you see it?
  307. What’s your best story of you or someone else trying to be sneaky and failing miserably?
  308. Which apocalyptic dystopia do you think is most likely?
  309. If you had a HUD that showed three stats about any person you looked at, what three stats would you want it to show?
  310. What’s the funniest thing you’ve seen a kid do?
  311. What’s your secret talent?
  312. What’s the best way you or someone you know has gotten out of a ticket / trouble with the law?
  313. Tear gas makes people cry and laughing gas makes people giggle, what other kinds of gases do you wish existed?
  314. What’s the most beautiful beach you’ve been to?
  315. What’s the most anxiety inducing thing you do on a regular basis?
  316. What’s something that everyone agrees we should change, but somehow it never changes?
  317. What trend are you tired of?
  318. What’s incredibly cheap and you would pay way more for?
  319. What’s your grossest bug story?
  320. What would the adult version of an ice-cream truck sell and what song would it play?
  321. What company do you despise?
  322. When was the most inappropriate time you busted out in laughter?
  323. What would be an accurate tag line for each month?
  324. What’s the most overrated product out on the market?
  325. What word do you always misspell?
  326. What naps are the most satisfying?
  327. What’s the weirdest thing you’ve found lying on the ground / side of the road?
  328. What’s the funniest TV show you’ve ever seen?
  329. What’s the most embarrassing story from your childhood?
  330. What animal is the most majestic?
  331. What’s something that everyone knows is true, but we don’t like to admit it?
  332. What’s the weirdest text or email you’ve gotten?
  333. What always cheers you up when you think about it?
  334. What sport could you play the longest in a televised game, without anyone discovering you aren’t a professional athlete?
  335. If you could talk to animals and they would understand you, but you couldn’t understand them, what would you do with that power?
  336. What’s the most boring sport, and what would you do to make it more exciting?
  337. What’s the creepiest tech out there?
  338. Who did you use to look up to, but they screwed up and you lost faith in them?
  339. What’s fine in small numbers but terrifying in large numbers?
  340. Do you like things to be carefully planned or do you prefer to just go with the flow?
  341. What animal would you most like to eat?
  342. What fictional characters have you had a crush on over the years?
  343. What would the box with all your hopes and dreams inside look like?
  344. What was the worst shopping experience you’ve ever had?
  345. What story you’ve heard has stayed with you and always disturbs you every time you think about it?
  346. What was the most important appointment or deadline you missed?
  347. If you were a clown themed super hero, what powers would you have?
  348. If you could airdrop anything you want, worth two million dollars or less, anywhere you want, what would you airdrop and where would you airdrop it?
  349. If you lived in a virtual reality world of your own creation, what would it look like?
  350. What escalated very quickly?
  351. What two things are terrible when separate but great when you put them together?
  352. What did you believe for way too long as a child?
  353. What big event do you think will happen soon that most people aren’t expecting?
  354. What still makes you cringe when you think back on it?
  355. What current trend makes no sense to you?
  356. If you owned a restaurant, what kind of food would it serve?
  357. Which celebrity is the most likely to have a collection of canes that are just for show?
  358. What’s the weirdest crush you’ve had?
  359. What do a lot of people have very strong opinions about, even though they know very little about it?
  360. What’s your go to casino game?
  361. An epic feast is held in your honor, what’s on the table?
  362. What’s your favorite holiday movie?
  363. Who is the most manipulative person you’ve ever met?
  364. Who is the most creative person you know?
  365. What’s the funniest pick up line you’ve heard?
  366. What seemingly innocent question makes you think “It’s a trap!”?
  367. How ambitious are you?
  368. What’s the oldest thing you own?
  369. What has someone borrowed but never given back?
  370. Where is the best place you’ve been for taking walks?
  371. If cartoon physics suddenly replaced real physics, what are some things you would want to try?
  372. What from the present will withstand the test of time?
  373. Who in your life is the worst at using technology?
  374. What’s the weirdest conversation you’ve eavesdropped on?
  375. What just around the corner tech are you eager to get your hands on?
  376. What was the darkest movie you’ve ever seen?
  377. What do you do when you hear something fall in the middle of the night while you are in bed?
  378. What outfit could you put together from clothes you own to get the most laughs?
  379. What’s the most disgusting sounding word in the English language?
  380. What was ruined because it became popular?
  381. What outdated slang do you use on a regular basis?
  382. What was the biggest realization you had about yourself?
  383. What’s your best example of easy come, easy go?
  384. What small change greatly improves a person’s appearance?
  385. What topic could you spend hours talking about?
  386. What happens regularly that would horrify a person from 100 years ago?
  387. What do a lot of people hope will happen but is just not going to happen?
  388. What’s the weirdest thing that has happened to you while working at your job?
  389. What questions would you like to ask a time traveler from 200 years in the future?
  390. Which way should toilet paper hang, over or under?
  391. What’s the most physically painful thing you’ve ever experienced?
  392. What horror story do you have from a job you’ve had?
  393. What’s the most rage inducing game you’ve ever played?
  394. What’s the biggest overreaction you’ve ever seen?
  395. What are some of the most common misconceptions?
  396. What job doesn’t exist now but will exist in the future?
  397. What’s the most recent show you’ve binge watched?
  398. What’s the worst movie trope?
  399. What’s a common experience for many people that you’ve never experienced?
  400. What are some misconceptions about your hobby?
  401. What’s the smartest thing you’ve seen an animal do?
  402. What’s the most annoying noise?
  403. What’s your haunted house story?
  404. What did you Google last?

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