401 Deep Questions To Ask (To Get To Know Someone Better)

401 Thoughtful and Deep Questions To Ask

deep questions to ask

I believe that life comes down to the questions that we ask, or DON’T ask. The better the question, the better the potential answers from the other person or people.

Ask your boss for a raise or ask your boss for the certain amount you want. Both will get you your desired outcome of getting a raise. But the second one will result in you making that certain number a month or year more that you truly want.

You are left feeling fulfilled simply by asking the question. And if the outcome happens, your new life resonates with the question you asked.  Which our true questions, I believe, come deep from within our soul. They resonate with our soul. And hence, they connect with other people’s souls. Transcending the physical plane and connecting with people at a spiritual level.

This is where, I believe, is where true growth, happiness and fulfillment lye. When we can communicate at this level, the physical plane manifests itself in a way that we truly desire.

And this all starts with asking the right questions.

As far as deep questions to ask. You may be wondering what good ones are to ask to really allow you to get to know someone. Or even yourself.

Well below, I have done all I can to provide you with the deepest questions to ask. So you can get the most quality answers.

It will help you skip over surface level communication and become a deep diver. Both with yourself. Allowing you to “Know thyself”. As well as get to deeply know anyone you want to know deeply and completely.

Enjoy, my friend.

(DONT MISS! 75 Questions To Ask Yourself For Massive Personal Growth)

401 Deep Questions To Ask

  1. Why do you feel that you are here on this earth?
  2. What is your life’s purpose?
  3. Do you believe in fate?
  4. Do you feel that everything happens for a reason?
  5. If you were to die today, what would be your regrets?
  6. If you were to die today, what would be your greatest accomplishments that you are most proud of?
  7. Do you believe in love at first sight?
  8. What would people tell me your best qualities are?
  9. What does love mean to you?
  10. Do you think life flashes before your eyes when you die?
  11. What kind of legacy do you want to leave behind when you die?
  12. What do you think happens when you die?
  13. What is one thing you can’t imagine living without?
  14. Do you think death will hurt?
  15. Who would you lay down your life for?
  16. Do you believe in enlightenment?
  17. What skills do you wish you had?
  18. Have you ever stayed in a relationship too long? Why did you do so?
  19. What do you feel is your life purpose at this point of your life?
  20. Are you truly happy? If not, what would it take to make you truly happy?
  21. If there is no God, what will that mean to you?
  22. Do you think you are the mind with a body, or a body with a mind?
  23. If there is a God, what would that mean to you?
  24. What was your biggest defining child or adolescent moment?
  25. What if God isn’t what you thought him or her to be?
  26. Do you believe in reincarnation?
  27. What is your definition of happiness?
  28. How were you raised?
  29. Who you you most close to, you father or mother?
  30. Is there a true meaning for life?
  31. Do you think we are all connected in some way?
  32. When was a time in your life where you surpassed what you thought were your physical, mental or emotional limits?
  33. Do you lead with your head or heart more?
  34. Who would be the person you would call if you went to jail and only got one call?
  35. If you could instantly learn a new language, what would it be?
  36. What is a deal breaker for you in a relationship?
  37. How do we know if this life is simply but a dream?
  38. If you could switch places or be someone else for a day, who would it be?
  39. What is the biggest obstacle that you are trying to overcome at the moment?
  40. What if you lived your life and got to the end of it and realized it was a lie?
  41. What is your deepest, darkest secrets?
  42. How do you react during confrontation?
  43. What message would you put on a billboard that would be seen by millions of people?
  44. If you were going to get a tattoo, what would it be and why?
  45. If you could meet anyone, dead or alive, who would it be?
  46. What area of life has you mastered the most or feel most competent in?
  47. If you had the chance to go back and change one thing, what would it be?
  48. What kind of mother/father do you think you will be?
  49. What is your biggest fear?
  50. If you had a couple hours extra a day given to you, how would you use them?
  51. How do you like to be comforted when you become upset?
  52. Do you believe in telepathy?
  53. If you were offered the chance to live life without any suffering at all, would you do so?
  54. What is your spirit animal? Or if you could be any animal, what would it be?
  55. What are the lessons that your intimate relationships have taught you?
  56. Do you feel that dreams have meanings?
  57. What is the nicest thing you have done for anyone?
  58. What is the nicest thing someone has done for you?
  59. If you were to pick the place you could die, where would that be?
  60. If you could go back into the past, what is one decision you would change?
  61. What is the biggest decision you made that resulted in the most positive change in your life?
  62. How do you best connect with other people?
  63. What type of non-profit would you start and why?
  64. What is your favorite family tradition?
  65. What one piece of advice do you think every young person on this earth needs to know?
  66. What was the most important event to you in all of the human race?
  67. What is your favorite memory with your family?
  68. Do you see yourself as being an introvert or extrovert?
  69. How powerful do you think the power of your mind really is?
  70. What words do you want to say on your deathbed?
  71. If you had to describe yourself in one word, what would it be?
  72. If you ruled the world, what would be the first thing you would do?
  73. What was the most life changing book you ever read?
  74. Why do you think we are here or why do you think God created us?
  75. Do you believe in Hell?
  76. What is your most and least favorite quality about each parent?
  77. If you had a say in being born, would you still come to this earth?
  78. What would be your last meal on this earth?
  79. Do you believe in giving people second chances?
  80. Do you keep a journal? If so, how does it make you feel when you write in it?
  81. Do you think that time is real or just an illusion?
  82. Do you believe in karma?
  83. What is the biggest lie you have ever told?
  84. What is your favorite physical body part or attribute about the opposite sex?
  85. Do you believe in parallel universes?
  86. What is your favorite source of inspiration and motivation?
  87. Do you feel like you are paying off karma in this life for the last?
  88. What are your top 5 bucket list items?
  89. Do you fall in love easily or does it take you time?
  90. What is your favorite thing to do in this life?
  91. What is your favorite sport and why is it your favorite?
  92. What is one thing you would change about me? And why?
  93. Who in life are you must jealous of?
  94. Do you believe the best things in life are free?
  95. When was a time you didn’t trust your gut instinct and it ended up not working out?
  96. What does forgiveness mean to you?
  97. What one quality about someone makes you trust them immediately?
  98. What do you people judge about you that is not true at all?
  99. Do you think we are the masters of our own fate and that we create our own lives with our thoughts?
  100. Who is one person you can talk to and confide in about anything?
  101. Are you more black and white in your thinking or do you color between the lines?
  102. What did you want to be when you were growing up?
  103. Are you happy with your life and how it is right now?
  104. What makes you fall in love?
  105. Tell me about the first time you feel in love if you have?
  106. What color of clothing makes you feel totally at ease in your body?
  107. If you could only do one thing for the rest of your life, what would that one thing be?
  108. What can you learn from your parents that you would do differently with your children?
  109. When is the last time you cried and what were you crying about? Did crying make you feel better?
  110. What is your favorite movie line and why?
  111. When could you justify breaking the law?
  112. What makes someone a winner in life?
  113. How do you think other people see you when they first meet you or just in general?
  114. What are you most resentful about your childhood?
  115. What is your favorite childhood memory?
  116. Who was the one person that has believed in your most in your life?
  117. What holiday means the most to you, and why?
  118. If you could solve one major world problem or issue, what would that be?
  119. What does success mean to you?
  120. What is your favorite human quality or emotion?
  121. What fictional place would you like to go to if you cold?
  122. What do you think about more often than anything else?
  123. How will you know when you have become a success?
  124. Do you emphasize material wealth or spiritual wealth?
  125. If you could go and witness any past event, what would you choose?
  126. What was your favorite age to be?
  127. What was the worst year of your life and why? And what did you learn from it?
  128. What do you feel most guilty about in life?
  129. What age are you most looking forward to?
  130. Where would you go if you could travel somewhere for a year?
  131. How do you think you will die?
  132. Would you rather love or be loved?
  133. What do you want to leave behind for your family when you die?
  134. What is your biggest spiritual experience that you have had?
  135. Where do you see yourself in 10 years?
  136. What subjects are the school system missing for success and happiness and why do you think this?
  137. If you were stranded on an island and could pick one person to be stuck with, who would it be?
  138. Who was that one person for you, the white buffalo in a sense? That person who will always be in your heart?
  139. Do you feel like the glass is half full or half empty?
  140. What song has made the most impact on you in this life?
  141. What movie has moved you the most in this life?
  142. Have you ever had any recurring dreams?
  143. Are you afraid of getting old? If so what are these fears?
  144. If you were to write a movie or book, what would it be about? And why?
  145. Are you currently living your passion? If not, what is stopping you from doing so?
  146. What do you think of the current state of the economy?
  147. What does the world WISDOM mean to you?
  148. What is your favorite past time?
  149. Do you believe the rich get richer and the poor get poorer? And why?
  150. What is one thing you always tend to procrastinate on?
  151. What was your favorite subject in school and why?
  152. Who is your best friend and why are they your best friend? What are your favorite qualities about them?
  153. What makes you feel loved?
  154. What is the one thing in life that you cannot believe you did but would never take it back?
  155. Do you put emphasis on saving money or blowing it?
  156. Do you fear death more or never truly living more?
  157. What do you value most in your friendships?
  158. Who are the people who would bail you out of jail in another country? (People that have your back)
  159. How would you sum up your philosophy about life?
  160. Do you think you would get into Heaven if it is real?
  161. What is the best thing that has happened to you this month, this year and this last decade?
  162. Did you want to be more like your mom or dad growing up?
  163. What does true freedom look like to you?
  164. What was your longest and shortest relationship?
  165. What did you love to do as a child?
  166. Do you believe in soul mates?
  167. What is your relationship with religion? What do you like and dislike about it?
  168. What one emotion do you suppress?
  169. What is your favorite sense you like to use most?
  170. What decade would you have rather grown up in or had been an adult in?
  171. What is your definition of the word “service” and how do you contribute to this world?
  172. What does unconditional love mean to you?
  173. Who has shown you the truest form of unconditional love? And what was that act or acts?
  174. What do you do to recharge?
  175. What is your ongoing strategy for growth and personal development?
  176. What does sex mean to you?
  177. What do you feel that your life work is?
  178. What would you do if your parents didn’t approve of your partner? How would you handle it?
  179. What is the first thing you do when you wake up?
  180. How do you feel that you are making this world a better place?
  181. Who do you think has made the greatest impact in this world? Dead or alive.
  182. Do you think you KNOW when you are dead?
  183. Do you believe in spirits?
  184. When was a time when someone took advantage of you? How did that make you feel?
  185. What was your favorite birthday to celebrate and what did you do?
  186. When was a time where you felt completely hopeless?
  187. When was a time for you that you thought you were beat? Or that you hit rock bottom and never thought you would come back from it?
  188. How did you come back from rock bottom? What did you do? Who helped you?
  189. Who is the person that you need to forgive the most?
  190. Who is the person of whom you want them to forgive you? And why do you desire their forgiveness?
  191. What are you most thankful for in your life?
  192. What one job were you terrible at and how did that make you feel?
  193. What is your take on best friends who are of the opposite sex?
  194. Do you believe in yourself? What would help you believe even more in yourself?
  195. What makes you feel most vulnerable?
  196. Have you ever struggled with addiction? And why do you think you used this vice?
  197. Do you believe in life on other planets?
  198. What is one thing or person in this life that you would die for
  199. Has anyone close to you passed away? How did that affect you?
  200. Have you almost died before?
  201. What one thing do you take for granted the most?
  202. What is your definition of true evil? And what is the solution for eradicating it?
  203. What is the happiest moment of your life?
  204. If you had to march for one cause, what would that be?
  205. When have you been humbled in life?
  206. When were you the most scared in life?
  207. What has been your turning point in life?
  208. Where do you think people/souls were before they were born?
  209. Have you ever wanted to not live anymore? Why do you think you felt this way?
  210. When and where and with whom did you go on your first date with?
  211. What are your top 5 core values?
  212. What behavior do you not tolerate?
  213. What is your favorite quality about yourself?
  214. What would you change about yourself?
  215. Who is your current role model?
  216. What song gets you the most pumped up?
  217. Who was your child role model?
  218. Do you consider yourself to have had a good childhood?
  219. What is your relationship with failure?
  220. What action is completely unforgivable to you?
  221. What do you look for in a life partner?
  222. What do you think is the most important historical event.
  223. What helps you relax the most?
  224. What are your pet peeves?
  225. Do you feel that the loved ones that have passed on are reaching out to you in some way or can talk to you?
  226. What friends father or mother did you admire most growing up? And why did you admire this person so much?
  227. What were your first thoughts when we met?
  228. What is one thing in life that overwhelmes you?
  229. Would you choose too be rich or deeply in love?
  230. What qualities do you want written on your tombstone or said at during your funeral?
  231. What memory in life makes you smile the biggest?
  232. Do you believe in evolution?
  233. What is your definition of a healthy relationship?
  234. When was the time where someone broke your heart?
  235. Have you ever broke someone’s heart?
  236. What is a good first impression to you?
  237. What is a job you really wanted and applied to but did not get?
  238. What is something that you are good at but is embarrassing?
  239. If there was only one goal you could accomplish out of your current list, what would that be, and why?
  240. Do you believe that your thoughts create your reality?
  241. Who was your favorite president and why?
  242. When did you cut someone out of your life that you knew was not good for you? How hard was it to do so?
  243. What is your perspective on war?
  244. Do you think all people are created equal?
  245. When was a time when you held back your love and regret doing so?
  246. What is your biggest life lesson?
  247. Has God ever talked to you?
  248. What has been your favorite and least favorite nickname given to you?
  249. What would be one superpower that you would choose?
  250. Who is the hardest worker you know?
  251. Do you believe in astrology?
  252. What is a major turnoff for you in a relationship?
  253. If you could have one quality or skill bestowed upon you, what would that be?
  254. Do you think the world will ever truly end? If so, how?
  255. Do you believe that you are here for a purpose or is it all an accident?
  256. If you were financially free, what would you do with your time?
  257. If there is one organization you could give a million dollars to, what would it be?
  258. Do you remain friends with your exes?
  259. Have you ever seen something you can’t quite explain?
  260. Have you ever questioned your sanity?
  261. If you could know the day, hour and minute you were going to die, would you want to know it?
  262. Would you rather explore outer space or the ocean?
  263. What is the one thing you want to instill in your children?
  264. What has been the most adventurous event that you have participated in?
  265. What goal have you given up on or left aside that you want to go back and revisit?
  266. Who do you feel most safe with in your life?
  267. Do you think serial killers are born that way or shaped?
  268. Do you like to hear good news or bad news first?
  269. Why do you think mental health issues are so rampant nowadays?
  270. How could the government help improve the world?
  271. What is one thing that you struggle with on a daily basis?
  272. Are you where you thought you would be at this point in your life?
  273. When do you think someone is a “grown up”. What age.
  274. Are you into looks or brains?
  275. What you ever take someone back who has cheated on you?
  276. Would you ever like to be famous or have wanted to be famous?
  277. Do you hold grudges? If so, what is one of them?
  278. What is one area of your life where you feel like you cannot get ahead?
  279. If you had the chance to give your problems to your worst enemy, would you do so?
  280. Are you for or against the way the world is heading?
  281. Have you ever stolen? And did you feel guilty about it?
  282. What things in life have made you the way that you are?
  283. What has been your biggest blessing in disguise?
  284. Have you every blamed God for your problems?
  285. Do you think God truly answers all prayers?
  286. So you believe in supernatural spirits?
  287. Do you have a feeling about how you are going to die?
  288. What is one thing you would save out of your house if it were burning down?
  289. What is your biggest current challenge?
  290. How many kids do you want?
  291. If you could punch anyone in the face, who would that person be?
  292. Do you believe in retaliation?
  293. What would you do if you won the lottery?
  294. What was the first thought you had when you met me?
  295. What can I do to make you feel more appreciated?
  296. Do you feel like it is OK to spank your kids?
  297. What turns you on most about someone you are dating?
  298. What is your top romantic memory?
  299. What is your favorite guilty pleasure?
  300. What emotion do you deal with the most in your daily life?
  301. What is your perfect vacation?
  302. If you could have picked your name, what would it have been?
  303. Were you ever picked on or have you ever picked on someone?
  304. What were you like in high school/junior high?
  305. What do you want to do with your retirement years?
  306. What would be the title of your life if it was adapted into a book or movie?
  307. When was a time in your life when you were almost arrested, or were arrested?
  308. Where in the world have you been or where do you go to where you feel most at peace?
  309. What race would you want to be if you could choose one?
  310. When was a time in your life where you wanted to just give up? And what was going on that made you feel this way?
  311. Do you think your are gullible or more of a skeptic?
  312. How do you handle loss and pain?
  313. What is your perfect morning routine to get you started on the right foot?
  314. What one question for me to ask you would let me get to know you best?
  315. What is your favorite piece of art in the world and why?
  316. What do you look for in a presidential candidate?
  317. If you had the power to make anyone in the world president, who would it be?
  318. What did you learn from your worst relationship?
  319. What did you learn from your best relationship?
  320. Do you think celebrity figures are entitled to be good role models?
  321. When upset, do you preferred to be left alone or given attention?
  322. What is your favorite comfort food?
  323. What one scent puts you at ease or makes you happy?
  324. Do you remain friends with your exes?
  325. What planet would you visit if you cold go to any?
  326. What do you think about when you are alone?
  327. Are you a hopeless romantic?
  328. How do you want people to feel when you are around?
  329. Do you still have feelings for any of your exes?
  330. Who do you like most in your family?
  331. Are you more of a leader or a follower?
  332. What one thing would you change about your childhood?
  333. How would you handle it if you found out you were cheated on?
  334. Do you believe the devil is really there to punish you? Like it is a real person?
  335. Are you a cat or dog person? And why?
  336. Did you ever feel like running away as a child? And why?
  337. Who was your favorite teacher throughout your school career? And why?
  338. Did you feel supported by your parents as a kid?
  339. What is your relationship with your siblings?
  340. Do you think we will ever find a cure to all the major diseases?
  341. Do you get along better with men or women?
  342. What is the best and nicest compliment anyone has every given you?
  343. Do you think people really can change? Or are we just the way we are?
  344. What habit have you formed that you are most proud of?
  345. Do you think your parents are proud of you?
  346. Have you ever done drugs? (No judgement here!)
  347. What keeps you up at night?
  348. What is the worse thing you have ever done?
  349. What do you like most about yourself?
  350. Do you prefer prayer or meditation?
  351. How much emphasis do you put on obtaining power in this life?
  352. Do you feel that psychics and future predictors have a gift? Or is it all BS?
  353. What earns your respect?
  354. What is the best way to resist peer pressure?
  355. What do you like and dislike about technology?
  356. How do you take criticism?
  357. When in your life were you the least secure about yourself?
  358. When in life were you most secure about yourself?
  359. Would you want a boy or girl?
  360. What scared you the most as a child?
  361. What do you hate about the country you live in?
  362. What do you love about the country you live in?
  363. Do you truly think honesty is the best policy?
  364. Are you a democrat or republican and how did you choose?
  365. What is the biggest risk that you have taken in any area of your life?
  366. How long does it take to truly get to know someone?
  367. What is your take on online dating?
  368. How do you confront people who lie to you?
  369. What is your favorite app right now to use and why? Or which one has changed your life the most for the better?
  370. When did you find out that Santa and the Easter Bunny were fake and how did you take this?!
  371. Have you ever struggled with suicidal thoughts?
  372. Did you parents give you tough love or were they enablers?
  373. Do you considers yourself more decisive or indecisive?
  374. What self destructive thing do you most like to engage in?
  375. Do you think there is an actual end to the universe?
  376. How do you define beauty?
  377. What is your take on religious guilt?
  378. What was the worst date you have have been on?
  379. Have you ever cheated on someone?
  380. What makes home feel like home to you?
  381. What advice would you give someone who is just about to graduate high school?
  382. Do you think traditional education or self education is more important?
  383. What name would you have picked if you could have chosen your own name?
  384. If you were told you only had 6 months to live, how would you live it?
  385. Would you rather adopt an animal or buy them from a breeder? And why?
  386. What is the perfect date night for you?
  387. What is your favorite sexual position?
  388. What is the one thing you never want your family to know you did?
  389. If you were to become president one day, who would you want as your vice president?
  390. What one thing is too serious to be joked about?
  391. When did you lose your virginity?
  392. What do you consider to be the best financial investment?
  393. How do you define “cheating on someone”?
  394. How do you want to impact the world?
  395. Who is your favorite celebrity could, and why?
  396. What would be your biggest hope for your future or current children?
  397. Do you believe in the phrase “opposites attract”? Why or why not?
  398. What one thing do you think is holding you back in life?
  399. What is your favorite color and why?
  400. Who is the celebrity or public figure that you absolutely cannot stand?
  401. Are you still friends with people from your childhood?

Conclusion To Deep Questions To Ask To Get To Know Someone

So there we are my friend. 401 deep questions to ask to truly get to know someone. This list can be used to get to know your loved ones, new friends, new potential love interests, and like I said above, even yourself.

Share with me what you thought about this list. What questions it may be missing that we can add to help ask more deep questions. As well as what your favorite question was!

Let’s chat in the comment section below!




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