Best Deep Questions That Make You Think
While all questions are good to get to know someone or reconnect with friends and family, most of them just scratch the surface of what a person is about. Not these!
After asking these deep questions, you’ll understand how others think, how they prefer to live, and what they find most valuable in life. This is so important to know about the people around you.
Plus, there’s a set of deep questions to ask yourself and dig into your own beliefs hidden under the surface.
Deep Questions to Ask Someone (To Get to Know Them)
First, these deep questions to get to know someone will help you open up, and reveal things that don’t come up in small talk.
1. What is your most cherished possession?
2. What were you like as a kid?
3. Who was your hero growing up and why?
4. What is something exciting that happened to you recently? Why was it exciting?
5. If you could only celebrate one holiday per year, which would it be?
6. How much of an impact does music make on your life?
7. What is one thing you do daily that makes you crazy happy?
8. Of all the places you’ve lived, what has been your favorite place?
9. What is something about you that you don’t tell a lot of people about?
10. Where is your favorite restaurant? What do you order there?
12. What has turned out to be a huge silver lining in your life?
13. When you were a kid, what was your favorite day of the year? Why?
14. What are the 3 best things that have happened to you in the last year?
15. Are you happy with your job?
16. Are you a perfectionist?
17. What if you had to delete all of your social media accounts? Would it be easy or hard?
18. What is one thing you are truly horrible at?
19. What do you enjoy daydreaming about?
20. What is the best compliment you’ve ever received?
21. Do you consider yourself to be health-conscious?
22. Would you rather stay up late playing games or stay up late reading a book?
23. What does your perfect day look like?
24. What is a type of movie you really hate?
25. What’s your favorite season, and why?
26. What’s one song that you will be playing for your kids and/or grandkids someday, no matter how old it makes you seem?
27. Do you consider yourself more religious or more spiritual?
28. Do you think your job will still be around in 50 years? (Why or why not?)
29. What do you admire most about your parents?
30. What’s your favorite book of all time? Why?
31. What’s your favorite movie of all time? Why?
32. When you turn on the television, what do you hope to watch first?
33. What’s the best meal (homecooked or restaurant) you’ve ever had?
34. If you had to change careers, what would you decide to do instead?
35. Are you a dog person or a cat person?
36. Where is the last place you’ve been to? Does it say anything about you?
37. If you have a pet, do you consider it to be an animal, friend, or family member?
38. What’s your favorite hobby? (See great hobbies for women)
40. How are you different from the rest of your family?
41. In your family, who is most likely to take care of your parents when they grow old?
42. Do you consider yourself more of an introvert or extrovert? Why?
43. Do you like working from home or working in the office? Why?
44. Who do you admire, and why?
45. What is your favorite family tradition example? (Today or from your childhood)
46. If you have a big decision to make, who do you talk to about it?
47. Do you love celebrating your birthday or try to ignore it?
48. What meal takes you back to your childhood? What does it remind you of?
49. What types of activities make you anxious?
50. What is one activity that always calms you?
Deep Questions To Ask Friends
Next, these deep questions for friends are wonderful for someone you already know and have a relationship with.
51. How would your closest friends describe you?
52. What one song speaks to your soul?
53. If someone gave you $10,000 out of the blue (no strings attached), what would you do with the money?
54. Do you believe in reincarnation?
55. If you could only pick one person on Earth to trust, who would it be?
56. Do you think discipline is important to a life well lived? And if so, what does that look like?
57. Name a bias you have that you are working to let go of.
58. When was the last time you tried something new?
59. Name one thing most people don’t know about you.
60. What has been your most embarrassing moment?
61. Name three of your happiest moments in life.
62. What helps you best fall asleep at night?
63. Have you ever had recurring dreams (or nightmares) before?
64. What’s one thing you hope to learn how to do someday?
65. What are the values you most want in your friends?
66. What has been the best road trip you’ve ever taken?
68. How do you feel about change? Do you react well to it, or not?
69. Which of your parents are you most like?
70. What is the first thing you think when you wake up?
71. What is the last thing you think about before you fall asleep?
72. Who was your favorite teacher growing up? Why?
73. Do you think having money is important? Why or why not?
74. In your opinion, what should people be doing more of that they don’t?
75. Do you write in a journal? What do you write about?
76. What’s the longest friendship you’ve had? Why do you think it has lasted that long?
77. When was the last time you felt like you didn’t belong somewhere?
78. What is one object you don’t think you could live without?
79. Do you believe in karma?
80. If you could dare your friend into doing something, what would it be?
81. When was the last time you did something on impulse? How did it turn out?
82. What book have you read that you would give to all your friends? Why?
83. What’s one mistake that you learned from and you’ll never make again?
84. If you could be famous for one thing, what would you want it to be?
85. Have you ever questioned your sanity?
86. Are you a political person? What has impacted your political beliefs?
87. What does the perfect vacation sound like to you?
88. What does the perfect weekend sound like to you?
89. Do you prefer to save, spend, or invest?
90. If you could have a coffee with anyone in the world (dead or alive), who would it be?
91. Do you think that, as a society, we’ll destroy the Earth one day?
92. What is one quote that always inspires you?
93. Would you say that you trust people easily? Why or why not?
94. What if you suddenly became world-famous? Would you love it or seek isolation away from the world?
95. Have you ever tried meditation before? What did you think of it?
96. What is one thing you’re grateful that your parents taught you?
97. Are you afraid of anything irrational? Or weird?
98. When was the last time you had a conversation with someone you didn’t know?
99. Are you a morning person or a night owl?
100. If you won the lottery tomorrow, what would you do with all the money?
Deep Questions for Couples
Next, use these deep questions to ask your boyfriend, girlfriend, or spouse. They work well with understanding the person you share your life with. So, reconnect during your next date night!
101. What is your happiest memory of your relationship?
102. If you could get married anywhere in the world, and it could be anything you wanted, what would your dream wedding look like?
103. What is the one thing that draws you most to your partner?
104. What values are most important to you in a partner?
105. How do you like to show your partner love?
106. What is something you need in a relationship? Perhaps more than most. (Ex. touch, honesty, tenderness, etc.)
107. What has been your best kiss? What made it so great?
108. Would you move away to be with your partner?
109. Do you feel as though the tough moments with your partner have brought you closer together? How so?
110. Do you think you had good role models of relationships growing up?
111. Do you think your money should be together or separate as a couple?
112. If you could take your partner anywhere in the world, where would you go together? (And what would be on your couples travel bucket list?)
113. What is your love language?
114. Have you ever cheated on anyone? Or been cheated on?
115. What is your biggest relationship deal-breaker?
116. Have you ever broken someone’s heart? Has your heart ever been broken?
117. When you’re angry, do you prefer to fight or be left alone?
119. What is one thing you could never do for your partner?
120. Where do you like to go when you want to be alone?
121. If you could go on a dream date with your partner, what would it be?
122. Would you let your kids live with you as adults?
123. Do you think guys and girls can truly just be friends?
124. When do you feel the most connected to your partner?
125. When do you feel the least connected to your partner?
Deep Questions About Life
Next, these deep questions make you think hard about our journey on Earth.
126. What’s one risk you took in the last year that paid off?
127. If you could mark one thing off your bucket list tomorrow, what would it be?
128. Who are three people who have had a huge impact on your life? Why?
129. Do you believe everything happens for a reason?
130. What is one life lesson you had to learn the hard way?
131. What do you feel most grateful for in your life?
132. What has been the best time in your life so far? Why do you think that is?
133. If you could have one thing, what would you want more of in your life?
134. If you could subtract one thing, what would you want less of in your life?
135. What has been your greatest obstacle to overcome?
136. What are you most proud of accomplishing in your life?
137. What do you say to yourself when you make a mistake?
138. When you think of “peace” or “calm,” what image pops up in your head?
139. How has your sense of identity changed throughout life? (Do you feel that you are the same person you were 10 years ago?)
140. Are you living how you thought you would be when you were a kid? How so (or not so)?
141. What is your biggest fear?
142. Do you believe more in fate or free will?
143. What is one thing that you feel is deeply wrong with the world today?
144. What is one thing that you think our society has gotten right?
145. Has anyone you were close to passed away?
146. What is the most beautiful thing you’ve ever experienced (or witnessed)?
147. What do you think the purpose of life is?
148. What would you like for your life to look like when you’re 80?
149. How would you like to act when you’re 80?
150. Do you think most people live? Or do most people just exist? What’s the difference?
151. What do you think makes a good leader?
152. When in your life have you felt failure the deepest? Why? And did you learn anything from it?
153. When in your life have you felt the highest success? Why?
154. Which time period do you think is the best time to be alive: 50 years ago, the present, or 50 years in the future?
155. What is the scariest thing you’ve ever been through?
156. What’s your biggest life regret?
157. What do you think happens after a person dies?
158. If you could find out what your future held, would you want to know?
159. What religion do you most identify with? (Judaism, Christianity, Islam, etc.) And what is it about their core beliefs that speak to you?
160. Do you believe that we all have a soul?
161. Do you think people deserve second chances?
162. Do you believe we are alone in our Universe, or that other species exist?
163. Is there ever an okay time to lie?
164. If someone found a way to live forever, would you want to?
165. If you could fix one problem in the world today, what would it be?
167. If you knew you were going to die tomorrow, how would you spend today?
168. What’s one thing that truly seems great about getting older?
169. What has been the hardest day of your life?
170. What is one stereotype people believe when they look at you? And is it true?
171. What does your dream job look like?
172. Is it ever okay to break the law?
173. If you could find out how or when you died, would you want to know?
174. Has there ever been a time in your life when you worked crazy hard, but loved every moment of it?
175. When you die, would you prefer to be buried or cremated? Would you have your ashes spread? Where?
Personal Deep Questions to Ask Yourself
Next, these deep personal questions make you think about if how you’re living your life aligns with your deepest values. This section is fantastic for grabbing your journal and digging into self-discovery.
176. What if you found out you had 6 months to live? What would you do?
177. What do you consider to be your biggest strength?
178. Where do you want to be in 5 years?
179. If you could only leave your children with one piece of advice, what would it be?
180. What does happiness mean to you?
181. What is one thing you would do if you knew you could not fail?
182. What is something that happened yesterday that makes you smile?
183. If you made a dream board today, what sections or examples would be on your vision board?
184. When was the last time the fear of failure stopped you from doing something you knew you should do?
185. When you die, how do you hope you are remembered?
186. What life lesson, was painful, but helped you make a major life decision or shift?
187. Who are the 5 people you spend the most time with?
188. Of these 5 people, are they all loving and positive relationships? (And if not, how can you spend less time with them?)
189. If you could change one habit for the better, what would it be?
190. Name one thing that you did yesterday that you are proud of.
191. When was the last time you did something that scared or challenged you (produced butterflies in your stomach)?
192. What is one thing that makes you jealous? Why do you think that is?
193. What is one thing you dream about doing someday, but you don’t tell anyone about? (And maybe have a hard time admitting to yourself?)
194. Does your work add meaning to your life?
195. If you could only teach your children one value, what would you want it to be?
197. Do you follow your heart or follow your head?
198. If you had a three-day weekend every week, what would you do with your time?
199. When was the last time you forgave someone that you needed to forgive?
200. When was the last time you felt lonely? Why do you think this was?
201. If you could give your younger self one piece of advice, what would it be?
202. What are you holding onto that is keeping you down or keeping you from giving your best?
203. What is one core belief or value that you never want to compromise on?
205. What’s the biggest lie you’ve ever told?
206. What’s one thing you can do today to make someone’s day better?
207. If you thought about your last week, do you think you have a good work-life balance?
208. Consider your thoughts for the day. Did you talk to yourself the way you would a friend?
209. If you were to give yourself a daily mantra, what would it be?
210. When you look at your life from 10 years ago, what do you miss the most?
211. When you look at your life from 10 years ago, what are you relieved is over?
212. What is a quality that you have that you try to make small or tamper down around others?
213. What is the bravest thing you’ve ever done? How did it change you?
214. How do you want people to feel when they’re around you?
215. What is one interesting discovery you’ve made about yourself in the last year?
216. When you die, do you think there’s anything you will regret?
217. If you believe there may be regrets, what could you do today or this week to begin taking action on it?
218. When was the last time you went out of your way to help someone?
219. If you had to record it, how much time in the last 24 hours was spent on your devices?
220. When was the last time you took a day off for your mental health?
221. What is going really well in your life right now?
222. Where do you think you have room to improve in your life right now?
223. What is something that you wish you had started sooner? Why didn’t you?
224. How do you define happiness?
225. How do you define success?
Related Post: Rapid Fire Questions to Ask
Deep Questions to Ask a Girl
Use these deep questions to ask a girl about herself, and help her share hidden aspects of her thoughts and beliefs.
226. What is one quality you appreciate deeply in another person?
227. Would you rather love or be loved?
228. What was the last book you read?
229. When was the last time you put your whole heart into something?
230. What is the hardest thing you’ve ever done?
231. Are you ok with confrontation or do you wish everyone would get along?
232. Can one person truly bring change to the world? How?
233. Do you think it’s important to have big goals for yourself? Why, and how ambitious should they be?
234. What does “beauty” mean to you?
235. Where do you go when you need inspiration?
236. Have you ever done something you regret to fit in with others?
237. If you were to give up something today that would make your life better, what would it be?
238. What’s the worst advice you’ve ever received?
239. If you could have any artwork, from any painter in the world, which would you choose?
240. Do you keep a lot of deep secrets? Does it bother you if you do?
241. If you were to give yourself a self-care day, guilt-free, what would it look like?
242. What’s your favorite hobby?
243. What was the last movie or book that made you cry? Why?
244. What do you love most about your job?
245. Are you happy with the split of responsibilities in your household? (See a great chore list to divide them better here)
246. Who was your celebrity crush as a kid?
247. If you had to be on a reality tv show, but you could choose which one, what would it be?
248. What personal boundaries have you set to make your life happier?
249. What is something that you think should be taught in school, but it’s not?
250. Do you ever suffer from FOMO? How do you handle it?
251. When were you the maddest you’ve ever been? What happened?
252. What’s one big lie people tell themselves so they can feel better?
253. Name one thing that scares you about our world today.
254. Name one thing that warms your heart about the world today.
255. Does rewarding yourself improve your motivation?
256. Are you a people pleaser, or do you not care much about what others think?
258. If you could learn another language, which would it be?
259. Do you listen to your intuition (gut feelings) or are you guided more by logic?
260. Do you believe in the power of prayer?
261. What’s your biggest secret indulgence?
262. Name three things you love about your body.
263. Name three things you love about your mind.
264. When do you feel unstoppable?
265. What makes you different from everyone else?
266. What’s something you did a long time ago that still makes you feel guilty?
267. How do you handle distractions when you are trying to focus on something?
268. What did your family fight about growing up?
269. What is something that you don’t tolerate from other people (no matter who they are to you)?
270. What is one thing you get embarrassed about buying?
271. Would you say you’re stronger than you look? In what ways?
273. Could you go without social media for a week?
274. What tends to give you the most anxiety? What do you do when you feel this?
275. When you think of your main priorities (work, family, etc.), what is the difference between mediocre and extraordinary?
Let’s Get Deep Questions to Ask a Guy
These are fun deep questions to ask a guy you’re talking to. They’ll let you peek into his core beliefs.
276. Do you think you set a good example for others?
277. Who has been the most terrifying person in the history of the world? Why?
278. If you made one small change to be healthier today, what would it be?
279. What’s the best way to start your day?
280. Do you think it’s more important to manage your time, your energy, or your focus?
281. What’s one thing you’ve changed your mind on as you’ve gotten older?
282. Have you ever felt that you made yourself smaller to fit in with the crowd? When?
283. What action (or gift) has someone done for you that you’ll remember for the rest of your life?
284. What’s the craziest thing you’ve ever done?
285. When you hear someone say “stay humble,” what do you think that means?
286. What historical figure do you think is the most interesting? Why?
287. Do you support the people around you? How so?
288. Do you think it’s possible for parallel universes to exist?
289. If you stay on the same path that you are now, what will your life look like when you’re 60?
290. What keeps you up at night?
291. What’s the disease that you hope is cured next?
292. What was the last thing you saw or read that you found motivating?
293. Do you ever compare yourself to someone else?
294. If there was a zombie apocalypse, would you want to die, become a zombie, or spend your life fighting to stay alive?
295. Are you a helpful person? Why or why not?
296. What’s your most embarrassing memory from childhood?
297. What movie do you think would be amazing if it was real?
298. What’s the best vacation you’ve ever taken?
299. Do you believe yourself to be free to live your life how you want to?
300. What is something people say, that you think is horrible advice?
301. What is the weirdest thing you do?
302. What is one object that you can’t live without?
303. Do you consider yourself close with your family?
304. Do you like surprises? Why or why not?
305. What phrase would you put on a billboard if you could?
306. Do you like the age that you are?
307. When you are overwhelmed and looking for an escape, what is your diversion of choice? (Ex. online shopping, video gaming, eating, drinking, working)
308. Do you think the Matrix is real?
309. Do you think that technology improves our lives? Or erodes them?
310. If you could trade places with anyone for a week, who would it be?
311. Could you go without your phone for a day?
312. Would you ever move to a place that had no family or friends?
313. What’s the best way to end a long day?
314. What is your thought process when you have to make a big decision? Who do you talk to?
315. Do you take steps to live a healthy lifestyle? How so?
316. What makes you smile even when you’re having a bad day?
317. What are you passionate about outside of work and family? (Ex. sports, fishing, etc.)
318. Do you think you’re saving enough money for your future?
319. How does your family celebrate major holidays?
320. Would you consider yourself a “family man”? How so?
321. Do you prefer freedom or structure?
322. What do you think makes something “good” art?
323. What makes you feel alive?
324. What is something that people do that gets on your nerves quickly?
325. Do you believe in the law of attraction? (Your thoughts create your reality)
Kids Questions To Make them Think
Finally, don’t forget to get the kids in your life to share their thoughts too.
326. What do you want to be when you grow up?
327. Have you ever been scared of the dark? (Find: funny have I ever questions)
328. What’s your absolute favorite thing to do with your family?
329. If you could trade places with any grownup for a day, who would it be?
330. What’s something that your parents do for you that you really appreciate?
331. What’s the best book you’ve read recently, and why was it so good?
332. When was the last time you showed kindness to someone?
333. What makes you happy?
334. What makes you sad?
335. What makes you angry?
336. What helps you feel better when you are sad or angry?
337. What do you love most about your birthday?
338. What’s one goal you’d like to achieve this year?
339. What makes you the same as your siblings? What makes you different?
340. What makes you the same as your friends? What makes you different?
341. What’s your favorite family tradition for holidays?
342. Do you feel connected to your family? How so?
343. When was the last time you said “I love you” to someone?
345. What three things are you thankful for today? (See kids gratitude activities)
346. What is something you love about a friend you have?
347. Who or what motivates you to do your best?
348. How can you keep going when something is hard and you want to quit?
349. Do you think it’s better to never try something or to be bad at it?
350. What do you wish you had more time to do?
To Consider With Connecting Deeply
These personal questions can be done in many different situations! Try them:
- During date night or family night
- While waiting in line together
- During a road trip or camping trip
- When meeting someone new (and you want to know more than the basics about them)
- Anytime you need to reconnect!
Enjoy the deep questions to ask friends and family and have fun getting to know them on a new level.