Over 200 Deep Questions to Really Get to Know Someone

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Ready to get to know someone on a whole new level? Use these deep questions to spark a conversation that encourages intimacy, openness, and meaningful exchanges.

This could be with someone you’ve been dating for a while. It could be an old friend you’re reconnecting with. Or, push to have conversations like this with someone you’re already close to. You’ll be amazed at what you’ll learn and how open you can both be.

a list of 50 deep questions you could ask someone in three categories with checkboxes to check if you've asked them

To Get to Know Someone

Spark an open and meaningful conversation with someone you’ve just met by using some of these deep questions, and see what you can learn about each other.

1. Which five things are most important to you in life?

2. What would you like people to say about you at your funeral?

3. Have you ever had a near-death experience?

4. If you could live anywhere in the world, where would you choose?

5. Do you think your star sign accurately describes your personality?

6. Do you have any regrets about your life?

7. What experience in your life has pushed you furthest out of your comfort zone?

8. What subject would you love to know more about?

9. What talent or skill do you wish you had? 

10. Do you make decisions with your heart or your head?

11. Which quality do you most value in a person, kindness or honesty?

12. How would you describe your personality in five words or less?

13. What book has impacted you the most?

14. Where would your dream holiday be? 

100+ Deep Questions To Really Get To Know Someone (questions 1-14 listed below).

15. What would you do differently if you weren’t afraid of judgment?

16. Are you ever afraid to be yourself? 

17. What is your proudest non-academic achievement?

18. Do you prefer to be in a big group of friends or spend time with people one-on-one?

19. What has been your most memorable trip, and why?

20. Would you like to become famous? If so, what would you like to be recognized for?

21. Do you tend to forgive easily or hold a grudge?

22. If you could only eat one meal for the rest of your life, what meal would you choose?

23. What does happiness mean to you?

24. Is your glass half empty or half full?

About Life

Really get to understand a person’s experiences and how they view the world by asking each other some of these deep questions about life.

25. Who in your life has influenced you the most?

26. Do you think that dreams can give you an insight into the future?

27. What is your purpose in life? 

28. Do you think things in our life happen for a reason, or it’s all a matter of chance?

29. Do you think there is a meaning to life? If so, what is it?

30. Do you think you can enjoy good experiences if you’ve never had any bad experiences to compare them to?

31. What one piece of life advice would you give to your 16-year-old self?

32. Do you think it’s possible to always live in the moment?

33. Do you think people prioritize money and possessions more than they should? 

34. What life lesson did you learn the hard way?

35. What quote do you live your life by?

36. If you knew you would die in 10 years, how would you spend the rest of your life?

About Love and Relationships

Connect on an intimate level with these deep questions about love and relationships, particularly if you’re connecting with someone and want to know if there could be a future between you.

37. Have you ever been in love? 

38. What physical feature tends to first attract you to a romantic partner?

39. What values are most important to you in a potential partner?

40. How would you define love?

41. When was the first time you said ‘I love you’ to somebody who wasn’t a family member?

42. Do you have a fear of commitment?

43. Do you believe everybody has a soul mate?

44. What’s the most romantic thing you’ve ever done for somebody?

45. What’s the most romantic thing anybody has done for you?

46. Have you ever had your heart broken? 

47. What would your dream date consist of?

48. What is a dealbreaker for you in a relationship?

49. What’s the most important lesson you’ve learned from a previous relationship?

50. Do you believe it’s possible to stay friends with an ex-partner?

51. What is one thing a potential partner should know about you?

52. Do you think marriage still has an essential place in today’s society?

53. What’s the best way for somebody to show you that they love you?

54. Have you ever been in unrequited love with somebody, or has somebody ever been in unrequited love with you?

About the Future

No one truly knows what will happen in the future, but these deep questions can help spark intriguing conversations about what you both think may or may not happen.

a list of 50 additional deep questions you could ask someone in three categories with checkboxes to check if you've asked them

55. Do you think that robots will eventually take over human jobs?

56. How do you think humans will combat the climate crisis?

57. Do you think AI will help or hinder humanity?

58. Do you think robots will ever be truly sentient?

59. If humans continue to evolve, what physical features do you think we will develop next?

60. What’s on your bucket list for the future?

61. What do you see your life looking like in 10 years?

62. Do you worry about not achieving everything you want to accomplish before retiring?

63. If a crystal ball could show you a particular year from your future, which year would you choose?

64. If you could move to another habitable planet in the future, would you go?

65. Do you think we will ever eradicate poverty? 

66. What’s your biggest fear about the future?

67. What do you think will be the most significant invention that humanity will create in the next ten years?

68. Which parts of the world do you most want to visit in the future?

69. If robots and AI develop consciousness, should they be given human rights?

About Careers & Professional Goals

Understand where someone is at, and where they wish to go, on a professional level with these career and goals questions.

70. Do you work to live or live to work?

71. Are you more motivated by money or personal development?

72. Do you work better under pressure or in a calm environment? 

73. Where do you see yourself professionally in 5 years?

74. What is one thing you would love to have achieved by the end of your career?

75. Which job that you’ve had has taught you the most?

76. Which colleague or manager has had the most significant impact on your professional development?

77. What job would you most like to do if money was no object?

78. Which successful businessperson do you most look up to?

79. If you could ask your professional hero one question, what question would you ask?

80. How do you deal with professional setbacks?

81. Do you currently have your dream job? If not, what is holding you back from getting it?

82. What’s the best and worst thing about your current (or most recent) job?

83. What do you think makes a great manager? What makes a bad manager?

84. Have you ever failed at something? If so, what did it teach you?

85. Do you think people can successfully date a co-worker?

86. What would you change about the world of work?

87. Do you think people are more or less productive when working from home?

88. Do you think the job you’re currently doing (or have done most recently) accurately reflects your skillset?

89. Would your teenage self be surprised at your career choices?

90. Would you take the job of your dreams if it meant moving across the world?

About Personal Beliefs

From views of the world to spirituality, these deep questions about personal beliefs will allow you to connect on an intimate level about life and its purpose.

91. Do you hold any religious or spiritual beliefs?

92. What are the most important values you’d want a potential friend or romantic partner to uphold?

93. Do you support a particular political party? 

94. Do you believe in an afterlife?

95. Do you believe in ghosts or spirits?

96. Do you think that life exists on other planets?

97. How many of your personal beliefs come from your family?

98. Do you believe that a relationship can survive long-term without monogamy?

99. Which current social issues are most important to you?

100. What belief did you used to hold that you’ve since changed your mind on? 

101. What’s your most controversial opinion?

102. Do you believe in karma?

103. Do you think we have a moral obligation to help those less fortunate than us?

104. Do you think humans have been reincarnated, or is this our first time existing?

105. Are environmental issues important to you?

About the World

Great for learning and discussing everything from politics to the world’s biggest challenges, these deep questions can bring about hours of healthy debate and intriguing conversation.

a list of 44 additional deep questions you could ask someone in three categories with checkboxes to check if you've asked them

106. What do you think are the most significant issues facing humanity today? If you were in charge, how would you solve them?

107. Do you think social media is a force for good or evil in the world?

108. Do you believe that universal healthcare is a right?

109. What do you think has been humankind’s best invention?

110. What subject do you think they should add to the school curriculum? 

111. Do you think the world would be a better or a worse place if religion didn’t exist?

112. What basic rights do you think every human being should be entitled to?

113. Do you think the invention of money has benefited or harmed the world?

114. What would be the first law you’d create if you were put in charge of the country tomorrow?

115. What would a world without money be like? 

116. If an alien arrived from another planet, and you could only tell them three things about life on Earth, what would you tell them?

117. Do you think society should introduce a maximum income to decrease inequality? 

118. What one quality does the world need more of?

119. Do you think the world would be a better or worse place if people were always completely honest?

120. Is there ever a justification for going to war?

121. Do you think parallel universes exist? If so, what would your life be like in a parallel universe?

122. What policies would the ideal government have?

123. Could we realistically feed every human on the planet?

“Would You Rather?” Deep Questions

Great for not making the conversation topics too heavy, these “would you rather” questions give you both options to choose from, allowing the conversation to run smoothly and giving you both room to discuss further.

124. Would you rather be an ugly genius or incredibly attractive but unintelligent?

125. Would you rather be a world expert on one subject but lack common sense or be knowledgeable about a diverse range of topics?

126. Would you rather work a regular 35-hour week and retire at 65, or work 75-hour weeks for ten years and then retire?

127. Would you rather be liked or respected?

128. Would you rather be able to watch back your favorite memories like a movie or have the power to erase your worst memories?

129. Would you rather only be able to live in big cities or only be able to live in the rural countryside?

130. Would you rather live for an extra ten years or win one million pounds?

131. If you could time travel just once, would you rather go forwards or backward in time?

132. Would you rather be able to go back and change one moment from your past or foresee one moment from your future?

133. Would you rather know the cause of your death or the date of your death?

134. Would you rather win one million pounds if your enemy would also receive the same amount or not receive the money at all? 

135. Would you rather always be able to tell whenever somebody was lying but never be able to lie or be able to lie but not know when others are lying?

136. Would you rather forget your favorite movie so you could watch it for the first time again or forget your favorite album so you could listen for the first time? 

137. Would you rather earn over $100,000 a year doing a job you hate or earn minimum wage for a job you love?

138. Would you rather be able to fly for one day or be able to read minds for one day?

139. If you were running for office, would you rather amend your policies and win an election or lose the election but keep your integrity?

140. Would you rather have freedom from suffering or freedom to do whatever you want?

Miscellaneous Deep Questions

Generate some thought-provoking conversations with these miscellaneous deep questions about a wide range of topics and viewpoints.

141. Do you believe that some people are born lucky?

142. Is there anything from your past that you’re ashamed of?

143. What’s the best piece of advice you’ve ever received? 

144. If you could pick one memory from your life to watch back, what memory would you choose?

145. If a genie offered you three wishes, what would you wish for?

146. Is every idea based on a previous experience, or is it possible to have a genuinely original thought?

147. Do you think time travel will ever be possible? 

148. If you got a million pounds to donate to a charitable cause, what cause would you choose?

149. What fictional character from movies or television do you most relate to?

150. Have you ever done a kind deed for a stranger, or has a stranger ever done a kind deed for you?

151. What do you wish you had done differently during your teenage years?

152. Do you think you’re most true to yourself when around your friends or your family? 

153. What item could you not imagine living without?

154. Which element best represents you?

155. What was your favorite subject in school? Do you think this subject has influenced your adult life?

156. What do you wish more people knew about you?

157. What’s the most embarrassing thing you’ve ever done?

158. Who or what inspires you in life?

More Questions

Looking for more deep questions to ask someone? Use some of these intriguing questions and deep conversation starters to get lost in each other’s company, maybe even for hours at a time.

159. What three words do you think best describe you and your personality and why?

160. Tell me about one dream you had that you can still vividly remember to this day, and what do you think the dream means?

161. Up to this point in life, what would you say was your biggest regret, and if you could go back in time, what would you do differently?

162. Do you think it is better to prioritize your personal life but be financially vulnerable, or put your career, finances, and setting you and your family up for the future ahead of your own happiness and free time?

163. Do you think you can have multiple best friends, or can there only be one person in your life you can always trust and confide in to a degree no one else can match?

164. Have you ever broken someone’s heart, and if so, do you regret it?

165. What is the craziest thing you have ever done that, to this day, you have hidden from family or close friends?

166. Do you think a past relationship can teach you what you need moving forward, or do you think people are prone to make the same mistakes over and over again?

167. No matter how much you love someone, is there a relationship deal breaker for you that you simply could never get past?

168. What three things do you think are most important in a healthy relationship?

169. Do you believe in love at first sight, or do you think there are many outside factors that need to be addressed for a relationship to work?

170. What is the weirdest thing that has ever happened to you, and did it have a positive or negative impact on you?

171. What is the biggest mistake you have made in life to date, and if you could, would you go back and change it or leave it be?

172. What is the biggest adrenaline rush you have experienced?

173. What do you believe is mankind’s greatest accomplishment to date, and what do you think it will be in the near future?

174. If the world ended tomorrow, what would you do for the rest of today?

175. Do you believe long-distance relationships can work, or are they doomed from the start?

176. Who was your favorite teacher at school, and do you think they had an impact on the person you have become today?

177. When you’re not around, how do you think your friends describe you, and why do you think that?

178. What is your favorite memory of childhood and why?

179. Do you think you should act on a gut feeling or should you try to apply logic to all decisions?

180. What and where would be your perfect vacation?

181. In an age of virtual interactions and social media, do you believe it is harder to make a meaningful connection with anyone?

182. What was the most romantic date you have ever been on, and why?

183. What is the most spontaneous thing you have ever done, and how did it make you feel?

184. If you woke up on a deserted island, do you think you could survive, and what skills do you think you would be able to use?

185. Do you remember your first kiss, and did it mean anything to you?

186. What is your greatest fear in life, and how do you think you would overcome it?

187. Do you believe you have been here before in a past life?

188. Do you believe in soul mates, or do you think there are many people in the world we could potentially be with and build a life together?

189. If you were facing a life or death situation, who is the first person you would want to call, and why?

190. Do you have a guilty pleasure you share with barely anyone, and would you be willing to talk about it now?

191. What did you learn from your last relationship?

192. What did a past relationship teach you about yourself and what you need to be happy, if anything?

193. Do you think you should ask deeply personal questions on a first date and try to know straight away if you would be able to love that person, or is it better to keep things light-hearted and casual so as not to come across too intense?

194. Do you think two people can not be in a romantic relationship but still love and care for each other?

195. Does anyone important in your life have bad habits you worry will one day put them in serious harm?

196. Do you have a memorable experience in your life you wish never happened, and why?

197. What have your previous relationships taught you about yourself?

198. Do you believe you can find true love on a dating game show?

199. In these difficult times, do you think it is better to try and save money and do fewer things, or continue to go out and experience things with friends and loved ones but know life will continue to be financially unstable for you?

200. Do you think long-distance friendships can give you the required trust and deep connection you need to consider someone your best friend?

201. To date, what would you say is the best phase of your life, and why?

There comes a time when you’ll want to get to know someone on a deeper level, be it a budding friendship, reconnecting with someone, or a romantic partner.

These deep questions will help move the conversation beyond the filler and the light-hearted and allow you to really open up and get to know someone in a meaningful way.

Oh, and here’s some other question-themed articles you may want to read:

Keep these 200+ amazing deep questions for safekeeping, by saving this article to one of your Pinterest boards.

100+ Deep Questions To Really Get To Know Someone (questions 1-14 listed above).