250+ Deep Questions to Ask About Life, Love & More

-Deep Questions to Ask­-

You ever posed serious questions to your boyfriend? Well, even before you arrived on the scene, your lover had a full life filled with embarrassing experiences, high successes, and failed relationships. Asking the right questions could sustain a relationship.

Deep Questions to Ask a Friend

1. What’s something that you are glad you will never need to do again in your life?

2. What would you do with a billion bucks if you were given it all at once?

3. What should people in a healthy relationship get out of it?

4. Do you believe that everything happens for a reason, or do we just come up with explanations after the fact?

5. Is there anything that you absolutely refuse to forgive?

6. What would you do first if you wake tomorrow without fear?

7. What has been the biggest benefit in disguise in your life?

8. Which year of your life would you like to get a do-over, and why?

9. What is one thing you will never put up with?

10. What three words would you write to your younger self if you could only write one?

11. What is it about you that makes you feel like you’re alive?

12. What’s something that you always procrastinate on?

13. What does your ideal day necessarily involve?

14. Do you follow your mind or hear while making any important decisions in your life?

15. What do you think will never end well?

Great Questions You Need To Ask

16. If you would be able to change anything related to the way you were raised, then what would you like to change?

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17. If you get a chance to live in someone’s body for a day then who it would be and why?

18. What are some of your excellent qualities that you admire a lot?

19. What is something in your life that you’re most grateful for? Is it family, job or career?

20. What are your long term wishes that you want to come true?

21. What are the special qualities of your parents that you admire most and talk about often?

22. Is there anything that you want to change about yourself? Or, are you fine with who you are?

Deep Questions to Ask a Guy

23. According to you, what is the right age to get married or when a person is ready for marriage?

24. What are some of the values that you want your children to possess?

25. What is one thing that people consistently misinterpret about you?

26. What is something that makes a relationship long lasting? Is it understanding, love, wealth or something else?

27. Are ambition and goals important in a relationship? If so, then why and what can you do to achieve them?

28. What is your biggest mistake in your life so far and what did you learn from that?

29. If your relationship or marriage life was taking a downturn then what would you do to save it?

30. What is something that helps you stay motivated during tough times?

31. Name one the person who is comfortable discussing anything about your personal and professional life.

32. Who is the one person or one thing you can lay down your entire life?

33. What is one thing that you want to achieve before you die?

Deep Questions to Ask Someone

34. If you get a chance to live forever, would you choose to live?

35. What is something that you are doing to improve world scenarios and why?

36. What is something you think to be real that no one else believes to be true?

37. What is your greatest life fear so far?

38. How do you calm down yourself in case of anger or panic? Any technique or tool?

39. What’s your favorite music and how does it make you feel?

40. What is the most emotional scene you have watched in a movie that made you cry?

41. Do you like to spend your time alone? What do you like to do when you are alone?

42. When do you have the feeling of being most alive? Can you tell me something about this?

43. What do you opt to ignore because it’s too difficult to bear?

44. What are some of the people that you enjoyed most when being around?

45. Do you feel that you are living your life to the fullest? If not, then why?

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Deep Questions to Ask People

46. Is religion bad or good for work? What’s the impact of religion on people?

47. What is the biggest secret you have kept from someone?

48. What is the most important issue in politics or society that should be solved?

49. What has been the biggest change in your life so far that you have been most proud of?

50. What do you like to do for the people around you who you love the most in life?

51. When you hear the word home then what’s the first thing that comes to your mind?

52. If you want to go anywhere in the world right now then where would you like to be?

53. If you get a chance to travel back in time for one day then which year would you like to visit and why?

54. Do you think that there is something more in reality than what we see with our eyes?

55. Do you think that the universe is ever really meaningless? Or does it really have a purpose?

56. If you get a chance to erase the pain from your life then would you do that?

57. If you can give the date of year death then what would you want to know?

58. If you could ask me one question and I had to answer honestly then what would you ask?

59. Would you like to live a short and exciting life or a long and boring but comfortable life?

Deep Questions to Ask your Best Friend

60. When was the last time you slept outdoors?

61. What is something that you are proud of about yourself?

62. What song do you often sing in the shower?

63. What do you feel is the right age for people to get married?

64. What would be your super villain name and your powers?

65. What three non-electric or non-automatic items would you take on a deserted island?

66. If “hello” were to be replaced by another word as a greeting, what word would that be?

67. What is the weirdest thing that your family does together?

68. What was the most embarrassing thing that you’ve done for a friend?

69. What task would you really fail at doing?

70. What is your definition of a “perfect life”?

71. What would be the title of the movie showing your life from birth up to present?

72. What fashion piece would you invent for women?

73. What is the single most important thing people should do for the planet?

74. How do you define evil, and do you believe that a person can be evil?

75. Do you listen to other people’s advice, or do you prefer figuring things out yourself?

76. What is your favorite motivational quote?

Questions About Purpose

78. Imagine that you are tasked to re-design society – what changes would you make?

79. What’s the perfect day for you?

80. Would  you wait for the sun to rise or for it to set, and why?

81. If you were born in another era, when would that period in history be and why?

82. Have you made someone cry?

83. What is the most astonishing act that a person can do for you?

Deep Questions to Ask Your Partner

84. What ability do you possess that you’d think others would find amazing?

85. Have you ever stayed up all night to wait for sunrise?

86. When was the last time you slept under the stars?

87. Would you rather be a world-famous pro-MMA athlete or the president of a country?

88. Can you remember the last time you cried, and what was the reason?

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89. Who do you feel is your closest confidant among your family members?

90. If you were given a million dollars today, how would you spend it within three days?

91. What two items would you need to survive an apocalyptic zombie invasion?

92. When you were growing up, which superhero was your favorite, and why?

93. What is your funniest memory of high school?

94. How would you spend your remaining time if you found out you only had 10 days left to live?

95. What’s one item you’ve recently crossed off your bucket list?

96. Do you have a favorite place in the world, and where is it?

97. Are you a cat or a dog person, and why?

Best Questions for You

98. Are you more afraid of failure or success, and why?

99. What was your most memorable birthday?

100. At what age did you have your first pet, and what was it?

101. What things or situations make you feel unsure about yourself?

102. What do you feel is your greatest accomplishment to date?

103. What would you do for the people you love?

104. At this point in your life, what is it that you wish your family knew about you?

105. When was the last time you said “I love you” to someone?

106. If you have to lay your life on the line for someone, who would that person be?

Deep Questions to Ask Mentors

107. What gives your life meaning?

108. What would your three wishes be if someone could make them come true?

109. Are you willing to lay down your life for someone, and who is it?

110. What top five lessons have you learned the hard way?

111. Do you believe in magic or in science?

112. What would the world be like if you hadn’t been born?

113. What is your definition of fame?

114. Do you wish to be famous?

115. What would you want to be famous for?

116. What is the greatest invention of this age?

117. Would you be willing to go the extra mile for something or someone?

118. Which one wins: reality or imagination?

Deep Questions to Ask About Life

119. When was the last time you said “I love you” to your parents?

120. Who do you look up to in life?

121. Do you give advice to others, and why?

122. Which is the better option: being a heartbreaker or being heartbroken?

123. If you could swap lives with someone for a day, who would you choose and why?

124. Which emotion best represents you, and why?

125. What do you think will bring about humanity’s extinction?

126. Do you feel happy when you use social media?

127. Will you encourage the younger generation to use social media?

128. If you had a billion dollars, how would you use the money to benefit the less privileged?

129. Which one is a better situation: broke or lonely?

130. When you die, would you prefer to be alone or surrounded by people you know?

Deep Questions about Purpose

132. What’s the highest point you’ve experienced in your life this year?

133. who’s hiding behind the mask you present to the world?

134. Is your life going in the direction you want?

135. If your life was a movie, what would the title be and why?

136. Have you experienced any miracle in your life?

137. Does art have any significance in society?

138. On a scale of 1 to 10, how fulfilled are you about life?

139. When was the last time you were moved to tears by a movie?

140. How do you define “a life well lived?”

141. What regrets would you have if you were to die today?

142. Can humans avoid being in love?

143. Is there such a thing as absolute freedom?

144. If you were given free rein to design the ideal metropolis, what would your city be like?

145. Is there such a thing as lasting peace?

Deep Question you Ask Yourself

146. Do you approve of stealing from the rich to give to the poor?

147. Do you believe that each one of us has a special mission in life?

148. Do I like who I am right now?

149. When was the last time I laughed so hard?

150. What would I truly regret not doing if I died tonight?

151. What advice has someone in my family given, and that I have taken just in time?

152. What were the top three lessons I learned the hard way?

153. What would I do if my biggest fear came true?

154. What would I do with my remaining days if I had only a year left to live?

Questions You Must Ask Yourself

155. Am I a servant of money, or does money serve me?

156. Why am I afraid of being true to myself when others are around?

157. What are the three things that I am most grateful for?

158. Have I done something recently that I could be proud of?

159. When was the last time I extended kindness to somebody?

160. What question do I want to know the answer to if it will help humanity?

Deep Questions for Self Growth

161. What aspect of my personality still needs improvement?

162. Must I take other people’s advice?

163. What annoys me the most?

164. Do others find me likeable? (These social habits can make you more likeable.)

165. When was the last time I fell head over heels with life?

166. Am I enriching other people’s lives with what I do?

167. How meaningful is my life?

168. What makes life meaningful?

169. Would I lay down my life for somebody?

170. How much money would I be willing to give to those in need if I won the lottery?

171. The day that I would like to live over and over is _________________.

172. Am I worthy of being loved?

173. What talents or skills do I have that I can do better than anyone else?

174. What are the things that put me off?

175. My perception of fame is ________________________.

Deep Existential Question

176. What is a peaceful life?

177. The most important aspect of a potential partner’s personality is ______________.

178. My greatest wish is _________________.

179. What am I most afraid of about life?

180. If I had not been born, what would be different about the world?

181. The three important lessons that I should have learned 10 years ago were: _______, __________, and ________?

182. If I could tell my 18-year-old self one thing, it would be _____.

183. If my life was made into a movie, the title would.

184. Would I enjoy watching a movie made of my life?

185. Is my definition of success the same as everyone else’s?

186. Do I have a personal mission?

187. How would I describe the perfect day?

188. What am I willing to go the extra mile for?

189. What are my top five negative habits that I must change to something better?

Deep Role Models Questions

190. Who do I look up to?

191. What outstanding qualities should my best friend have?

192. When was the last time I told someone I love him/her?

193. Am I satisfied with the quality of my romantic relationship?

194. When have I compromised my personal beliefs because I was afraid to be left out?

195. What skill do I possess that I can do better than others?

196. How often have I said yes when I wanted to say no?

197. What important lesson have I learned this week?

198. What three words would my friends use to describe me to strangers?

199. Have I intentionally broken someone’s heart?

200. Do I really listen when people talk to me?

201. What surprised me about myself this week?

Deep Thought Provoking Questions

202. How many hours have I been spending on the Internet?

203. Do I engage in negative self-talk?

204. Am I living a simple or complicated life?

205. How can I simplify my life?

206. Are there things that I should have done when I was younger that I can no longer do now?

207. What would I change if I were the most influential person in the world?

208. When was the last time I kept in touch with my family, and for how long was it?

209. When was the last time I tried something new?

210. What stresses me out the most?

211. How can I make my life easier?

212. When was the last time I gave something without expecting anything in return?

213. What is the most challenging experience I’ve overcome in the last five years?

Deep Self-reflection Questions

214. Am I spending enough time doing the most important thing in my life?

215. What message can I share with the rest of the world?

216. How easily do I get discouraged?

217. What was it that I never told someone and still regret not telling them?

218. How assertive am I?

219. How old or young do I feel inside?

220. Do I resent others whenever I give in to their wishes?

221. What am I holding on to that I need to let go of?

222. If I were given an envelope containing the date of my death, would I open it?

223. Who among the people I know bring out the best in me?

224. Do I often make excuses?

225. What would I ask for if one of my wishes would come true?

226. Have I matured because of challenges or because of the enjoyable moments in my life?

Deep Self-awareness Question

227. Would I ever choose the easy way in life?

228. What’s standing between me and my greatest dream?

229. Where will I be five in years?

230. When was the last time I was furious?

231. What can I do to make a difference in people’s lives?

232. If failures are the best teachers, why is it so bad to fail?

233. Is it wrong to steal in order to feed a starving child?

234. What should I spend more time doing?

235. Am I missing someone today?

236. What mistake will I never make again?

237. How do I make the most out of life?

238. When was the last time I gave up on something that meant so much to me?

Deep Questions to Ask Yourself

239. Who are the people I truly love, and what am I doing for them?

240. Do I ask questions, or am I content with what I know in life right now?

241. Would I be happy if I never had to work again?

242. Where do I find inspiration?

243. What can’t I live without?

244. Can I live without money, or without love?

245. When was the last time I lost track of time while doing something?

246. What would you do if your parents did not approve of your partner?

247. Do you believe that people of the opposite sex can be the best of friends?

248. Have you ever lost someone who’s very close to you?

249. Who is the person with whom you can talk about anything?

250. Do you believe in burning bridges when it comes to exes?

251. Do you prefer someone cheering you up, or being left alone when you’re in a foul mood?

252. How judgmental are you?

253. What’s the lowest point in your life this year?

Frequently Asked Questions

If you Could ask your Future Self a Question, What Would you Ask?

Are there any people you need to warn or tell me about? Do you have any regrets? If yes, what should I do to eliminate my chance of sharing those regrets in the future?

What are Some Interesting Questions to Ask your Partner?

‣ When was the first time you said “I love you” to someone in your life other than family?

‣ When and where did you go on your first date ever?

‣ Do you remember our first date?

‣ Were you nervous during our first kiss?

‣ When did you know you loved me?

‣What is your ideal night?

What’s the Most Interesting Question to Ask Other People?

‣ Who is your hero?

‣ If you could live anywhere, where would it be?

‣ What is your biggest fear?

‣ What is your favorite family vacation?

‣ What would you change about yourself if you could?

‣ What really makes you angry?

Why are People so Scared of Deep Questions about Life?

People fear what others will think of them when they hear the answer.

What are Deep Questions that I can Ask my Boyfriend?

‣ Do you want to have children?

‣ How long was your longest relationship?

‣ Have you ever been engaged or married?

‣ Have you ever lived with a partner?

‣ How important is religion or spirituality to you?

‣ How do you feel about gay rights?

‣ Do you think money can buy happiness?

As an Older Person, What Questions do you Love to be Asked?

‣ Who am I? Is it who I wanted to become?

‣ Am I happy?

 ‣ Do I love myself? 

‣ Do I love everyone else around me?

‣ Do I respect them?

‣ What’s the goal in my life?

It is always important to understand the sort of questions you will love to ask and how to ask them in other to keep a great conversation.