Inspiring meaningful connections & fun, happy lives...


Join Our Newsletter


201 Deep Questions to Ask that Uncover Hidden Thoughts

In our quest to learn more about each other, our list of deep questions to ask is such a fun way to uncover their secret thoughts, feelings and desires.

What are some deep questions to ask?



We have questions to help you get started. Below you will find questions that you can use or change to fit your relationship better. 


Most questions to ask could be mixed and matched, so read through them all to find ones on the topics that you would like to learn more about.

What is a good deep question?


A good deep question is anything that allows you to dive into subjects that would normally take a long time to learn about someone.


Instead of finding that perfect moment to discuss serious topics, asking deep questions turns it into a game of sorts.


You can learn about their future plans, the insight that they have into their own personality and how their past has shaped who they are today. These are all topics that take a while to learn about a person and asking questions allows you to speed up the process. 


Finding out what is truly important to a person is so important to knowing whether could be a good match or if your relationship needs to focus on certain areas.


deep questions to ask a guy image


Deep questions to ask a guy 


1.What is the first thing that you would do if you found out you had a week to live?

2. Have you done most of the things you have always wanted to do by this point in your life?

3. What social problems are you most concerned about?

4. Have you ever been to a protest?

5. What are your political views?

6. Are you hopeful about the future?

7. What is your love language

8. How important is it to you to keep your word?

9. Are you someone that likes to be physical in public? Around your family?

10. What was your last girlfriends best quality?

11. What would you like your life to look like in 10 years?

12. Do you see marriage and kids in your future?

13. Who has the best marriage that you have seen up close?

14. Have you ever cheated on someone while you were dating or in a relationship with someone?

15. Are you a light or a heavy sleeper? 

16. What changes have you made in your life recently?

17. Do you generally trust women?

18. Are you friends with any of your ex’s?

19. What is something that you cut corners doing just to get it over with?

20. When was the last time that you really laughed?

21. What makes a life meaningful?

22. What fear do you have about your life or future?


More deep questions to ask a guy


23. Do you believe in science or are you more of a conspiracy person?

24. How important is it to you to have a family?

25. What goals do you have for your career?

26. Would you relocate for your career?

27. What has changed at your place of work since the “Me too” movement?

28. Have you ever been cheated on?How did you feel about that and what did you learn?

29. What is your favorite way to get exercise?

30. What do you do when you feel uncomfortable?

31. If you had the power to really influence people, what would you do?

32. What is a book that has made a real impression on you?

33. How much money would it take for you to feel wealthy?

34. Have you ever had to take care of something or someone? Pet, sibling or plants?

35. What are the most important qualities that you want in a girlfriend/wife?

36. How loyal of a person are you?

37. Do you believe in fate or that things just happen randomly?

38. What would you like to change about your personality?

39. Do you enjoy learning?

40. What is more your style; a modern home in the Hollywood Hills, a beautiful mountain retreat or a bungalow at the beach?

41. What would it take for you to feel successful?


Deep questions to ask your boyfriend 


42. Who do you know in your life that you feel sorry for how their life turned out?

43. Would you consider yourself a very honest person?

44. What are some good reasons to lie to someone?

45. Would you rather tell a white lie or be honest and maybe hurt someones feelings?

46. How many hours can you play video games?

47. Who in your family do you look up to the most?

48. If you could redo a time in your life,  what time comes to mind?

49. How often do you have a drink?

50. What was your experience with your state’s quarantine?

51. Is there anyone close to you that has an addiction problem?

52. How much of your pay do you set aside to save?

53. Where do you get your news from?

54. How upset do you get when your sports team loses?

55. What do you think of the Black Lives Matter protests?

56. Do you know anyone with a chronic illness?

57. What is the best part of being single?

58. Do you like to cuddle?

59. What do you wish women knew about men?

60. Do you believe in second chances or one and done?

61. What are your top deal breakers in relationships?

62. Do you believe in love at first sight or lust at first sight?


More deep questions to ask your boyfriend


63. What would be your choice for your funeral? Traditional, cremation with a special location or more of a celebration?

64. Will your job likely ever be replaced by robots?

65. Do you have faith in humankind?

66. Would you rather argue or not discuss something when you have disagreements with someone?

67. What failure taught you the biggest lesson?

68. What is your reaction when you see someone crying?

69. How long could you be without your phone before you go nuts?

70. What moves you? Music, art, sports?

71. What is something that you did that a previous partner complained about?

72. What experiences and people in your life are you grateful for?

73. When you get upset, would you rather be left alone or do you like to talk it out?

74. Is there something that you love spending time on?

75. What hobby or skill would you like to learn more about?

76. Do you have an inspirational person that you turn to for great quotes?

77. What goal do you have for the upcoming year?

78. When you get food cravings, what are they likely to be?

79. If I asked you for a romantic meal, would you cook one for me?

80. What was the last thing that you did that was really out of your comfort zone?

81. Is there something that you can think of that you would need some encouragement to achieve?

82. Did you grow up with healthy role models?

83. We all have some dysfunction in our extended families, who would you put into that category?


deep questions to ask your girlfriend image


Deep questions to ask your girlfriend 


84. All of us have a loose timeline of ages that we would like to accomplish things, are you happy with what you have achieved so far?

85. Have you ever gone to a protest? 

86. What social problems do you feel the strongest about?

87. How would you describe your political views?

88. Are you hopeful about your future?

89. Are you a lot like your mother?

90. What do you think it takes to have a good marriage?

91. Would you describe yourself as adventurous?

92. What was the most adventurous thing that you have ever done?

93. Have you ever cheated on someone in a relationship?

94. What age would you like to be married by?

95. Do you see children in your future?

96. What kind of mom do you think that you would be? Do you think you would be very strict or pretty lenient?

97. What was your last boyfriends best quality?

98. Are you able to relax or do you always want to be doing something?

99. Have you ever asked for a promotion?

100. How did you handle your area’s quarantine?

101. What changes have you made in your life recently?

102. What do you wish men knew about women?

103. Do you generally trust your judgement with men?

104. Have you ever been harassed in school or at work?

105. Are you religious or more spiritual?

106. What are your favorite healthy habits? Workouts?

107. Do you cry at movies or touching commercials?

108. Would you mind if your guy was good friends with his ex?

109. What would success look like to you?

110. What are the most important qualities in a partner?


21 deep questions to ask your boyfriend & girlfriend infographic


More Questions to ask your girlfriend


111. What religious traditions would you want for your family?

112. List your top 5 deal breakers in a relationship.

113. Do you believe in love at first sight?

114. Has anyone ever cheated on you? What happened?

115. Do you believe that most people are inherently good?

116. How vain do you think that you are?

117. Did you argue often in your previous relationships? Why do you think you did or did not?

118. Do you believe that you can achieve anything that you set your mind to?

119. What do you enjoy that is creative?

120. What movie would you consider your absolute favorite? Why?

121. How long could you survive without your phone?

122. Name something about yourself that you wish more people knew.

123. Have you lost anyone in your life that you were really close to?

124. What is one thing that you would like to change about your personality?

125. Do you like to look forward to the future or are you more nostalgic for the past?

126. Do you hold a grudge or get over things fairly quickly?

127. What are you motivated to achieve in your life?

128. What is something that really annoys you?

129. Do you have a love of life?

130. When you get knocked down and discouraged, how do you react?

131. What is your greatest strength?


21 deep questions to ask that uncover hidden thoughts infographic


Deep questions to ask your crush 


132. What do you love to do on your birthday?

133. Would you rather spend time with your boyfriend/girlfriend or receive a a gift from them?

134. How long was your longest relationship?

135. What social media do you spend the most time on?

136. What personality traits would your friends use to describe  you?

137. Do you like to spend a lot of time alone?

138. Are you a jealous person when you are in a relationship?

139. What is your families nationality? Do you practice any family traditions of a specific nationality?

140. What are your favorite traditions?

141. Do you like being part of a couple?

142. What do you want your eulogy to say?

143. Would you rather go on a sunrise or dusk walk on the beach? 

144. Have you ever camped out under the stars? What was your favorite camping food?

145. When you think of embarrassing moments…What comes to your mind?

146. What childhood memory do you have that makes you nostalgic?

147. Do you believe that people can change if you really want them to?

148. Have you ever survived a dangerous situation?

149. Have you ever worked really hard to reach a goal? How did you feel?

150. What emotion are you more likely to feel, guilt or regret?

151. Do you ask advice from friends or family?

152. How often do you talk to your mom or dad?

153. Do you stand up for yourself or are you more shy?

154. What happened on a day that you will never forget?

155. What destination do you dream about visiting?


Deep questions to ask friends


156. What reasons would you consider lying to your friends?

157. Whose life would you like to emulate?

158. What female celebrity would you like to go on a weekend getaway with?

159. Name a male celebrity that you would like to date? (imagine that you are single)

160. What famous couple do you think made a great pair?

161. Have you ever taken anything that did not belong to you?

162. What have you accomplished that you are proud of?

163. What is/was your favorite thing about being single?

164. Have you ever visited a psychic? Did anything they said come true?

165. What would you do on a “perfect day?”

166. Do you check your astrology readings? What zodiac sign are you?

167. Who do you tell all your secrets to?

168. Are you someone that can just start dancing by yourself when at a party?

169. Do you think being famous would be fun or would it be something to survive?

170. What is something that really pisses you off?

171. What do you think about the most?


Funny deep questions 


172. Name someone that you had a crush on, that you later found out was a horrible person.

173. What was the most stupid thing that you have done in a relationship?

174. How often have you cyber stalked your ex?

175. What is a quirk that everyone knows about you?

176. Who was the craziest person that you were friends with?

177. What was the most amount of money that you have lost gambling that you never told anyone?

178. Did you ever get into a physical fight with someone? How long ago?

179. What irrational fear do you have and to what lengths will you go to avoid?

180. Do you like knowing that you have money set aside for something in the future?

181. Would anyone describe you as being easy going?

182. If someone told you they saw a ghost, would you believe them?

183. What do you think is a more powerful motivator, the love of a person or the love of money?

184. Do you ever have nightmares? What was the last one that you remember?

185. How easy is it to talk you into something that you are hesitant about?

186. If you have brothers or sisters, are you the good sibling?

187. Do you choose the easy or the hard way, more often?


deep questions to ask a guy image


Deep yes or no questions 


188. Do you consider yourself a happy person?

189. Could you ever vote the opposite political party?

190. Would you give up creature comforts to volunteer in another country?

191. Do you make decisions based on a companies social focus?

192. Can you be a selfish person?

193. Do you complain when you have chores to do?

194. Would you like if someone threw you a surprise party?

195. Do you every worry that you have some type of addiction?

196. Do you understand the stock market?

197. Would you ever go rock climbing?

198. Do you focus on the negative?

199. Can you be rebellious?

200. Lets say that you really hoped for a special gift, but instead you received something that wasn’t at all what you wanted. Do you tell them you are disappointed?

201. Would you be happy if you never had to work again?


Conclusion deep questions to ask


Relationships can always be challenging, but one way to stay or get on the same page is to communicate often. 


The truth is that no one likes to be interrogated and some topics are more difficult to bring up.


 Taking time to ask questions on your date night while taking a walk, helps to jump start conversations that are fun and informative.

 We have 1000’s of questions to ask for many different relationship situations.


Have fun and choose the questions and topics that you are the most interested in learning more about.

The key is to listen to the answers to learn the most about each other and your views on all these important subjects.

Always ask “why do you think that?”


250 Questions to get to know someone

175 Fun Questions to Ask to Get to Know Someone

130+ Ice breaker Questions & Texts to have Amazing Conversations

125+ “How Well Do You Know Me?” Questions for Couples

36 Questions to Fall in Love

Questions to Ask your Crush that are Flirty, Funny & Cute

21 Questions to Ask a Guy to Start a Conversation

110 Good Questions to Ask to Increase Intimacy

95 random questions to ask for fun conversations

Funny Would you Rather Questions to ask Couples and Friends

What are the Best Date Night Questions?

13 First Date Conversation Starters + What Not to Say on a First Date

73 First Date Questions That lead to Insightful Conversations

80 Conversation Starters for Texting that Spark Connections

Share this article