225 Deep Questions To Ask Your Boyfriend

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225 Deep Questions To Ask Your Boyfriend

Sometimes it can take years to get to know your boyfriend fully. While uncovering new things about your partner is part of the joys of falling in love, it helps to push this process forward by having open and honest conversations that bring you two closer together.

Who wants to be several years into a relationship before you discover your partner doesn’t have the same goals as you, or doesn’t see eye to eye with you on important issues? 

These questions will ignite deep conversations that will make you two feel more connected. You can make plans together and be comforted in the knowledge that you’re headed on the right track. 

Here are 225 questions to ask your boyfriend and get to know him on much deeper level.

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1. What does your perfect day look like?

2. What is your biggest fear?

3. Who is your hero?

4. What qualities do you admire about me? 

5. What qualities do you admire about yourself? 

6. What is the biggest doubt you have?

7. Do you consider yourself an introvert or an extrovert?

8. What are you most thankful for?

9. Who do you miss most in your life?

10. Which parent are you closer to and why?

11. If you could live in someone else's body for a day, who would it be and why?

12. What would you tell your younger self? 

13. What is on your bucket list this year?

14. Were you attracted to me right away?

15. What is the most useful skill you have?

16. What is your biggest success?

17. How do you feel about sharing your password with your partner?

18. When were you happiest in your life?

19. What qualities do you admire about your parents?

20. What qualities do you least admire about your parents?

21. If you could only listen to one song for the rest of your life, what would it be?

22. When were you the unhappiest in your life?

23. What do you do to get out of negative headspaces? 

24. Do I have traits that are important to you in a relationship?

25. If a genie granted you 3 wishes right now, what would you wish for?

26. Have you ever been in love?

27. Does your job make you happy?

28. If you could change one thing about me, what would it be? 

29. What is the one thing you would like to change about yourself?

30. Have you ever cheated on someone?

31. Would you ever take back someone who cheated?

32. What is a relationship deal-breaker for you?

33. What about a person first attracts you? 

34. When do you think a person is ready for marriage?

35. Do you want children? 

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36. How many children do you want? 

37. What is the most embarrassing thing that’s ever happened do you? 

38. If you could be a woman for the day, what would you do? 

39. What is something you’re afraid to tell me? 

40. What words hurt you the most to hear? 

41. If you could have a superpower, what would it be? 

42. What values do you want your children to possess?

43. Are you pursuing your dream job?

44. Have you ever lost someone close to you?

45. Have you ever been heartbroken?

46. If you're in a bad mood, do you prefer to be left alone or have someone to cheer you up?

47. What is the most daring thing you’ve ever done? 

48. What is the one thing that people always misunderstand about you?

49. What places do you want to travel to the most?

50. What makes a long-lasting relationship?

51. Have you ever broken someone’s heart?

52. Would you move state/country for love?

53. What did you want to be when you were younger?

54. What word or phrase do you live by?

55. What are your top 5 favorite movies?

56. What would you do if your parents didn’t like your partner?

57. Do you believe in fate? 

58. What is your favorite book and why?

59. Are you religious or spiritual?

60. When have you felt your biggest adrenaline rush?

61. Why did your last relationship end?

62. Have you ever been in a physical fight?

63. What do you wish was better in our relationship?

64. If you could go back in time, where would you go?

65. Do you consider yourself ambitious?

66. Are you confrontational?

67. What do you consider a wasted life?

68. Do you usually stay friends with your exes?

69. What has shaped your political beliefs? 

70. What kind of parent do you think you will be?

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71. When did you decide you wanted us to be official?

72. Do you judge a book by its cover?

73. What is your biggest regret in life?

74. What was your first impression of me? 

75. If you were stranded on a desert island, what 3 items would you want with you?

76. Who is that one person you can talk to about just anything?

77. Do you think I would make a good parent? 

78. What movie influenced you the most?

79. What is an ideal weekend for you?

80. Are you afraid of failure?

81. Who do you look up to? 

82. Were you nervous before our first kiss?

83. Would you take on your significant other’s religion if they had one?

84. Do you believe in second chances?

85. When is the last time you said “I love you” to someone?

86. What has been your biggest mistake so far in life, and what did you learn from it?

87. Where is your favorite place in the entire world to go? 

88. You have to put your life on the line for one person, who would it be?

89. What did your past relationship teach you?

90. If you only had one day to live, what would you do? 

91. Why do you like spending time with me?

92. What was your biggest passion as a child?

93. Would you rather have your dream car or your dream house?

94. Would you take a bullet for someone?

95. What is your worst habit?

96. Do you ever feel nervous around me now? 

97. What do you do when no one is watching?

98. Are you afraid of the dark?

99. Where is the perfect place to go on a date?

100. When was the last time you cried?

101. What is the nicest thing I’ve ever done for you? 

102. What is the best birthday gift you’ve ever received?

103. What was the worst book you ever had to read?

104. If you couldn’t fail, what is one thing you’d do?

105. Are there any movies that bring a tear to your eye?

106. Do you believe in love at first sight? 

107. What do you wish your phone could do right now?

108. What is your favorite sport and why? 

109. Do you think I’m the one? 

110. What would be your death-row meal?

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111. Do you prefer to travel alone or with friends?

112. How many countries have you visited?

113. If you won $1 million tomorrow, what would you spend it on?

114. What do you think the next big technological discovery will be?

115. What do you own that has the most sentimental value to you?

116. What is your own definition of a waste of money?

117. If your relationship was taking a downturn, what would you do to save it?

118. Have you ever gotten back with an ex?

119. What are your biggest goals in life, and what have you done to achieve them?

120. Would you rather no one came to your funeral or no one came to your wedding? 

121. What is the biggest lie you’ve ever told?

122. Do you believe in karma? 

123. What is the best part about dating me?

124. What is the worst part about dating me?

125. What lesson have you learned the hard way?

126. What is the one thing that has kept you going during tough times?

127. What would you not do for a million dollars?

128. Would you rather have a job or be your own boss?

129. Who is that one person you’re comfortable discussing anything with?

130. Who are the kind of people you can’t stand?

131. Do you want to follow traditional gender roles in your household?

132. Who is the most important person in your life right now outside your family?

133. What is your most priced asset?

134. What is the biggest lesson you’ve learned from our relationship? 

135. What is unforgivable to you?

136. When did you know you loved me? 

137. What event would you rather die than have to go through?

138. Looking back, what is the one thing you wish you never did?

139. What are you usually thinking about when we’re kissing?

140. What is your favorite body part of mine?

141. What is your favorite place for making love?

142. Do you like to cuddle?

143. Would you rather hug me for 6 seconds or kiss me for 2 seconds?

144. Would you rather lie to keep a relationship going or tell the person the truth and risk breaking up?

145. What are some of your rules that bend for no one?

146. Would you rather be hated for standing by the truth or loved for telling lies?

147. What do you want people to say when you die?

148. What is the one thing or person you can lay down your life for?

149. If your home was burning down, what 3 material items would you save?

150. What is the biggest risk you’ve ever taken that paid off? 

151. What job do you think you could lie your way into with no experience and no one would notice?

152. If you could live forever, would you want to?

153. Have you ever thought about ending our relationship?

154. What do you remember most about meeting me? 

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155. What is the most interesting fact you know?

156. What do you dream about? 

157. What is a question you’ve never been asked that you would like to hear? 

158. Do other people’s opinions matter to you? 

159. Which historical figure would you have dinner with if you could? 

160. What are 3 events that have had the biggest impact on who you are today? 

161. What change would you like to see in the world? 

162. What do you consider a waste of a life?

163. How have I shaped your life? 

164. If you could become an expert in any field, what would it be? 

165. What is society doing now that will be ridiculed in 20 years? 

166. Who, in history, is overrated? 

167. What are you tired of hearing about?

168. What causes you stress

169. Do you believe in soulmates? 

170. What are you doing to improve the world? 

171. If you had to describe our relationship in one word, what would it be? 

172. What is our biggest similarity? 

173. If you had the option to hit restart and begin life all over again, would you?

174. What is one thing that totally relaxes you when you’re stressed?

175. What is a hobby you’ve always wanted to try but never have?

176. What scares you the most about the future?

177. Where do you want to settle down?

178. What is something you accomplished that you never thought you would?

179. What is one thing you could never live without?

180. Who is one person you could never live without?

181. What is your favorite vacation place?

182. Would you rather go out or stay in on a Saturday night?

183. What is your favorite quote, line of poetry, or sentence?

184. What is your favorite family memory?

185. Do I inspire you?

186. What is one thing that helps you decide you can trust someone?

187. How would you explain what love is?

188. What is your best memory with someone you longer speak to?

189. What is the craziest thing you’ve done for love?

190. What is your biggest turn-off?

191. What is your biggest turn-on?

192. How would you describe me in 3 words? 

193. How would you describe yourself in 3 words? 

194. What is the scariest thing that ever happened to you as a kid?

195. Who in your family, immediate or extended, are you the most similar to?

RELATED: 100 Deep Relationship Questions To Ask Your Fiancé Before Getting Married

196. Who would compose the soundtrack to your life? 

197. Do you think couples should keep secrets from each other? 

198. Where do you see yourself in 5 years?

199. What would be your dream job?

200. If you were writing a book about your life, what would the title be?

201. What is your favorite word?

202. Have you ever said “I love you” without meaning it? 

203. Do you think we’ll stay together forever? 

204. What keeps you up at night?

205. What is your go-to phrase?

206. What is one toy or item you’ve kept since childhood?

207. What is one thing you’ve learned from me? 

208. Who has had the biggest impact on your life?

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

210. What is the best advice you’ve ever received?

211. What is the worst purchase you’ve ever made? 

212. Who is your favorite author?

213. Who of your family and friends knows you best? 

214. Would you stay with me even if your friends hated me?

215. What do you believe happens to us when we die?

216. What was the biggest mistake made in history?

217. What is the best bad decision you’ve ever made?

218. What is your favorite memory with me? 

219. What is your definition of a “real man”?

220. What game do you always lose? 

221. What is the biggest thing in your way?

222. Who is your best friend? 

223. What is the longest amount of time you’ve spent being angry at me? 

224. What is your guilty pleasure?

225. What makes you blissfully, completely, smile-from-ear-to-ear happy?

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Alice Kelly is a writer with a passion for lifestyle, entertainment, and trending topics.