All relationships that last a lifetime have one thing in common – an understanding for each other and the respect that comes with it.

There is no better way to know and understand how your boyfriend or girlfriend feels about you and the direction your relationship is taking than by asking subtle questions every now and then.

One BIG mistake we commit most often is assuming that everything is right. Just because you are happy and no issues are popping up doesn’t mean everything is okay.

There is a need for you to get to know each other in a more meaningful way especially when everything seems to be going in the right direction.

In this article, I have prepared a list of deep questions to asked your boyfriend over text or in-person the next time you meet.

Unlike fun questions, deep questions to ask your boyfriend help you understand your position in the relationship, how much you are valued and the direction the whole relationship is taking.

Deep Questions to Ask Your Boyfriend


2. Who am I to you?

3. What are we?

4. Do you love me?

5. What is love to you?

6. Am I romantic?

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7. What is romance to you?

8. What makes me different from any other person out there?

9. How comfortable are you introducing me to your parents and siblings?

10. Would you like to see my parents and siblings?

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11. In your view, what will your mother think of me?

12. Do you wish to have kids soon? When is that and how many kids?

13. What makes you stand out above other people around you?

14. Do you think we would be together if you become a billionaire?

15. Do you have a best friend in life apart from your girlfriend?

16. What are you mostly misunderstood for?

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17. Who is your role model?

18. How much do you love me?

19. Do you think we have a future together?

20. How long was your longest relationship?

21. How short was your shortest relationship?

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22. When last did you have a serious relationship?

23. When was the first time you had sex?

24. Have you ever stayed with a partner for more than three months?

25. Have you married before?

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26. Have you ever been engaged?

27. Do you still remember where we met, how and what happened that day?

28. What is your view on the current political scene?

29. Will you vote this coming election?

30. What are you voting for?

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31. Tell me more about your dreams and aspirations in life.

32. What are you most afraid of?

33. Do you honestly think money can buy happiness?

34. To what extent can money buy love?

35. What accomplishments are you most proud of this far?

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36. What is the one thing you want to accomplish in your lifetime?

37. Do you have any addiction?

38. Have you ever used hard drugs before?

39. Are you introverted or extroverted?

40. What is your personality type in the 16 personality types?

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41. What do you do when mad at someone?

42. Do you hold grudges?

43. Have you ever been in a relationship you considered abusive before?

44. How likely are you to forgive cheating in a relationship?

45. Describe yourself in 3 words?

46. Which one word describes you the most?

47. Do you have a nickname? What is it?

48. How is your typical weekend?

49. What are you currently working on as far as a better future in for yourself is concerned?

50. What are your views on polygamy?

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Personal Questions to Ask Your Boyfriend

51. What do you do when feeling low?

52. What are your preferences between blue color executive job Vs. SME entrepreneurship?

53. Choose one between political career vs. business?

54. What is your favorite music?

55. What are your life values?

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56. Who or what inspires you the most?

57. What did you first think of me when we first met? Has anything changed since then?

58. What are your favorite memories of us so far?

59. What is in your bucket list for us this year?

60. What is the one thing you feel our relationship is lacking?

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61. What made you fall in love with me?

62. What are you most scared to ask me yet you want to know the answer?

63. What secret have you been wanting to tell me but often find it hard?

64. How would you love to receive affection?

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65. What is the biggest strength of our relationship?

66. What was your most vulnerable moment in our relationship?

67. What are your goals in this relationship?

68. What do you want the world to remember you for?

69. What habits do you find yourself struggling with right now?

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70. What is the most important lesson you have learned so far in regards to relationships?

71. What lesson have you learned t so far as life is concerned?

72. What is the most dangerous decision you have ever taken? How did it end?

73. If you have to change one thing about your past, what will it be?

74. What are the biggest lessons you learned from the previous relationship?

75. What are your thoughts on having a family in the next five years?

76. What is the worst gift you have ever received?

77. When young and growing up, what did you want to be? Did you try to achieve it?

78. What would you change in our relationship as it stands right now?

79. Who loves more in our relationship?

80. How much do you value me?

81. How much do you value our relationship right now?

82. Are we soulmates?

83. How would you prefer I express my love for you?

84. What secret haven’t you told me yet?

85. What have you wanted to ask but never found the right time?

86. What gets you frightened in our relationship?

87. What frightens you the most when it comes to love and relationship?

88. Are we compatible partners?

89. Have you been open with me so far?

90. Why did you fall in love with me?

91. What memory of us makes you smile instantly every time?

92. Do you believe in true love?

93. Do you believe in love at one sight?

94. Who is your hero? What qualities make your hero?

95. Would you rather be rich and lonely or be poor and be loved very much?

96. Who was your first girlfriend? What happened between you two?

97. How much has your life and relationship priorities changed over time?

98. What do you look for in a spouse?

99. What is your view on open relationships?

100. Do you think people should be close friends with their exes?

Love Questions to Ask Your Boyfriend

101. Do you have kids?

102. Have you ever gotten a girl pregnant?

103. Have married before?

104. Have you ever moved in with a partner?

105. Have you ever had a sugar mammy?

106. Have you ever been engaged?

107. Is money as important in a relationship?

108. Can there be love without money these days?

109. How would you describe your best friend?

110. Do you have female best friends I should be aware of?

111. What have you accomplished for this year?

112. How close are you with your former girlfriend?

113. What did you accomplish last year?

114. What is the weirdest thing you have heard people say about you?

115. Do you hold grudges sometimes?

116. Have you moved on from your former girl?

117. Should people be asking about body counts?

118. Do you have an addiction you are struggling with?

119. Have you ever had an addiction in your life?

120. What is the worst you have gone through in the name of love?

121. Have you experienced an abusive relationship before?

122. Can you lie if it will save the relationship?

123. How do you deal with negativity?

124. Why would a man cheat in a relationship?

125. How do you define loyalty in men?

126. Are you happy in your relationship right now?

127. When is the last time you were heartbroken?

128. What values do you want in your children?

129. What makes relationships last?

130. Have you had a friends with benefits type of relationship?

131. How many times have you been in love before?

132. What are you most afraid of in a relationship?

133. Do you love adrenaline activities?

134. How often should people be making out?

135. Are you hitting on someone else right now?

136. What do you like about your job?

137. How do you tell of someone is lying?

138. Do you prefer going out or staying in?

139. Where do you draw your inspiration from?

140. What are some of the sweetest lies you have ever told a girl?

141. What is the easiest way to win a girl?

142. In what ways have I changed since when we met?

143. Will you date me again if we are to meet in another life?

144. What makes me more desirable?

145. What is the worst you have ever thought of me?

146. Have you ever felt like I might be cheating?

147. How do you gain a man’s trust?

148. How often do you tell lies?

149. What is your next big thing?

150. Can I make a good mother to your kids?

Serious Questions to Ask Your Boyfriend

151. Have you ever fallen out of love?

152. Has a girl ever ghosted you?

153. What makes a lady a wife material?

154. What do you demand of your girlfriend?

155. What does commitment in a relationship look like to you?

156. Which books have shaped your thoughts a great deal?

157. Where do you see your life in the next 3 years?

158. What action are you least proud of?

159. When last did you shed tears and why?

160. What is the one thing you still regret about?

161. Do you like politics?

162. Do you have businesses or plan to set up some in the future?

163. How do you notice a wrong girl in your life?

164. How do you know when it is a bad influence?

165. Have you ever experienced a bad company influence?

166. Do you like spending time with me?

167. Is s#x such a big deal in a relationship?

168. What are your views on open relationships?

169. Are you into marriage or something else?

170. What is the one thing you like about me?

171. Who do you look up to for wisdom and inspiration?

172. What book are you currently reading?

173. What are you struggling with right now?

174. What is your life story?

175. Is this the life you pictured growing up?

176. How good are you are board games?

177. Which game are you good at?

178. How often do you work out?

179. Is dieting your thing?

180. What is your favorite watch brand?

181. What is your dream car?

There you have your complete list of deep questions to ask your boyfriend over text. Feel free to print your copy and have a blast the next time you meet.

Remember the deep questions to ask your boyfriend is a step toward understanding each other in a more meaningful way.

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