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200 Fun Questions to Ask Your Boyfriend

A photo of Tom who is the Co-Founder of Questions About Everything

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Struggling to think of questions to ask your boyfriend? We’ve compiled a list of questions that will ensure you won’t run out of talking points.

If you’ve been in a relationship for a while, it can be hard to find new things to talk about with your boyfriend. If that’s you, then these questions for your boyfriend should help.

There’s a wide variety of topics covered here. From questions about your relationship, questions about their life goals and favorite things, we’ve included some random questions to ask your boyfriend too!

With this list, you’ll have hours and hours of talking points lined up with your boyfriend that you can use to have some fascinating conversations!

Questions To Ask Your Boyfriend List

question to ask your boyfriend about whether they'd like to be a father someday
  1. Do you want to be a father someday?

2. Do you think you only truly get to know your partner when you live with them?

3. Do you think it’s possible to repair a relationship if someone has cheated?

4. What’s an intimate fantasy you have that you haven’t been able to act out yet?

5. Whose relationship do you admire the most out of your friends and family?

6. What’s the strangest reason you broke up with someone?

7. What has been the most dramatic change of mind you’ve ever had?

8. Do you think that physical intimacy is as important as emotional intimacy?

9. What do you think is the most important trait in a partner?

10. What’s the best thing you’ve learned from a relationship, good or bad?

11. How much do you miss me when we’re apart?

12. Is there a conspiracy theory that you actually secretly believe could be true?

13. What would I have to do that would make you end the relationship without discussion?

14. Is there a conspiracy theory you think might actually be true or at least partly true?

15. Do you aspire for our relationship to be like your parents or not? In what ways yes, and in what ways no?

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16. What’s the most embarrassing thing that’s ever happened to you?

17. What’s one activity you’re eager to do together as a couple?

18. What first attracted you to me?

19. Is there anything I do that secretly annoys you?

20. Stereotypically, girls are more bothered about the wedding day being perfect but is there anything you specifically want at yours?

21. Have you ever broken up with someone for reasons you now feel were silly?

22. What’s something you’ve always wanted to tell me but don’t have the courage to mention?

23. Who’s your weirdest celebrity crush?

24. What do you remember the most about the first time we met?

25. If you had to describe me in three words, what would they be?

ask your boyfriend what three words they would use to describe you

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26. How long did you think our relationship would last when we first started dating?

27. Do you have any close female friends? Do you think that’s normal or strange?

28. What was your longest relationship? What happened that it ended?

29. Do you believe there’s someone you’re ‘meant to be with?’ Or is love more random than that?

30. What part of my character do you like the most?

31. What do you think of marriage?

32. Who have you ever lived with – friends, family, or partners?

33. How much money is too much? Can a certain amount of money make you happy? Can too much make you sad?

34. If you could live and work anywhere in the world, where would it be?

35. If you saw someone crying, would you ask them if they were OK? Why and would it depend on who it was?

36. What does masculinity look like in your mind?

37. What’s your love language, as in how you feel most loved?

38. What happened when you were a child that made you grow up quickly?

39. Have you ever had a run-in with the police? What’s your opinion on the service?

40. What’s a ridiculous thing you are able to do? Impressions? Put your feet behind your head? Put your tongue on your nose?

41. What was the best day of your life?

42. Who’s your best friend? Who’s your closest friend? Are they the same?

43. What’s your family dynamic like? Does everyone get on with one another?

44. If you had to choose between video games or TV and movies for the rest of your life, which would you choose and why?

45. Do you worry you’re addicted to anything, even things people (might) find socially acceptable? e.g. Caffeine, smoking, porn.

46. If you could give one message to the people of the world, what would you say?

47. Do you need guidance on anything right now?

48. If you had to perform on stage, what would you do?

49. What’s the craziest random encounter you’ve ever had?

50. Who brings out another side of you? Do you like this side?

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51. If you could make it that you never had to sleep, would you? How would it affect you psychologically?

52. If you had unlimited money, what business would you like to start?

53. What daily task do you hate the most?

54. If you could only visit one place on holiday for the rest of your life, where would you go?

55. Who was your biggest role model when you were a child?

56. What was the best holiday you’ve ever been on?

57. What’s the best gift you’ve ever gotten?

58. If you have had pets, which was your favorite?

59. What did you and your friends get up to when you were young?

60. How would you improve a normal household appliance that you find annoying?

61. What would you love to do or achieve that no one has done yet?

62. What do you enjoy doing that others find is a waste of time?

63. If you found out you had a secret half-brother or sister, would definitely want to reach out to them? What would stop you?

64. What’s your biggest fear?

65. What’s a big thing you’ve never told your parents?

66. Do you cry a lot? What would make you weep?

67. What most annoys you about yourself?

68. What’s one item you would buy if money was no object?

69. Are you excited or scared about the future?

70. What’s the most difficult thing you’ve had to accept about your life?

71. What’s the thing you most want to do before you die?

72. In what ways does society look down on men?

73. Is there anything you continue doing even though it rarely, if ever, works?

74. What have you never told me, that you’ve always wanted to, but never had the opportunity?

75. What do you feel you’ve missed out on in life?

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76. Have you lived through the best part of your life already?

77. Who do you need to be around to feel the most like you?

78. Do you find it easy to blame things on others, or do you more readily blame yourself?

79. When have your expectations for something been too high? When have they been too low?

80. What do you wish you could learn with just a click of your fingers? If realistic, why don’t you put time into learning it?

81. What was your most embarrassing moment?

82. If you could live in another time period, which would you choose and why?

83. When has someone found out something about you that has been incredibly embarrassing or inconvenient?

84. Do you feel you’re different around different people? Why is that?

85. How’s being an adult different from how you expected?

86. What would you do if you were a woman for the day?

87. What fictional character do you see yourself in?

88. How would you like to die?

89. What’s your opinion on procrastination? Is it a good or bad thing?

90. What are you most interested in?

91. How would you change yourself physically, if you could?

92. Are you easily swayed by others’ opinions, or are you very firm in what you think?

93. When do you feel most alone?

94. Do you enjoy spending time with others or on your own the most?

95. How aware are you of others’ feelings?

96. What are you most confident in yourself about?

97. Where do your values or morals come from?

98. Do you have an obsessive side? What do you obsess over?

99. Are you OCD about anything? Do you check the door is locked more than once or have to have the volume on an even number on the TV?

100. Do you enjoy taking risks or playing it safe?

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101. What’s your overall opinion of social media?

102. What gives your life meaning? Is there a central meaning of life for all?

103. What was the biggest life-changing decision you’ve ever made?

104. When have you been in the most pain, either physically or emotionally?

105. Is there something you did in your past that you would change if you could?

106. What made your upbringing unique?

107. What would make the best day off for you?

108. What’s the strangest job you’ve had?

109. Have you ever had a near-death experience? What happened?

110. Have you ever done something illegal?

111. What’s the biggest risk you’ve ever taken?

112. What’s the manliest you’ve ever felt?

113. What place in the world most scares you?

114. Who have you lost touch with and wish you hadn’t? Why did you?

115. What do you remember from your childhood that scared you?

116. What do you most envy about someone else’s life?

117. What do people think about you that just isn’t true?

118. What was the hardest break-up you’ve been through?

119. Is there anything in your life that you feel you need to talk to a phycologist about?

120. Have you ever met a celebrity? What happened?

121. What’s your worst habit? What’s a habit you’re proud of?

122. Is there such a thing as a white lie? Is it ever ok to deceive?

123. What’s the most difficult thing you’ve ever had to do?

124. Does your mind wander a lot or do you find it easy to focus?

125. What was the worst day of your life?

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126. Do you have any memories that you shudder about when you remember them?

127. Who in life has hurt you the most? What did they do?

128. What do you think of the term ‘mankind’, and what do you think of the term ‘humankind’?

129. What was the most awkward situation you’ve ever been in? Did you make it awkward or was it someone else?

130. Have you ever been in love before?

131. Who was the first girl you fancied growing up?

132. What’s the worst thing you’ve ever eaten?

133. Who in life do you most look up to?

134. How could I show you more love?

135. What’s the best date you’ve ever been on?

136. Is your best friend now your best friend from when you were a child? What happened to your first one if so?

137. Are you close with your cousins, uncles, and aunties?

138. What’s the biggest embarrassment that’s happened in your friendship circle?

139. Who do you struggle with the most at work?

140. What’s the greatest thing your parents have passed on to you?

141. Do you know anyone who you find you start acting or speaking like when you spend lots of time with them?

142. What’s the greatest prank you’ve pulled on someone?

143. When has someone completely surprised you in their opinions, actions, or what they’ve said?

144. People say that the first year of marriage is the hardest – why do you think this is?

145. What’s something silly you couldn’t live without?

146. Do you think that men and women have different roles in marriage?

147. What about others gets you the most frustrated?

148. What do you struggle with being in a long-term relationship?

149. What was your healthiest relationship?

150. What couple do you aspire to be like?

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151. Who are two friends you never thought would make a good relationship, and yet somehow it works?

152. If we could go anywhere together right now, where would you want to go?

153. In what ways were you fed an idealized picture of love and relationships when you were young? How has it affected your love life?

154. What do you love about being in a long-term relationship?

155. Is there a foreign language that makes you attracted to someone if they speak it?

156. What are your career goals?

157. What unobvious thing can make someone more attractive to you?

158. If it was needed, would you go to a marriage counselor or would you be too prideful?

159. Is there something other couples have done or do that you think is impossible for us?

160. What’s something you can do for hours on end without getting bored?

Serious Questions To Ask Your Boyfriend

161. Do you think people need to change themselves before they start trying to change the world?

162. What’s your greatest daily headache?

163. Who’s the greatest human being to have ever lived?

164. What was the best age you’ve ever been?

165. What’s your favorite historical event?

166. Are there any friendship groups or groups of any kind you are a part of that you don’t feel fully accepted in?

167. Have you ever kept a diary?

168. What do you think was your most vulnerable moment in our relationship?

169. What negative emotion are you most inclined to feel?

170. What’s your most inspirational quote, saying, or verse?

171. What do you find the most relaxing?

172. If I said you could date other people, would you?

173. When in your life have you had to ask for forgiveness or is this something you do all the time?

174. What’s a common skill that you think is being forgotten by most?

175. What part of being in a relationship is overrated?

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176. What did you learn at school that you later found out was false?

177. What’s the best piece of advice you’ve given someone else?

178. How would you describe your life in a few short sentences?

179. Have you ever had the desire to join the army, navy, or air force? Could you do it if you had to?

180. What’s the scariest thing you’ve ever had to do?

181. What has been said about you that has stayed in your mind for many years and affected you deeply?

182. What was your biggest waste of money?

183. Who do you most look up to?

184. Who in your life do you argue with the most and why?

185. What will your grandchildren not be able to believe about your childhood?

186. If I surprised you with an activity we could do together, what activity do you think I’d choose for us to do?

187. How would you solve homelessness?

188. What’s your favorite way to receive affection?

189. What do people accept in society that we really shouldn’t?

190. What do you find great meaning in that others think is a waste of time?

191. How can I show you love more?

192. Is there something you used to buy regularly but for some reason you don’t anymore?

193. Where’s the most beautiful place in the world?

194. What superpower would you choose?

195. Have you ever tried fasting from food? Do you think you could do it?

196. If you had a YouTube channel, what would it be called and what kind of videos would you release?

197. Are there any ways we’re having a bad effect on one another?

198. What do you see yourself doing with your time when you retire?

199. Do you prefer talking on the phone or texting? Why do you think that is?

200. Is there an evening class you’d like to take together, or if we had to, what would you choose?

Looking For More Questions?

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A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.