250 Questions To Ask Your Boyfriend

When a relationship is new and fresh it’s a fun time of exploration and discovery. And we don’t just mean in the bedroom. The initial months of dating a new partner are an exciting time when you get to ask all the questions and find out as much as you can about the new prospective love of your life. This is the period of time when you can ask hard-hitting questions and go below the surface and really find out what the person you are dating is all about, especially if you are a woman.

As we know, men aren’t always the most talkative, so if you can get them chatting early you will have more understanding of them and what they want from the relationship. To make sure you are on the right track, we’ve come up with a list of questions to ask your boyfriend that will give you a great insight into their personality. 

While these questions are designed for people who are in the early stages of dating, they can also be handy for those in long-term relationships. You can never not know enough about your significant other and these questions will help keep the lines of communication open so you are both heading in the same direction. 

250 Questions To Ask Your Boyfriend

Fun Questions 

Start things off with a fun question or two to break the ice. You might hear a few funny stories and it lightens the mood before you go in for the kill with serious questions that might lead to a deep conversation between you both. 

1. What is the craziest thing you’ve ever done? 

2. Have you ever lived overseas? 

3. What is your funniest travel story? 

4. Have you ever traveled outside of the country?

5. What do you always procrastinate doing?

6. Nightclub or pub?

7. What is your favorite movie/band/book?

8. If you could travel anywhere in the world right now, where would you go and why?

9. What are your guilty pleasures? 

10. Do you have any family traditions? 

11. What was your favorite subject in school? 

12. Do you have any pets? 

13. What is your favorite food?

14. What is the best gig you’ve ever been to? 

15. Do you play sports?

16. What is the best sporting event you ever attended?

17. Have you ever sung karaoke? If so, what’s your go-to song? 

18. Do you prefer to stay at home or go out on a weekend?

19. What is your favorite fast food?

20. What is your favorite holiday destination?

21. If you had to listen to one song on repeat for the rest of your life, which one would you choose?

22. What is the dumbest thing you have ever done?

23. Who is your favorite superhero and why? 

24. What is the strangest gift you have ever been given? 

25. Who would play you in a movie? 

26. What is your favorite city? 

27. If you could have any superpower, what would it be? 

28. What is your favorite thing to do when you are relaxing?

29. If you had all the money in the world, what would you spend it on?

30. Boxers or briefs? 

31. If you could have a conversation with anyone, dead or alive, who would it be?

32. Who is your celebrity crush?

33. What is your most embarrassing moment? 

34. What gets on your nerves? 

35. Have you ever broken the law? 

36. Who do you think should pay for dates? 

37. How do you feel about surprises? Do you like to be surprised?

38. When you’re having a bad day, what makes you feel better?

39. Do you have any hidden talents? 

40. What is your favorite dessert? 

41. What is the best Halloween costume you have ever worn?

42. What is a book or movie you’ve always lied about having read or seen?

Deep Questions

Having a meaningful conversation about your hopes and dreams and views on life is important. Asking a deep question or two means you can get past the small talk and really find out what makes a person tick. 

43. What do you think is our purpose in life?

44. Are you a spiritual person? 

45. Does religion play a role in your life?

46. What’s something most people don’t know about you?

47. When did you last lose your temper?

48. How do you feel about gay rights?

49. What are your biggest flaws? 

50. What is your best quality? 

51. Can money buy you happiness? 

52. What are you doing to care for the planet? 

53. Is it ever ok to lie?

54. What is your dream job? 

55. When do you most feel loved and how? 

56. What makes you angry? 

57. What is something that most people underestimate or overestimate about you?

58. Who do you think has it harder: men or women?

59. Do you have any annoying habits? What are they? 

60. What is one thing you want to accomplish in life before you die?

61. Are you close with your family?

62. What stresses you out? 

63. What makes you the best version of yourself? 

64. What is your favorite memory from childhood?

65. Would you rather be a stay-at-home parent or a working parent and why?

66. Who is the person in your life you can always count on?

67. What is your passion project? 

68. Which way do you lean in politics? 

69. What is a weakness in other people that bothers you?

70. Who do you go to for advice? 

71. What do I mean to you?

72. Do you hold grudges?

73. What can you not live without? 

74. How have you changed over the years? 

75. What is the most significant thing you have done in life?

76. If your family and friends didn’t approve of me, what would you do? 

77. Have you ever struggled with addiction? 

78. How do you handle conflict? 

79. What is something you’ve always dreamed of doing but never have?

80. Do you think you will be a good dad?

81. What inspires you? 

82. Where is your favorite place on Earth? 

83. How do you define success? 

84. What do you think makes a good man?

85. Are you a jealous person? 

86. When was the last time you cried? 

87. Where do you see yourself in five years? 

88. Do you believe in second chances? 

89. What do you care about in life? 

90. Do you think it’s possible for men and women to just be friends?

91. What scares you in life?

92. Do you have any regrets? 

93. What is your relationship like with your parents? 

94. Have you ever been to therapy? 

95. What do you want to be remembered for? 

96. Do you have a best friend? 

97. What triggers you? 

98. What is the best piece of advice you have been given? 

99. Have you ever had to break up with a friend? 

100. Would you rather be right or happy?

101. What do you want to do when you retire? 

102. Have you ever gotten anyone pregnant? How did you handle it? 

103. What was the hardest decision you’ve ever had to make? 

Cute Questions

Conversation starters like cute questions will make you both feel warm and fuzzy inside. 

102. What makes a cute couple?

103. How can I help you when you have had a bad day?

104. What is the most romantic thing you have ever done? 

105. What is your favorite memory of us? 

106. Do you believe in soulmates? 

107. What is your love language? 

108. Favorite childhood memory?

109. What was something about me that attracted you at first sight?

110. Who and when was your first kiss? 

111. What is the kindest thing you have ever done? 

112. How often do you think about me?

113. Did you ever sleep with stuffed animals?

114.  Is there any song that instantly makes you think about me whenever you hear it?

115. What is your favorite thing about me? 

116. If you could only describe me in one word, what would it be?

Relationship Questions

Ask an interesting question about your relationship or your boyfriend’s past dalliances and find out whether he is the one. While we don’t claim to be relationship experts, these questions are great for finding out more about your partner’s past relationships and what they want from your current one. 

117. Do you want to have children? 

118. How long was your longest relationship? Why did it end?

119. What would your ex-girlfriends say about you? 

120. Have you ever had a long distance relationship? 

121. Are you still friends with any of your ex-girlfriends? 

122. Have you ever been engaged or married?

123. Do you keep mementos from past relationships (Cards, notes, photos, gifts)?

124. What does love mean to you?

125. What’s something you’ve done but will never do again, no matter what?

126. Do you ever want to get married?

127. How long should people date before meeting their parents? 

128. How can we make our relationship stronger?

129. Do you believe in love at first sight?

130. Have you ever lived with a partner?

131. What do you think is most important to have in common with someone you’re dating? 

132. How do you like to show love?

133. How do you like to receive love? 

134. What do you think makes for a healthy relationship? 

135. Have you ever been in a toxic relationship? What happened? 

136. How many women have you said ” I love you” to? 

137. What is the biggest thing you’ve taken away from your past relationships? 

138. Are you a good communicator in a relationship? 

139. How do you show love in a relationship? 

140. When you break up with someone, how do you go about it? 

141. How would you handle another guy hitting on me? 

142. Do you think we have defined roles in our relationship? 

143. Have you ever been cheated on?

144. What are your thoughts on public displays of affection? 

145. Have you ever cheated on someone? 

146. What are some of your relationship red flags?

147. Where do you see our relationship going? 

148. What does your ideal date night involve? 

149. If one of my friends flirted with you, would you tell me? 

150. What is the most ridiculous thing you’ve ever done to impress someone?

151. What do you expect from your partner? 

152. How many times have you had your heart broken? 

153. How can we support each other more? 

154. Would you prefer to cook a romantic dinner, or do the romantic dishes?

Flirty and Filthy Questions 

It doesn’t have to be all serious and cute questions. Juicy questions about what you like between the sheets are also good questions that reveal a person’s sexual side. Some are harmless fun while others might make you blush. 

155. What is the best way to give you an orgasm? 

156. How many sexual partners have you had? 

157. What can I do to improve our sex life?

158. How often would you like to have sex? 

159. What is your favorite way to have sex? 

160. What is your dirtiest sexual fantasy?

161. Where’s the weirdest place you’ve had sex?

162. Do you use any adult toys, and if so, what ones?

163. Have you ever sent nudes to someone? 

164. Are you interested in pegging? 

165. What is your favorite physical feature about me? 

166. Have you ever had a threesome? 

167. What is your biggest turn-on in the bedroom?

168. What is your biggest turn-off in the bedroom?

169. Have you had sex in public? 

170. What age was the oldest person you have had sex with?

171. What is the age of the youngest person you have had sex with? 

172. How often do you masturbate? 

173. Do you prefer to be dominant or submissive?

174. Have you ever been caught having sex? 

175. What do you fantasize about when you masturbate? 

176. Have you ever had anal sex, and if not, are you willing to try it?

177. Do you watch porn? What type of porn and would you watch with me? 

178. When was the last time you had a dirty dream?

179. At what age did you lose your virginity? 

180. What is the most sex you have had in one day?

181. Do you enjoy dirty talk? 

182. What is one sexual act you have always wanted to try but have yet to do so? 

183. Have you ever made a sex tape? 

184. What is your best or most funny sexual experience? 

185. Do you prefer morning or evening sex?

186. Have you had sex with multiple partners in one day?

187. Are you into BDSM?

188. Do you like being tied up during sex?

189. Do you prefer rough or gentle sex?

190. What are your thoughts on the swinger lifestyle? 

191. Do you like your toes being sucked?

192. Have you joined the mile high club?

193. Do you fantasize about other people when having sex? 

194. Are you dominant or submissive in the bedroom?

195. Have you ever played strip poker?

196. Do you like shower sex? 

197. What is the longest you have gone without having sex?

198. Have you ever used handcuffs during sex?

199. If you could have sex with any famous person, dead or alive, who would it be?

200. Would you have sex on camera for money?

201. If we were going to role play, who would you want me to dress up as?

202. Have you ever paid for sex?

203. Do you enjoy dressing up in the bedroom?

204. Have you ever been walked in on during sex? Have you ever walked in on someone else?

205. What is the wildest thing someone has asked you to try in the bedroom? 

206. Have you ever had sex with another man? Is that something you are interested in?

207. What are your most sensitive erogenous zones that don’t always get attention? 

208. Do you like watching me masturbate? 

209. Have you ever/would you ever go to a dominatrix?

Random Questions

Here is a bunch of questions about all manner of subjects and topics that you can throw into a conversation and see what sticks. They cover a wide range of things and make for some interesting chats. 

210. What was the last movie that made you cry?

211. Do you snore? 

212. What did you want to be as a kid? 

213. If you were a flavor of ice cream, what flavor would you be? 

214. What kind of animal would you be? 

215. How would your friends describe you? 

216. Which cartoon character best represents you? 

217. Do you have any irrational fears or phobias? 

218. What movie have you seen the most? 

219. If you could eat only three foods for the rest of your life, what three would you choose?

220. What is the most important thing in the world to you? 

221. Do you prefer to eat out or cook for yourself? 

222. What are your favorite smells? 

223. Who would you rather hire: a personal trainer, a personal chef, or a housekeeper?

224. What was your childhood nickname?

225. Have you ever met a celebrity, and if so, who? 

226. Do you believe in conspiracy theories? Which ones? 

227. What would you do if you could be a woman for a day? 

228. What is your favorite thing to do on a rainy day? 

229. If you could change your name to anything, what would you pick?

230. Do you believe in ghosts or spirits or have any paranormal experiences?

231. What came first, the chicken or the egg? 

232. What is the worst drink you have ever had?

233. If you were asked to vacate your residence immediately, which five things would you take with you?

234. What vegetable best describes who you are? 

235. Do you have any funny nicknames from childhood?

236. Which fictional character do you most relate to? 

237. If you could trade your life with someone for a day, who would it be and why? 

238. What were you like in high school? 

239. Have you ever broken any bones?

240. If you had to pull a prank on someone, what type of prank would you pull? 

241. When did you last laugh the hardest? 

242. If you could be born in a different decade, what decade would you choose?

243. Would you try drugs even if they were legal?

244. Have you ever stolen anything? If so, what? 

245. If you find a large sum of money on the ground, what will you do?

246. What would the title of your autobiography be? 

247. Do you believe in aliens? 

248. Have you ever peed in a swimming pool? 

249. What are some of your favorite memories of going to an amusement park?

250. If you had three wishes, what would you wish for?