293 Questions to Ask Your Boyfriend in ANY Situation

Looking for the best questions to ask your boyfriend?

I know in a relationship you always look for emotional intimacy so you can strengthen the bond between you and your boyfriend. And why not its a thoughtful and excellent way to deepen the connection between partners to explore shared memories and emotions.

So if you want to deepen your connection with your boyfriend, then below we’ve compiled the list of best questions that you can ask your boyfriend that will spark your conversation and keep the flame alive in your relationship.

Scroll down and get ready to cherish memories together. Enjoy.

Questions to Ask Your Boyfriend

1. What’s your biggest hot take?

2. What is your most beautiful memory?

3. Do you like getting breakfast in bed?

4. What was your biggest adventure?

5. What was the best or strangest gift you ever got?

6. What’s your favorite part about being with me?

7. What’s the last thing that made you laugh?

8. Do fish have necks?

9. What’s the most American thing you’ve ever done? (Regardless of whether are American or not.)

10. How curious are you?

11. How do you like to express love?

12. What were some of your favorite childhood books?

13. What’s something you’re afraid to lose?

14. Tell me about your most embarrassing travel story.

15. What do I mean to you?

16. What do you like to do after work?

17. What’s the most memorable vacation you’ve taken?

18. Do you get jealous?

19. What great idea would you like to try if you had enough money?

20. What’s something I can do to make our relationship better?

21. What odd thing are you fascinated by?

22. What was the cleverest thing you did as a child?

23. What’s the best “who would win in a fight A or B” you can come up with?

24. Tell me your favorite travel story.

25. What quirks does your body have?

26. What’s your favorite memory we’ve made together?

27. Do I make you feel heard?

28. Who makes you uncomfortable when you are around them?

29. What website doesn’t exist but should?

30. What’s something you can’t live without? Why?

31. Did you ever sleep with stuffed animals?

32. Would you rather go out or stay in on a Friday night?

33. Which hairstyles fit with which personalities?

34. How soft are you?

35. What’s your favorite love song?

36. Tell me about your childhood crush.

37. How do you like to spend a rainy day?

38. What do you want to be written on your tombstone?

39. What’s your favorite song? Sing it for me!

40. What’s your worst vomiting story?

41. What’s a hobby you think we should try together?

42. If you started a podcast, what topic would it be on?

43. What’s your favorite holiday food?

44. What unique games or activities did you play as a child?

45. Where should our next vacation be?

46. What’s the best book you’ve read?

47. Have you ever told a joke and no one laughed? What did you do?

48. Do you prefer to stay home or go out on the weekend?

49. What inedible thing do you wish you could eat?

50. What’s the craziest conversation you’ve ever overheard in public?

51. Has a show or movie ever made you cry?

52. If jobs/careers had slogans what would be some of their slogans?

53. What seldom works the way it should?

54. What’s one fact no one else knows about you?

55. Do you have a pet? If not, would you ever want one?

56. How do you like to show love?

57. If colors had a taste, what would each color taste like?

58. What’s the last thing you Googled?

59. Have you ever used a pick up line? Was it successful?

60. What’s the craziest thing you’ve ever gotten the “ick” from?

61. If you could pick a theme song for yourself, what would it be?

62. What was your biggest travel mishap?

63. What makes you the happiest?

64. What are some of your family traditions?

65. What do you do when you feel stressed?

66. Do you think it’s possible to fall in love at first sight?

67. What have you stolen?

68. Do you believe in ghosts?

69. What’s the best conspiracy theory you can make up on the spot?

70. What is your favorite holiday?

71. Would you rather time travel or read people’s minds?

72. If you could live in any fictional town or city, which would you pick?

73. Are you an introvert or an extrovert?

74. If you had a pet tiger, what would you name it?

75. Do you think we have healthy emotional intimacy?

76. What’s legal but still feels illegal?

77. Who’s your celebrity crush?

78. Do you have any hidden talents?

79. What’s been the best year of your life so far?

80. What’s the plot of your favorite book?

81. Do you have a favorite plant or flower? If so, what is it?

82. Would you ever skydive? Why or why not?

83. If your loved ones didn’t approve of me, what would you do?

84. What makes you feel alive?

85. Can you think of two people in your life who have a relationship you look up to?

86. What’s the craziest thing you’ve done to impress someone?

87. What’s your favorite holiday?

88. How do I make you feel when we hang out with your friends?

89. What fictional character do you most identify with?

90. Do you believe in astrology?

91. Who’s your favorite person in your life?

92. Is there anything you wish you could change about yourself?

93. What’s a movie you can watch over and over again?

94. Tell me about your most memorable summer.

95. What’s your favorite movie theater snack?

96. What would your very own personal hell be like?

97. What was the most awkward moment you had at school?

98. What’s your most embarrassing moment?

99. What do you value most?

100. Do you believe in a higher power? Why or why not?

101. What’s your guilty pleasure?

102. Did you ever have a crush on a fictional character?

103. How did you feel the first time you saw your parents cry?

104. Do you think I’m living up to my potential?

105. What’s your love language?

106. Do you talk to yourself?

107. What’s your favorite holiday?

108. If you lost your job today, what would you do?

109. What’s the weirdest gift you’ve ever received?

110. How would you define falling in love?

111. If you could start a non-profit, what cause would you support?

112. What do you think is the weirdest habit you have?

113. Do you prefer city or country life?

114. What’s the best gift you’ve ever received?

115. When was the time you laughed the hardest?

116. If you have tattoos, which one’s your favorite and why?

117. What’s a hidden talent you have that you never get to show off?

118. Would you say you’re happy? If not, what can we do to change that?

119. Do you think we spend enough time together?

120. What’s your favorite part about being an adult?

121. When was the last time you voted?

122. What’s one thing we haven’t done yet that you’re excited to do with me?

123. What do you fear about the future?

124. What do you wish you had/hadn’t said?

125. What food or drink could you never live without?

126. How would the world change if health potions existed?

127. What creepy or cringey thing do you do on a regular basis?

128. What’s the biggest misconception people have about you?

129. What story involving you has probably been told by the most people?

130. What did you like to do during recess?

131. What’s your favorite city?

132. How lucky are you?

133. Did you love or hate P.E.?

134. Who or what is holding you back?

135. What are you a snob about?

136. How do you handle anger?

137. If you could be any animal, what animal would you be?

138. Describe your dream house.

139. What does self-care look like for you?

140. What’s your favorite thing about our relationship?

141. What’s the most uncomfortable thing you’ve had to tell someone?

142. What’s on your bucket list?

143. What are you really obsessed about?

144. What’s one holiday tradition you think we should start together?

145. What song could you listen to on repeat forever?

146. If you’re sick, do you want someone to care for you, or do you prefer to be left alone?

147. How much of the bad stuff that happens to you is your fault?

148. What’s your favorite scent?

149. Do you believe that every person has one soul mate?

150. What are you most passionate about in life?

151. What was the best sporting event you ever attended?

152. What bridges have you burned?

153. What does your ideal Sunday morning look like?

154. Have you ever traveled outside of the country? Tell me about it!

155. What event in your past has come back to haunt you?

156. What’s the hardest decision you’ve ever had to make in your life?

157. What should be the next advancement in shoes?

158. What’s your favorite pasta shape?

159. What actor would play you in that movie?

160. What word describes you better than any other word?

161. What brutally honest truth about yourself can you share with me?

162. How have you changed in the last five years?

163. Do you consider yourself an introvert, extrovert or ambivert? How has that impacted your life?

164. What’s something I do that annoys you?

165. Do you believe in aliens?

166. Where are you originally from?

167. What product are you shocked that no one has made a better version of?

168. Would you sacrifice your career goals for love?

169. What does your average work day look like?

170. How neurotic do you think you are?

171. What’s one movie you can watch over and over again?

172. What’s the hardest truth you’ve come to grips with?

173. What are your guilty pleasures?

174. What do people really need to chill out about?

175. What’s the most painful text you’ve ever received or sent?

176. Who’s the most surprising musical artist you love?

177. What candy do you think is overrated?

178. Have you imagined what our future house would look like?

179. Do you have a hidden talent?

180. What’s your favorite sport?

181. How well do you think you can read others’ emotions?

182. Do you ever feel like you lived a past life?

183. What makes you interesting?

184. What’s your biggest pet peeve?

185. What’s it like to be you?

186. Your most embarrassing moment?

187. What’s the craziest dare you’ve ever accepted during Truth or Dare?

188. How do you like to be treated when you’re sick?

189. If you started a cult, what kind of cult would you start?

190. How many places have you lived? What was your favorite place?

191. What sounds fills you with dread?

192. What scrambles your brain every time you think about it?

193. What’s the quickest way to make you angry?

194. What do you think aliens would actually look/be like?

195. What was your favorite subject in school? Did you have a favorite teacher?

196. What is the most alone you’ve ever been?

197. Do you believe in love at first sight?

198. What would you say is your best quality?

199. Do you prefer spontaneous or planned date nights?

200. If you could change your name, would you?

201. What’s the last book you read for fun?

202. In what situations do you act least like yourself?

203. What’s the most famous you’ve been?

204. How nurturing are you?

205. If you could go on any reality TV competition show, which would you pick?

206. What do you like to do on a rainy day?

207. Who’s your role model?

208. Do you like when I cook for you?

209. What about you scares you the most?

210. What do you get overly emotional about?

211. What’s the coldest you’ve ever been?

212. What is the kindest thing someone else has done for you?

213. What would you want your funeral to be like?

214. How do you feel about religion?

215. Do you prefer cooking for me?

216. What are some things you hid from your parents?

217. Where is the craziest place you have danced?

218. What’s the craziest thing you’ve ever done?

219. Are you a Valentine’s Day fan or hater?

220. Which celebrity would leave you starstruck in real life?

221. What was the best part of your day?

222. How did your parents impact your view on love and relationships?

223. If you could go back and relive any day of your life, which one would you pick?

224. What’s your morning routine?

225. Where is the most interesting abandoned place you’ve been to?

226. Have you ever had your heart broken?

227. Tell me about the worst first date you’ve ever had.

228. What’s your biggest fear? Do you think you can face it?

229. What mundane task have you mastered?

230. What is the kindest thing you’ve ever done?

231. What would make our relationship stronger?

232. Do I do anything that bothers you?

233. What’s your go-to karaoke song?

234. Are you friends with your coworkers?

235. Do you envision yourself having kids?

236. How do you feel about tattoos?

237. Tell me a funny story about your first car.

238. What event from the past do you most want to see a recording of?

239. What unnecessary products or services do you consider necessary?

240. What’s your favorite way to relax?

241. Have you ever met any celebrities?

242. What would your ex say is your worst quality?

243. How do you know when you’re really comfortable with someone?

244. What was your favorite toy as a child?

245. What’s the biggest risk you’ve taken?

246. What was the dumbest thing you said to a crush?

247. How often is your brain on autopilot?

248. Do I make you feel valued?

249. When you were a kid, what career did you want to have?

250. What do you wish you had more of growing up?

251. When did you know you were in love with me?

252. How do you fight off procrastination?

253. Are you allergic to anything?

254. What qualities do you think are most important in a spouse?

255. What’s your jam?

256. What’s the worst dream you’ve ever had?

257. What’s your comfort TV show?

258. When was the last time you were really, really wrong about something?

259. What does your perfect day look like?

260. Do you like being surprised by random gifts?

261. What is your happiest memory?

262. Do you play an instrument or sing?

263. What’s your favorite time of year?

264. Is there anything you’ve ever wanted to teach me?

265. What makes you happy? On the flipside, what makes you sad?

266. What’s the riskiest thing you’ve ever done?

267. What’s the last movie that made you cry?

268. What was your first kiss like?

269. What would it look like if you fully lived up to your potential?

270. What event made you mature as a person the most?

271. Do you prefer fancy or casual date nights?

272. What’s your favorite date we’ve ever been on?

273. What kind of parent do you want to be?

274. If there was a movie made about your life, what would the title be?

275. What qualities do you look for in a romantic partner?

276. What’s the cheesiest pickup line you’ve used on a crush before?

277. Have you ever kissed someone under mistletoe?

278. How do you want me to express love to you?

279. What does your ideal date night look like?

280. Are you a morning person or a night owl?

281. Do you sing in the shower?

282. What was your worst injury as a child?

283. What’s the grossest thing you’ve drunk?

284. Who’s your dream Super Bowl Halftime Show performer?

285. Do I show up in your dreams?

286. What’s a lame joke you use on a regular basis?

287. What keeps you up at night?

288. What was the best Halloween costume you ever had?

289. How did you spend your summer vacations?

290. Who is the nicest person you’ve ever met?

291. Do you like talking on the phone?

292. How much have you changed in 5 years?

293. What’s the strangest thing you’ve seen happen at a job you’ve had?

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