Let's Get Quizzical—350 Questions to Ask Your Boyfriend

Open up the conversation with these thought-provoking questions.

Each person's relationship needs will differ, but the best way to know, empathize and understand your partner's needs may just be to ask him. If you're looking to deepen your relationship with your beau, try starting with these 350 questions to ask your boyfriend that help couples connect. 

Unlike The Newlyweds game, the goal of these fun and romantic questions isn't to guess the answer or read your boyfriend's mind. It's totally okay if his answers surprise you; after all, everyone has a primary and then secondary love language, according to Psychology Today

But whether you're a new couple trying to get to know each other better or you've been in love for a while now, certain inquiries may help you forge a deeper understanding of what makes your partner tick. It could even lead to more openness, compassion and empathy between the two of you. Just sayin'.

350 Questions to Ask Your Boyfriend

1. How do you receive love and how do you give it?

2. Who do you trust the most?

3. What are you most passionate about?

4. What do you love most about our relationship?

5. At the end of your life, how do you want to be remembered?

6. What's your best attribute as a boyfriend?

7. What was your childhood like?

8. What are five scenarios in which you feel like you've succeeded?

9. What's your love language?

10. What's your favorite place in the world?

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11. What kind of qualities do you look for in a partner?

12. What qualities do you look for in a friend?

13. What does love mean to you?

14. What stresses you out the most?

15. If you could live in any country, where would you choose to live?

16. What's your biggest achievement?

17. How do you feel about aliens? Do you think they exist? What do they look like?

18. It's your last meal—what do you eat?

19. What do you consider beautiful?

20. What outfits do I wear that turn you on?

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21. What does your perfect day look like?

22. What's your favorite way to wind down after a stressful day?

23. What was your coming-of-age moment?

24. What is your dream job?

25. What's the funniest memory that sticks out in your mind?

26. What are you most grateful for?

27. What is your bucket-list country to visit?

28. What do you get most competitive about?

29. What's one life lesson that you think hasn't sunk in yet?

30. What turns you on?

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31. What's the most off-the-beaten-track food you've ever tried?

32. Who are your favorite women in power?

33. What do you think is your most controversial, unpopular opinion?

34. If you had all the money in the world, what would you do first and how would you live your life?

35. What are the causes you care about most?

36. If given the opportunity, would you go to space?

37. What's your favorite game to play?

38. In your favorite song, why do you think the lyrics speak to you?

39. Are you an extrovert or an introvert?

40. How do you like to impress someone you're interested in?

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41. What's your favorite outfit you've ever seen me wear?

Serious Questions to Ask Your Boyfriend

42. What kind of child were you?

43. Have you ever had a difficult time in your relationship with your parents?

44. What's a book you've read that stands out in your mind?

45. What do you consider your guilty pleasure?

46. How do you define cheating and have you ever been cheated on?

47. What's the most dangerous situation you've found yourself in?

48. Has there ever been a moment in which you were scared for your life?

49. What's your biggest pet peeve when dating?

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50. How do you feel about long-distance?

51. How much does playfulness matter to you?

52. Do you find yourself seeking validation?

53. How often do you find yourself on your phone?

54. What's one thing you've given up on?

55. What motivates you?

56. What's your favorite city in the whole world?

57. How do you feel about failure?

58. What does your dream home look like?

59. If money was no issue, what would you do in your day-to-day?

60. What makes you feel aligned with someone else?

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61. What does connection mean to you?

62. What's something extremely personal that is hard for you to share?

63. How do you feel about meditation?

64. How do you show others that you care about them?

65. How important is it to you what other people think?

66. What do you think you'll think about in the last moments of your life?

67. How do you protect someone you love?

68. If I killed someone, would you turn me in or help me cover it up?

69. What's your dream version of "community?"

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70. What was your dream or ultimate goal as a child that you've kind of buried away?

71. What do you consider yourself to be an expert in?

72. Do you thrive more with a routine or chaos?

73. Are you the person who packs for a trip the night before or is organized days/weeks/months in advance?

74. If money was no issue, what would you have been your major in college?

75. What's one habit that you can identify as harming you?

76. What do you think is inevitable?

77. What's one of your non-negotiables in a relationship?

78. What are some of the disadvantages of your job?

79. How important is owning a home to you versus renting?

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80. How do you most effectively take accountability for your actions?

81. What's something that feels unattainable to you?

82. What's a financial goal you haven't yet achieved but strive to?

83. What's your favorite family tradition?

84. What do you think you take for granted?

85. If your parents needed or wanted to as they grew older, would you consider taking care of them by having them move in?

86. What do you think your worst habit is?

87. Have you ever been in love?

88. Have you ever broken someone's heart?

89. How can you take on more responsibility?

90. How do you feel like you were raised?

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91. Do you feel evil is real?

92. If I chatted with your ex what would they say about you?

93. Who in the world do you feel closest to?

94. How do you feel about your family?

95. What is the way you show gratitude?

96. What makes you feel safe?

97. Where do you feel the safest?

98. How do you remember your grandparents?

99. What kind of employee are you?

100. What have you learned from your parents' relationship?

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101. Have you ever been arrested?

102. What can I do to make you feel most safe?

103. What are your views on polygamy?

Deep Questions to Ask Your Boyfriend

104. At their core, do you think people are good or bad?

105. What's the thing you regret the most?

106. How do you define vulnerability?

107. What comes easiest to you without much effort?

108. How do you feel about the current state of the world?

109. What's one thing I should know about you?

110. What kind of student were you in school?

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111. What was the most difficult life lesson for you to learn?

112. What is your favorite scent?

113. What's one ability you wish you could just have over night?

114. What's an obstacle in your life that changed your perspective?

115. Who do you go to when you need advice?

116. What do you fear the most?

117. Who do you go to who you know will tell you what you want to hear?

118. What do you find most challenging in your life?

119. What's your most irrational fear?

120. What are your feelings on horoscopes?

121. How do you feel like your astrological sign informs your decision?

122. What would you change about the world?

123. What kind of traveler of you?

124. What's your absolute dream job?

125. Do you have ideas about what you'd like to name your kids (if you want kids)?

126. How would you feel if we had a child with a disability?

127. Have you ever been in a fight with someone that got physical?

128. What do you expect the role of a "wife" or a "husband" to be?

129. How flexible are you with change?

130. What is your favorite memory of a person who's passed?

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131. How do you flirt?

132. How do I make you feel?

133. Do you live in a way that prioritizes your personal values?

134. As a child or teenager, which celebrity did you most idolize?

135. What makes you feel most connected to the world, the universe?

136. How would you like to impact the world?

137. Do you wear your heart on your sleeve or are you more pragmatic?

138. What's one belief that you think you'll never waiver from?

139. What makes you feel most alive?

140. What's one belief you had as a younger person that you've since abandoned?

141. Would you ever consider skydiving?

142. What was a time in which someone offended you?

143. What's a secret you hide from others?

144. What would happen if you showed a hidden part of yourself?

145. What makes you feel most grounded?

146. What does healing from past trauma look like to you?

147. What was the most standout compliment you ever received?

148. How do you tend to react to things: in anger or in empathy?

149. What does being a good partner mean to you?

150. Do you consider yourself an adventurous person?

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151. What are your feelings on divorce?

152. Do you consider yourself a defensive person?

153. What do you consider to be a boundary that shouldn't be crossed?

154. How good are you at keeping secrets?

155. How would you describe yourself as a friend?

156. How do you define loyalty?

157. What's the biggest, deepest life question you find yourself thinking about?

157. Do you consider yourself empathic?

158. Does empathy come easily to you?

159. What's your most shameful secret?

160. How do you feel about having serious conversations?

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Fun Questions to Ask Your Boyfriend

161. How do you define playfulness?

162. Who, if anyone, in your life have you learned to establish boundaries with?

163. What's something silly that gets on your nerves?

164. How do you prefer to load the dishwasher?

165. What kind of experience makes you feel loved?

166. What role does self-love play in your life?

167. What's one limiting belief you'd like to be free of?

168. How do you self-care?

169. What inspires you?

170. How do you put yourself first?

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171. If you had a journal, what would you write about?

172. What traits of your parents do you hope to emulate?

173. Are you honest with yourself?

174. What does it feel like for you to express your feelings: uncomfortable or easy?

175. In what ways do you think we are alike?

176. What parts of your own personality do you love?

177. What was an emotionally painful moment in your life?

178. How do you cope with adversity or pain?

179. How have you dealt with grief over someone you love?

180. What are you most hard on yourself for?

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181. Do you consider yourself a perfectionist?

182. What's one thing from your childhood you've had to unlearn?

183. In what aspect of your life do you feel the most pressure?

184. Do you think you are your friends' go-to person for advice?

185. What is most important to you in a marriage?

186. What are your feelings on soul mates?

187. How do you think we'd approach disciplining our kids?

188. What's your take on age differences in a relationship?

189. How often do you compare yourself or your life to others?

190. What's a topic that genuinely fascinates you?

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191. What do you think heaven looks like?

192. What motivates you to keep going and keep trying?

193. What do you feel guilt or shame about?

194. What's the most joyful part of your day?

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

196. What do you struggle with in a relationship?

197. What's your hidden talent?

198. How do you think you are with managing money?

199. What's your dream job?

200. How involved are you with your own family?

201. How do you define happiness?

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202. If we had kids, would you want me to stay at home or continue working?

203. Who played the most pivotal role in your childhood?

204. If you could pick anyone in your life to marry us, who would be your choice of officiant?

205. What "chores" do you hate doing?

206. What role do you want to play in our home dynamic?

207. What are your thoughts on politics?

208. Would you be supportive of my career goals?

209. Have you ever been in therapy?

210. Would you be open to going to therapy with me?

211. How do you show your love?

212. Do you consider yourself an affectionate person?

213. What's your take on splitting finances with your partner?

214. How do you handle arguments?

215. What kind of affection is important to you?

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216. What are you doing to be more eco-conscious?

217. What's a bad habit you once had that you've since kicked?

218. What do you think your parents would like about me?

219. How do you define self-discovery?

220. What's one area in which you recognize your own self-growth?

221. What did you most love to do as a child?

222. How have you attempted to break the cycles of your parents or family members?

223. Do you learn your lesson or do you keep making the same mistakes over and over?

224. What was the most magical part of your childhood?

225. How was your prom experience?

226. Where do you see our relationship going?

227. What's something extremely sensory you remember from your childhood?

228. What have you learned the hard way?

229. Would you rather say what you need to say or experience it alone?

230. What's the most difficult emotion for you to experience?

231. What makes you feel secure?

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232. What's one topic that is off-limits for you?

233. At what point in your life do you see yourself settling down?

234. How do you feel about couples therapy?

235. What's one thing you feel you've shifted your perspective on recently?

236. What, if anything, gives you anxiety?

237. What have you done, if anything, out of fear?

238. Have you ever experienced a panic attack?

239. How do you feel about physical intimacy?

240. At your core, what's your most important value?

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241. Have you ever lied on a date?

242. Have you ever lied to your partner?

243. How do you feel about marriage?

244. How do you feel about having kids?

245. What do you feel most pressure about?

Random Questions to Ask Your Boyfriend

246. In past relationships, were you the one who most often broke up with someone, or did you get broken up with?

247. Would you ever consider moving with me if I got a job opportunity elsewhere?

248. Where do you see yourself living in five years?

249. What's one professional accomplishment you haven't reached yet that's important to you?

250. At what point will you feel like you've made it?

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251. What does success mean to you?

252. What does your ideal relationship look like?

253. Are you a processor of information or a talk-about-it-right-now person?

254. If you had taken another path in life, where do you think it would have led you?

255. What activities make you feel most like yourself?

256. What do you think you and your ex butted heads about the most?

257. How honest do you want to be with each other?

258. Would you rather be truthful or hurt my feelings?

259. In the context of our relationship, what do you think you can do better?

260. What can you do to more meaningfully contribute to society?

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261. What keeps you up at night?

262. Are you a person that shuts down or do you prefer to talk things out until it's "fixed?"

263. How many relationships do you have?

264. Is it difficult for you to forgive?

265. What do you think your ex would say is your best quality?

266. Where is the most peaceful place you've ever been?

267. What sparks your curiosity?

268. What genuinely brings you joy?

269. How do you define bravery?

270. What's one thing someone's done to you that you struggle to forgive?

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271. What was the most monumental, life-changing moment in your life?

272. What do you excel at?

273. How are you with procrastination?

274. How important is it to be flexible in a relationship?

275. What does contentedness look like?

276. What's the most passionate disagreement you've had with an ex?

277. If you could relive one moment of your life again and again, what would it be?

278. What would you want to say to your future self?

279. How do you envision your life after retirement?

280. What does a meaningful life look like to you?

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281. What's your personal view on climate anxiety?

282. What's one way you feel you've really evolved in the past year? Ever?

283. What does being transparent mean to you?

284. Do you consider yourself an honest person?

285. What are your short-term goals and then your long-term goals?

286. How organized are you?

287. How messy are you?

288. How do you feel about vulnerability and expressing your feelings?

289. What's the biggest risk you've ever taken?

290. What's one moment in your life in which you just decided to "go for it?"

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291. How has your life changed in the last three months?

292. When do you find yourself most at peace?

293. What's your take on happiness?

294. Have you ever seen a psychic or would you be open to visiting one?

295. Do you believe in ghosts?

296. What makes you feel secure?

297. If you could be brought back to life after death, would you do it?

298. What does positivity mean to you?

299. Do you pray often? Or ever?

300. What's the kindest thing someone else has done for you?

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301. What is your relationship like with your parents now compared to a few years ago?

302. What area of your life have you neglected the most?

303. What's one habit you never want to break?

304. How do you ground yourself?

305. How important to you is sex?

306. What's the most embarrassing moment you've had with someone you were dating or in a relationship with?

307. Do you consider yourself to be a goal-setter?

308. What are you most proud of so far in your life?

309. What song or musical artist changed your life, if any?

310. Who do you consider to be your most influential mentor?

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311. How do you feel about getting out of your comfort zone?

312. What's your go-to karaoke song?

313. What's an area in which you feel the most confidence?

314. Are you hard on yourself?

315. Do you think you've forgiven yourself for your past mistakes?

316. What is the last book you read?

317. What's the most romantic vacation you could think of?

318. What do you consider to be "good" parenting?

319. How do you usually feel in social situations?

320. Do you tend to judge people by their physical appearance, even if subconsciously?

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321. What's your favorite way to spend a rainy day?

322. Do you find yourself experiencing intrusive thoughts?

323. Do you run hot or cold?

324. When was the last time you read a book?

325. Are you a good sleeper or do you suffer from insomnia?

326. Did you have a pet growing up?

327. Are you good at networking or is it hard for you to approach people?

328. What do you obsess over?

329. What's one activity during which you feel really connected with me?

330. Would you consider yourself a feminist?

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331. How many people do you consider to be true best friends?

332. Are you someone who forgets people’s names as soon as you meet them?

333. What's one thing you'd like to show me or teach me?

334. What's the hardest part about living with someone—either me or a roommate or even your family?

335. Have you ever stolen anything—even as a child or accidentally?

336. Who's your favorite celebrity and why?

337. Does anyone in your family suffer from addiction?

338. What do you find attractive physically?

339. What personality traits do you find most attractive?

340. What is the most monumental opportunity that you feel you missed out on?

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341. Have you ever won an award and what was it for?

342. What's the most romantic gesture to you that I could give you?

343. What's your opinion on the afterlife?

344. What's one aspect of yourself you think you could work on?

345. How do you think you would deal with fame?

346. How do you feel about fighting in a relationship?

347. What's the most effective way to resolve an issue?

348. Do you believe in God?

349. Do you believe in magic?

350. Is there anyone in life that you hate?

Next up, get to know your partner with these prompts.