Now Reading
500+ Deep Questions to Ask Your Boyfriend to Strengthen the Relationship

500+ Deep Questions to Ask Your Boyfriend to Strengthen the Relationship

Updated on May 18, 2022 | Published on October 14, 2021
Reviewed by Julianne Cantarella, MSW, LSW, Certified Relationship Coach
500+ Deep Questions to Ask Your Boyfriend to Strengthen the Relationship

Have you ever asked your boyfriend the deep questions? Well, your boyfriend had lived an entire life even before your arrival on the scene with many embarrassing moments, high achievements and broken relationships. 

In order to understand him better as well as his likes and dislikes, you have to know what deep questions to ask your boyfriend. Many of us often get swept up in the chaos and stress of day-to-day life. We got stuck in the same reputation of working, eating and sleeping. 

In this matter, it’s hard to ask to have some insignificant conversation with your boyfriend. This way you won’t regret it if someone asks you- how well do you know your boyfriend?

Not only understanding and finding out his trauma, regrets, passion and dream, but also to figure out the areas of improvement in your relationship and something that needs to be strong if you want to contribute in good times as well as bad times.

Therefore, here are more than 500 questions to ask your boyfriend right from funny, serious to intimate and personal. Whether you both are sharing a long-term or short-term relationship, these questions are the brilliant ways to begin the conversation, create bonding and get to know him better. 

500+ Deep Questions to Ask Your Boyfriend to Strengthen the Relationship
500+ Deep Questions to Ask Your Boyfriend to Strengthen the Relationship

Really deep questions to ask your boyfriend

Is your relationship getting serious? Then it’s time to know if you and your partner have the same values, want the same type of relationship and are willing to have the same kind of life. It’s useful to ask about his past issues and how he treated the relationship. 

Therefore, these necessary questions to ask your boyfriend help to find the answers you want and get to know him on a deeper level. 

1. What’s something that you are glad you will never need to do again in your life?

2. What would you do with a billion bucks if you were given it all at once?

3. What should people in a healthy relationship get out of it?

4. Do you believe that everything happens for a reason, or do we just come up with explanations after the fact?

5. Is there anything that you absolutely refuse to forgive?

6. What would you do first if you wake tomorrow without fear?

7. What has been the biggest benefit in disguise in your life?

8. Which year of your life would you like to get a do-over, and why?

9. What is one thing you will never put up with?

10. What three words would you write to your younger self if you could only write one?

11. What is it about you that makes you feel like you’re alive?

12. What’s something that you always procrastinate on?

13. What does your ideal day necessarily involve?

14. Do you follow your mind or hear while making any important decisions in your life?

15. What do you think will never end well?

16. If you would be able to change anything related to the way you were raised, then what would you like to change?

17. If you get a chance to live in someone’s body for a day then who it would be and why?

18. What are some of your excellent qualities that you admire a lot?

19. What is something in your life that you’re most grateful for? Is it family, job or career?

20. What are your long term wishes that you want to come true? 

21. What are the special qualities of your parents that you admire most and talk about often?

22. Is there anything that you want to change about yourself? Or, are you fine with who you are?

23. According to you, what is the right age to get married or when a person is ready for marriage?
24. What are some of the values that you want your children to possess?

25. What is one thing that people consistently misinterpret about you?

26. What is something that makes a relationship long lasting? Is it understanding, love, wealth or something else?

27. Are ambition and goals important in a relationship? If so, then why and what can you do to achieve them?

28. What is your biggest mistake in your life so far and what did you learn from that?

29. If your relationship or marriage life was taking a downturn then what would you do to save it?

30. What is something that helps you stay motivated during tough times?

31. Name one the person who is comfortable discussing anything about your personal and professional life.

32. Who is the one person or one thing you can lay down your entire life?

33. What is one thing that you want to achieve before you die?

34. If you get a chance to live forever, would you choose to live?

35. What is something that you are doing to improve world scenarios and why?

Deep conversation questions to ask your boyfriend

Getting to know your partner doesn’t need to be lighter. Therefore these deep conversation questions will shed some light on his adventures, favorite memories and personal values. Let’s get deeper into it. 

36. What is something you think to be real that no one else believes to be true?

37. What is your greatest life fear so far?

38. How do you calm down yourself in case of anger or panic? Any technique or tool?

39. What’s your favorite music and how does it make you feel?

40. What is the most emotional scene you have watched in a movie that made you cry?

41. Do you like to spend your time alone? What do you like to do when you are alone?

42. When do you have the feeling of being most alive? Can you tell me something about this?

43. What do you opt to ignore because it’s too difficult to bear?

44. What are some of the people that you enjoyed most when being around?

45. Do you feel that you are living your life to the fullest? If not, then why?

46. Is religion bad or good for work? What’s the impact of religion on people?

47. What is the biggest secret you have kept from someone?

48. What is the most important issue in politics or society that should be solved?

49. What has been the biggest change in your life so far that you have been most proud of?

50. What do you like to do for the people around you who you love the most in life?

51. When you hear the word home then what’s the first thing that comes to your mind?

52. If you want to go anywhere in the world right now then where would you like to be?

53. If you get a chance to travel back in time for one day then which year would you like to visit and why?

54. Do you think that there is something more in reality than what we see with our eyes?

55. Do you think that the universe is ever really meaningless? Or does it really have a purpose?

56. If you get a chance to erase the pain from your life then would you do that?

57. If you can give the date of year death then what would you want to know? 

58. If you could ask me one question and I had to answer honestly then what would you ask?

59. Would you like to live a short and exciting life or a long and boring but comfortable life?

60. What is the most valuable and memorable lesson that you have ever learned?

61. Are your priorities different these days than what they were in the past?

62. Would you be risky and single or broken yet deeply in love?

63. If you can get a tattoo right here right now then what would it be?

64. Do you think it’s important to be a nice person to everyone or only to friends and family?

65. Who are some of the people you could trust to live your life with?

66. Are you more comfortable hanging out with introverts or extroverts? And why is that?

67. Do you believe in destiny? Or do you think that we are the controllers of destiny?

Deep relationship questions to ask your boyfriend

When you are in a relationship for a long time then it can be hard to come up with new things to start the conversation. These interesting relationship questions are an excellent way to ensure that there will never be a boring moment between the two of you. 

68. What do you usually look for in a friendship?

69. Do you remember your long lasting friendships and how did it last so long?

70. Do you think that you can manage multiple best friends or only one is enough?

71. Do you think that your pet can also be your friend in case you don’t have one?

72. Do you consider your parents as your friend in some cases?

73. Do you think that opposite genders can maintain a friendship without building a love interest?

74. According to you, what is the unforgivable action?

75. What advice would you give to long distance friendships?

76. In your opinion, do you think that long-distance relationships can survive?

77. Do you think that a couple can split costs?

78. Do you think that it’s better to save money or invest in?

79. How can one divide the household chores to maintain a healthy lifestyle?

80. What do you look for in a partner or lover?

81. What is the most important thing in a relationship? Is it trust, respect or anything else?

82. Do you think that couples should argue or fight to maintain a healthy relationship?

83. What is the thing that comes to your mind when you first met me?

84. What is something that makes you super happy in a relationship?

85. When we initially started dating, how long did you imagine our relationship would last?

86. What is something that you are scared to ask me but want the answer too?

87. What is something that you really wish I did again and again?

88. What could be your perfect date night that feels special and memorable?

89. What are the three key elements that lead to a successful relationship?

90. If you were told to have a terminal illness then what would be the three things that you would like to do?

91. If you get a chance to live to 90 and have either the mind or body of a 30 year old then what would you choose?

92. What is a tradition that you did with your family and you want to continue this with your kids?

93. Would you prefer to surprise me with a pricey gift or would you prefer to speak with me before spending the money?

94. Do you believe a proposal should be a large public spectacle or a private intimate moment?

95. When we have children, what qualities would you want then to get from you and which from me?

96. What is something you did before but have regretted later?

97. What is something in life that you had to learn the hard way?

98. If you could go back in time to give advice to your younger self, then what would you like to tell?

99. What do you think is the biggest reason for the high divorce rate these days?

100. What is the biggest flaw of the welfare system?

101. What are some things in life that you want to learn the hard way?

Deep thought questions to ask your boyfriend

If you both love to talk about generous topics and thought provoking ideas, then you need some deep thought conversation questions to ask your boyfriend. Here is a complete list of questions which fall in this category to make him fall in love with you more while making eye contact. 

102. What is your favorite memory of dating me so far? And why is it?

103. What is your most favorite sexual memory of us?

104. Did ever any food remind you of me? If so, then which food?

105. When was the last time when you thought about me in a good way?

106. What is the most favorite thing that you love when I do it for you?

107. Which romantic movie reminds you of us and our love?

108. Which one of your parents do you like the most?

109. Which one is my best feature and you like it the most?

110. When was the last time you cried?

111. Do you ever feel jealous when you see me talking or waking up to other attractive people?

112. Do you ever dream about me? If yes, then what do you often dream about?

113. According to you, what’s the one thing that we need to work on the most in our relationship?

114. If you got sick then do you think that I would be there for you?

115. When you were a child, did you trust both of your parents?

116. What is the most special thing that I ever did for a special occasion for you?

117. Do you often think about me sexually during the day?

118. Is there anything I could do to increase your trust in me?

119. When do you often feel most protected and taken care of?

120. What can I possibly do to make sure that you feel safe and comfortable with me?

121. When we hang out with friends, then do you still feel that you are my priority?

122. When we visit our family, then do you still feel that you are my priority?

123. Do you know any deal-breaker things that can make you seriously reconsider our relationship?

124. What is the very first thing that you thought about doing for me?

125. Did you ever think that I am attractive? If so, then when you thought about it?

126. When it comes to having children, how long do you believe individuals should wait?

127. What is something that you learned from your parents’ marriage life?

128. What did you actually learn about physical affection from your parents?

129. When you were a child, what was your first favourite movie?

130. What do you want to do after getting retired? What’s your goal after retirement?

131. What’s another career that you think that you would love, apart from what are you doing right now?

132. What is your favorite physical feature of yourself?

133. Can you name your most favorite teacher when you were a kid?

134. Which significant other before me had the largest impact on you?

135. What did you think after having your first sexual experience?

Fun deep questions to ask your boyfriend

Sometimes, it’s quite hard to know what questions you should ask your partner and what not to let him know better. Therefore, here are some fun questions you can ask your boyfriend which will end up in laughing and bonding in no time. 

136. What was the weirdest reason you ever broke up with someone so far?

137. When was the last time you laughed the hardest till now?

138. If you get a chance of listening to only one song for the rest of your life then what would you like to choose?

139. Have you ever met any celebrities? If so, then when did you meet them?

140. Have you ever felt guilty of pop culture pleasure? If so, then what was that?

141. What was the most embarrassing thing that ever happened to you?

142. What is the weirdest thing that you ever bought for yourself or for your family and friends?

143. Have you ever visited a palm reader and did he predict the right thing about your future?
144. Who would you rather hire: a personal chef, a personal trainer or housekeeper?

145. What would you like to do if you could be a woman for a day?

146. What is the one movie that you have seen more times that you can count?

147. If a movie is being made about your life, then which actor would play your role? Which actress would play your love interest?

148. What were you like in high school? What was your personality at that time?

149. What fictional character do you relate to most of the time?

150. If you can be born in a different decade, then which decade would you choose?

151. Is there any favorite part about being an adult? If so, then what is it?

152. Have you ever played truth and dare? Then what was the most memorable dare that you accepted so far?

153. If you could be a superhero then what would your power be? 

154. When you fall asleep, then what do you prefer to be chilled and warmed?

155. If you got invited to lunch with a person who you have always wanted to meet then who is it?

156. What did you like the most? High school or college life?

157. What was the best party you ever went to and why did you enjoy it the most?

158. What is a question that you have never asked me and why?

159. Which of your personality characteristics would you like to change?

160. Have you ever gotten really obsessed with some topic or lesson?

161. When you needed to talk to one of your parents, who did you go to?

162. Which of your friends would you opt for if you had to be on a desert island with just one?

163. What do you think about couples who are married but live in different areas or cities?

164. What do you think about the couple who own a business together and spend all their time at once?

165. Which one do you like the most: a summer house, a boat or a year long vacation?

166. When you were a child, did you realize that you are fitted in perfectly?

167. Which one of your friends in your friend group is the funniest?

168. Do you think that I have a good sense of humor?

169. Do you like to have some funny conversations when you are upset or in a bad mood?

Deep love questions to ask your boyfriend

Communication is an important aspect of any relationship. If you don’t ask about your relationship and love often and where it’s going then it might lead to problems over time. Therefore, here are top questions to ask your boyfriend about love and connect with him deeper. 

170. What would you do if you had an extra $1,000 to spend on yourself only?

171. Did you ever feel like you belonged as a child?

172. In middle school, what was your favourite subject?

173. Did you go through puberty first, second, or third, or at the same time as everyone else?

174. Who was your first love interest?

175. When you were younger, who was the first person you kissed?

176. When was the first time you had a crush on someone?

178. Do you consider yourself to be more of an introvert or an extrovert?

179. What age would you be if you could go back in time?

180. What would you want to know if you could see into the future?

181. What is your most valuable skill?

182. What is your most distinguishing feature?

183. What distinguishes me from the other folks you’ve met?

184. What is the most positive aspect of our relationship?

185. Do you ever find yourself comparing yourself to other men or women?

186. Which of my pals do you consider to be the most entertaining?

187. Do you consider yourself an optimist, pessimist, or realist?

188. What do you think about when you wake up in the middle of the night?

189. What would you alter about yourself if you could only change one thing about yourself?

190. Do you believe I’m a realist, an optimist, or a pessimist?

191. Did you ever rebel against your parents when you were a teenager?

192. In your extended family, who is the person closest to you?

193. Have you ever wished for a sibling with more or fewer siblings?

194. What role did your siblings play in shaping who you are today?

195. Which of our date nights was your favorite?

196. When you see me at the end of the day, what are your hidden thoughts?

197. Do you think that I will ever be able to read your mind and when?

198. What are things about me that make you know that I am the one for you?

199. When was the last time you said “I love you” to someone who wasn’t a family member?

200. When did you go on your first date, and where did you go?

201. Describe the most romantic date you can think of, and don’t skimp on the details!

202. What questions would you ask if you were on a dating game show?

203. What is your favorite recollection of our time together?

204. What do you hope to get out of your time with me?

205. Which would you prefer: a luxurious penthouse suite or a private beach house?

Deep meaningful questions to ask your boyfriend

Your partnership might have great stories and ideas that you have never heard of because you both never talked about it so far. Therefore, here are some meaningful questions about your relationship and other things around you. Let’s have a deeper look into it. 

206. Do you want to have children and if so then how many?

207. How long was your last relationship and what was the reason for ending it?

208. Have you ever gotten married or engaged so far? If not, then do you ever want to get married?

209. Have you ever loved a partner and how was your experience with this?

210. How much importance do you give to your religion or Spirituality in your life?

211. How do you feel about homosexual rights? Do you think that it is right?

212. Do you think that materialistic things can buy happiness if relationships and careers do not?

213. Do you have any dream job? If so, then what is it?

214. What is the one thing that you want to achieve in your life and why?

215. Which one of your accomplishments do you feel most proud of?

216. How do you like to describe your relationship with your family? Is it good or average?

217. Have you ever struggled with addiction? If so, then what was that addiction?

218. Have you ever been involved in an emotionally or physically abusive relationship?

219. Do you think that any relationship can come back even after cheating?

220. Who was your role model while growing up?

221. When you were a kid, what career did you want to opt for and why?

222. What is your ideation for a perfect Sunday afternoon that you enjoyed the most?

223. What is the best gift or present that you have received so far? And why did you like it?

224. What did you and your friend usually do in middle school for having some fun?

225. If you could cook any dish perfectly then what would you like to choose?

226. When you are having a bad day then what makes you feel comfortable and better?

227. If you want to visit an amusement park then what ride do you want to go on often?

228. What is one of the toys that you always wanted as a child but no one ever bought for you?

229. Did I ever sleep with stuffed animals and how did you feel there?

230. What are your favorite scents out there? Can you tell me about it?

231. Which one is your favorite karaoke song and why did you like it so much?

232. What is your favorite activity to do during recess or break?

233. What is your favorite activity to do on rainy days? Eating, resting or anything else?

234. Which fictional character do you have a crush on and why so?

235. Have you ever pranked anyone so far? Have you ever been pranked?

236. If you can eat only one food for the rest of your life then what three would you choose?

237. If you can trade places with one person for a day then who would it be?

238. If you can inhabit any movie, TV show, book or another financial universe then where would you live?

Deep questions to ask your boyfriend about himself

People love to talk and disclose stuff about themselves if asked in the right way. And so your boyfriend is. If you wanna show him that you care about him more than you and want to understand him better for a healthy relationship, then here are some of the deep questions to ask your boyfriend. 

239. Have you ever had a romantic relationship?

240. Who was your first love interest?

241. How did your first kiss go?

242. Is it more necessary to have an emotional or physical connection in a relationship?

243. Whose relationship do you admire the most among your friends and family?

244. What is the most crucial quality in a spouse for you?

245. When you think of me, what is the first thing that springs to mind?

246. What is the most enticing outfit for a partner to wear?

247. What kind of date would you like to go on?

248. What’s a Halloween costume for couples that you’ve always wanted to try?

249. Would you relocate for the sake of your partner?

250. Do you have any souvenirs from previous relationships that you keep? (Greeting cards, letters, photos, and gifts)

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

252. Have you ever kissed someone who was kissing you beneath the mistletoe?

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

254. What do you enjoy most about dating?

255. Do you believe in the concept of fate?

256. What is the most significant sacrifice you’ve ever made for the sake of a relationship?

257. What is your favorite song about love?

258. What is your favorite aspect of our friendship?

259. What is one thing I can do to improve our relationship?

260. Do you enjoy spending time with my friends and family?

261. What am I doing that makes you feel valued?

262. Are you content with the emotional closeness we share?

263. What can we do to help each other out more?

264. Are we positively influencing each other?

265. Is it possible that we’re enabling each other’s unhealthy habits?

266. What should I focus on more? What should I cut back on?

267. Do we communicate enough when we’re not together?

268. What is your favorite memory from our time together?

269. What kind of journey do you want to do together?

270. What is a pastime or talent that you would like to learn as a couple?

271. Do you believe we fight in a fair manner?

272. Is there anything that you always wanted to tell but never got the guts to talk about?

Best deep questions to ask your boyfriend

Are you looking for the best deep questions to ask your boyfriend? Then, here you go. Here is the complete list of good questions you can ask your significant other to know him better and strengthen your bond, bring you closer and intimate at a higher level. 

273. Do I make an appearance in your dreams or fantasies?

274. Which day from our relationship would you choose if we could relive it?

275. Do you consider yourself a jealous person often?

276. When was the last time you felt frightened? How did you handle it?

277. What are you most proud of having accomplished in the previous year?

278. What were your life’s big turning points?

279. When was the last time you pushed yourself past your limits? What was your reaction to it?

280. What is the happiest memory you have?

281. What has changed about you in the last five years?

282. When was the last time you sobbed, and why did you cry?

283. What has been one of the most essential life lessons you’ve learned?

284. What is the most audacious thing you’ve ever attempted?

285. What has been the most important lesson you’ve taken away from previous relationships?

286. What has been the most difficult setback you’ve ever faced? How did you get through it?

287. What would you change about history if you had the chance?

288. Which song would you choose if you had to listen to only one of the songs you loved as a kid for the rest of your life?

289. Did you have any pets as a kid?

290. In five years, where do you see yourself?

291. What do you think our future holds for us? What direction do you think it’ll go?

292. What are your relationship objectives?

293. What are your feelings about starting a family?

294. What are some of the things on your bucket list that we can cross off this year?

295. What is the one thing you most want to accomplish before you die?

296. Do you want to change any of your habits?

297. What part of growing older do you most look forward to?

298. What do you hope to gain knowledge on in the future year?

299. What is the best piece of advice you’ve ever received?

300. If you can see the future one time then what would you like to see first?

301. Would you alter anything about the way you live now if you knew you would die abruptly in a year? Why?

302. Tell your partner about a time in your life when you were embarrassed.

303. Your house catches fire, destroying all you own. After you’ve saved your loved ones and pets, you have enough time to make a last-ditch effort to preserve any one object. What would it be, exactly? Why?

304. What is your favorite Halloween costume to wear to a party?

305. Is there anything you’ve wanted to do for a long time? Why haven’t you gone ahead and done it?

Deep dark questions to ask your boyfriend

Not asking secretive and dark questions might make your relationship boring. Therefore, if you want to add some fun and excitement then dark questions are a way to choose. Let’s deep dive into the possible dark questions to ask your boyfriend right away. 

306. How many times did you change your mind about your profession before deciding what you actually wanted to do?

307. Do you have a deeper relationship with your mother or father? What makes you think that?

308. When you were a child, who was the first person you fell in love with?

309. What are five words that come to mind when you think of yourself?

310. What about the future terrifies you the most?

311. Do you believe you could be a good parent? Why do you think that is?

312. What is anything you will take away from the way your parents raised you if/when you become a parent?

313. And what is one thing you will never change about the way you were raised?

314. Are you a believer in the afterlife? Why do you think that is?

315. What is one thing you wish you hadn’t compromised on in a relationship?

316. In a relationship, what is anything you refused to compromise on that you wish you had?

317. What would your closest friends say about you?

318. What would your old buddies think of you now that you’ve grown apart?

319. Do you believe that love is something you can’t control or something you make a conscious effort to do?

320. Have you ever done anything wrong?

321. What is your biggest worry about the future?

322. What motivates you to get out of bed in the morning?

323. What do you consider your most egregious blunder?

324. What are your coping mechanisms for dealing with stress?

325. What keeps you from going after the things you really want?

326. Is there anything about yourself that scares you?

327. Do you believe that sexual compatibility or emotional compatibility is more important in a relationship?

328. Describe your worst/hardest break up.

329. Do you believe we can fall in love with someone for the rest of our lives?

330. Do you believe in staying friends with your exes? Why or why

331. Have you ever had to get rid of someone who was poisonous in your life? How did you pull it off?

332. When you’re upset, where do you go?

333. Can you tell me about one of your biggest strength and regret?

334. Do you believe we only have one soulmate in this life, or do we have several?

335. Do you believe your younger self would be proud of who you are today if they met you today?

336. Who would you invite to dinner if you could invite anyone in the world?

337. Do you ever practice what you’re going to say before making a phone call? Why?

338. For you, what would an ideal day look like?

Deep intimate questions to ask your boyfriend

Intimacy is the one of the most essential parts of any relationship, however, sometimes we feel distant in the intimate moment in our life with our partner. In order to reconnect with your boyfriend on an intimate levels, here are intimate questions to ask your boyfriend to make your bond with him better and deeper. 

339. How many times would you have sex in a week in an ideal world?

340. What’s something you’ve always wanted to try in bed but never got around to it?

341. Have you ever had a threesome? Would you ever have one?

342. Have you ever felt compelled to pursue a man?

343. What happened to your virginity?

344. When did you first get into the habit of masturbating?

345. What’s your most cherished sexual fantasy? Do you think you’d do it in real life?

346. Outside of the bedroom, where do you prefer to have sex?

347. Have you ever been followed during a sex session? Have you ever stepped into a room and found someone else there?

348. What is the most bizarre request you’ve ever received in bed? Are you the one who did it?

349. Who would you invite to dinner if you could invite anyone in the world?

350. Do you want to be well-known? What do you mean by that?

351. Which would you choose if you could live to be 90 years old and have the intellect or body of a 30-year-old for the last 60 years of your life?

352. Do you have a sneaking suspicion about how you’ll pass away? (If they have the same dark sense of humor as you)

353. What one attribute or ability would you get if you could wake up tomorrow with?

354. What would you want to know if a crystal ball could tell you the truth about yourself, your life, the future, or anything else?

355. What are your thoughts on porn? What kind of pornography do you enjoy?

356. Which sexual position is your favorite? Which sexual position is your least favorite?

357. What are the most sensitive erogenous zones on your body that don’t always get the attention they deserve? (Nipples, ears, neck, and so forth.)

358. What portion of sex do you enjoy the most? (Examples include foreplay, teasing, penetration, oral sex, pillow chat, and so on.)

359. Who would you like me to dress up as if we were going to role play?

360. Have you ever gone to a dominatrix? Would you ever go to one?

361. What’s the one sex item you’ve been itching to try?

362. What is the strangest thing that makes you happy?

363. What aspects of your childhood would you change? What aspect of your childhood would you never change?

364. Have you ever succeeded in getting someone pregnant? How did you deal with it?

365. What is one aspect of yourself that you wish you could change?

366. Have you ever been caught cheating on someone? Have you ever been duped by someone?

367. What’s the biggest mistake you’ve ever made?

368. What is the most common misunderstanding about you?

369. Have you ever had to call off a friendship with a friend?

370. Do you keep in touch with any of your ex-boyfriends or girlfriends?

371. What is a terrible habit that you would like to get rid of?

Deep personal questions to ask your boyfriend

Some romance to your relationship starts with knowing personal things about your partner. Your partner probably has several personal experiences that you have never talked about. No worries! Here are the deep personal questions to ask your boyfriend on a romantic day? 

372. Which would you choose if you could live to be 90 years old and have the intellect or body of a 30-year-old for the last 60 years of your life?

373. Do you have a sneaking suspicion about how you’ll pass away?

374. Name three things that you and your partner seem to share.

375. What would you alter about the way you were raised if you had the chance?

376. Take four minutes to tell your partner as much about your life as you can.

377. What one attribute or ability would you get if you could wake up tomorrow with?

378. Have you ever spied on a friend or a partner?

379. Where would you like to live if you could live anywhere? Do you want to live on a farm in the middle of nowhere, an attractive mansion by the river, or a trendy city condo?

380. When you retire, what do you want to do?

381. What kind of trip would you like to take? Traveling to Maui for an all-inclusive resort, London for sightseeing, or Yosemite National Park for camping?

382. What would you choose if you could have any skill without having to work for it?

383. Do you believe that men and women can simply be friends?

384. When you’re sick, how do you prefer to be treated? Do you like to be served on or to be left alone?

385. Do you suffer from any phobias? (Spiders, heights, germs, and other dangers, for example.)

386. What is your most annoying activity so far?

387. What is a cause that you are passionate about that you have volunteered for?

388. What would you start a charity for if you were to start one?

389. Do you follow the news on TV, read it in the newspaper, or listen to it on the radio?

390. What is the best piece of advice you’ve ever received?

391. Do you enjoy conversing on the phone?

392. What are the stumbling blocks in your relationship?

393. What is something you want us to do together on an island?

394. What would you study if you had to go back to school?

395. So far, what has been the happiest memory year of your life?

396. When was the last time you said “I love you” to someone who wasn’t a family member?

397. When did you go on your first date, and where did you go?

398. What is your favorite feature of mine?

399. Do you think real love exists, or do you believe in love at first sight?

400. Do you believe that people are meant to be together?

401. What is the ideal honeymoon destination?

402. Describe the most romantic date you can think of, and don’t skimp on the details!

403. What questions would you ask if you were on a dating game show?

404. What do you hope to get out of your time with me?

405. Which would you prefer: a luxurious penthouse suite or a private beach house?

Deep questions to ask your boyfriend over text

Texting is the new era to connect and have a deep conversation. Therefore, why not take some advantage of it for your relationship. While chatting with your boyfriend you can ask some deep thought questions to know your partner better. 

So, here is the desired list of questions to ask over your text with your boyfriend. 

406. What will you choose between money and love? And why?

407. How do you imagine a completely perfect relationship? And why so?

408. Does your name contain any specific meaning? If so, then what is it?

409. How do you cope with people that deliberately irritate you?

410. Tell me about something you’ve never told anyone in your life.

411. What is the most ridiculous reason you’ve ever given for not going out?

412. Have you ever been unlucky in love? What went wrong?

413. What have you taken away from your previous relationship(s)?

414. What is one thing that people believe you are but aren’t?

415. What is one of the most bizarre pick-up lines you’ve ever heard?

416. What is something that you have been mistaken for what you are not? What was it and how did you go about it?

417. What is the most nice thing that I ever said to you and you liked it the most?

418. What is something that your parents will be surprised to know about you?

419. How can you tell someone when you liked them like a friend vs when you like them more than as a friend?

420. What is the most adventurous place you have visited and wanted to go there again?

421. Have you thought and are tired of making the first move to someone whom you liked?

422. What was my impression on you? Has anything changed since then?

423. Would you rather be known for being so smart or being so sexy?

424. Are you a reserved person or do you express your feelings most of the time?

425. What is something that most people don’t know about you?

426. Do you have something that most people won’t believe about you if you told them?

427. What do you think that most people find strange and weird?

Deep romantic questions to ask your boyfriend

Asking deep questions can develop a strong bond between both of you and bring you closer to each other like never before. 

Romantic questions can be ideal for you to continuously improve the relationship and stay loyal to each other if there is something that needs to change. 

We have created a comprehensive list of romantic questions to ask your boyfriend to develop an intimate bond between you and him. 

428. If you can travel to the past? If so, then where do you want to travel? 

429. What is your ideal dream location for a vacation to enjoy with your family? 

430. If your paycheck could be a number then what would your career like to be?

431. Do you prefer dogs or cats as pets? Do you want one as a pet in the near future?

432. Where do you want to spend your life if you had to choose to stay in one place for the rest of your life?

434. If you get a chance to learn an instrument to play then which one would you like to play and why?

435. What is your favorite task to do in your free time? Would you like to do the same with me?

436. Where do you want to have your first apartment or home? Do you want to stay there for long?

437. If I have to describe you in three words to my friend then what three words should I say?

438. When you are having a bad day then what usually cheers you up?

439. What is your favorite place to go for a lunch meeting? Would you like to visit there with me? Which romantic music puts you in the mood there?

440. What should be the next romantic movie which you and I should watch out together?

441. Which one is the most impactful and romantic book that you have ever read? Would you also recommend that book to me?

442. If you get a chance to return to a year in your past life and want to restart your life from that age, then which age would you like to return to?

443. What is something that you struggle to share with people about yourself but you want to share with me?

444. Is there any biggest fear about the future? If so then what is it?

445. What is your most favorite memory of us together? And what about when we have been distant?

446. Which one of your parents do you find the most in your own personality? 

447. When was the last time you got angry at someone or something?

448. Is there anything that you want to change and evolve in our relationship?

Deep serious questions to ask your boyfriend

Want some seriousness in your conversation? Here are top questions to ask your boyfriend when you both want to have some serious talk about your relationship, past life, future plans, family and other life issues. 

449. What superpower would you choose if you had one?

450. Do you believe that flying or mind reading is a more useful ability?

451. What human talent would you choose if you could have one that you don’t have now?

452. What three wishes would you make if you had three? (excluding any further wishes)

453. What would you fix if you had the power to fix one problem in the world?

454. What would you do if you could teleport to any location on the planet?

455. What animal would you be if you could be for a week?

456. What would you be if you could be an object for a day? 

457. What would you order if you could eat everything you wanted right now?

458. What planet would you like to visit if you were to go to the farthest reaches of the universe?

459. What would you do on your last day if the world ended tomorrow?

460. Would you prefer to travel back in time to witness dinosaurs or travel forward in time to see our futuristic society?

461. Which book or film would you make a reality if you had the chance?

462. Who would you choose if you could be a character from a popular television show?

463. What is the one aspect of our relationship that you would miss the most if it ended?

464. Do you believe you’ve exposed yourself to our relationship?

465. When we were dating, what do you believe was your most vulnerable moment?

466. Do you believe I’ve exposed myself in our relationship?

467. When we first started dating, what do you think was the funniest moment?

468. What is one feature about me that I consider a weakness but that you adore?

Deep sexual questions to ask your boyfriend

Being sexual is one of the important parts of a relationship. Not just with the actions but words also do magic to arouse both of you. 

If your sex life is going to be boring and not so exciting anymore then here are top sexual questions to ask your boyfriend for maintaining your sex life and relationship in a long run.

469. What method of orgasming with a partner do you find to be the most reliable?

470. When I come down on you, what do you appreciate the most?

471. When you’re masturbating, what do you think about?

472. Would watching porn together turn you on?

473. What do you think about a threesome?

474. What is a sexual act you have never tried but would like to?

475. Do you have any fetishes, fancies, or kinks you’d want to share and/or engage in?

476. What kind of role play would pique your interest the most?

477. Which obscene words irritate you the most?

478. What would you want to do to me if we agreed to do whatever we wanted to each other? So, what exactly would you like me to do to you?

479. Do you prefer to be the boss or the follower?

480. How do you feel about anal play?

481. Do you have any sexual memories you’d like to share with us?

482. Do you have any sex-related anxieties or reservations?

483. What are your feelings on our sex lives? What should we focus our efforts on?

484. What adjectives would you use to characterize your sexual desires? Is it more kooky or more vanilla?

485. What aspect of our connection do you believe we should improve?

Random deep questions to ask your boyfriend 

If you want to have some conversation starters then here is the relevant list to ask random questions in order to interact and spend quality moments for a long time. 

During a conversation or at the start of the conversation, you can ask these questions to have a joyful and long interaction with your partner.

486. Is it more important to you to have good looks or to have good brains?

487. Would you ever forgive someone who had cheated on you?

488. Do you mind if your password is shared with your partner?

489. Do you believe a person is ready for marriage at a certain age?

490. How do you envision yourself as a parent?

491. What would you do if your parents didn’t approve of your relationship?

492. Who is the one person with whom you can chat about anything?

493. What’s your favorite movie to watch on a dating night?

494. Would you rather do the romantic dishes or cook a romantic dinner?

495. When do you believe it is appropriate to express “I love you”?

496. Do you believe that arguing in a relationship is beneficial or should be avoided?

497. What is one thing you’ve learned from another marriage that you think is important?

498. Men or women, do you believe, have it tougher?

499. Who do you believe is the most attractive person you can think of?

500. Could you describe the menstrual cycle and why it occurs to me?

501. Could you perhaps explain why the sun appears to rise and set?

502. Do you believe the term “once a cheater, always a cheater” is accurate or false? Have you ever cheated on someone?

503. What is your opinion of Elizabeth Warren and why?

504. What is the most flattering dress you’ve ever seen me in?

505. Do you believe I’m more successful in my career or in my personal life?

506. Do you prefer to be a stay-at-home or working parent, and why?

507. Do you like the notion of someone putting dinner on the table for you every night at 6 p.m.? Why do you think that is?

Bottom line

There is not any particular limit when it comes to deep questions to ask your boyfriend. It will also tend to be thought provoking conversation that can make your bond stronger. 

You can ask these questions as a starters while presenting a romantic gift or dinner, so jot down the surprising things you can find out about your parents using these questions.

You don’t need any specific time to start with this, just when both want to have some deep conversation then this is a way to go. Whether you both are sharing a quick meal or cuddling before bed, you can take advantage of that time to connect on a deeper level. 

No matter what your relationship status is, asking these deep questions will help you strengthen the bond, intimacy and romance. 

Without a second thought, grab your partner and have some memorable experience on a deeper level.