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510 Deep Questions to Ask a Guy for Deep Conversation

510 Deep Questions to Ask a Guy for Deep Conversation

Updated on Jul 01, 2022 | Published on Nov 22, 2021

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

510 Deep Questions to Ask a Guy for Deep Conversation

Do you think that you know almost everything about a person but you would still like to dig deeper? Or, you are only getting to know someone but you are wanting some challenging and interesting questions to get to the bottom of who they really are?

Then, deep questions to ask a guy are the right way to go. 

The greatest method to actually learn what is behind their surface and develop a sense of trust between you both is to ask him another personal tough and insightful question.

Apart from this, it can be a fun experience to discover a side of someone you might never have seen before.

Most people get why from the deep stiff and as a result, most connections are surface level and superficial at best. Going deep is the only way to truly connect and get to know someone.

These questions range from personal to interesting. Some may find out painful memories or some others are mind-benders that are just interesting to think about.

If you want to connect with him deeply, then these questions can help you to take it to the next level. Let’s get deeper into these questions.

510 Deep Questions to Ask a Guy for Deep Conversation
510 Deep Questions to Ask a Guy for Deep Conversation

Deep personal questions to ask a guy

Deep questions are the direction to deep conversation.

If you are someone who loves a guy and wants to establish a deep-hearted conversation with him then you definitely need a list of personal questions to ask a guy

If you both have known each other for a long time and are comfortable talking on various personal and confidential topics, then here is the right set of more than 20 questions that you can use as conversation starters for small talk or to spice up your conversation. 

1. Is poverty a natural outcome of human society?

2. What do you actually constitute a wasted life?

3. Who was the one person who single-handedly transformed the path of human history?

4. Which of the following events would you rather die than witness?

5. Do you believe morality is a human construct or does it exist in nature?

6. How would the ideal version of you look?

7. What is the most important objective to which a person may devote their life?

8. What has had the most significant influence on your political views?

9. Why is depression such a taboo subject in our society?

10. What is it that prevents people from understanding themselves?

11. Why do some people continue in toxic relationships even when they know it’s bad for them?

12. What are three jobs that machines will soon be able to take over?

13. Will technology be humanity’s savior, downfall, or neither? Why?

14. What human characteristic is presently beneficial but would have been harmful in the past?

15. What are we doing now that will be considered primitive and backward in a century?

16. Do you believe humans will survive long enough to evolve into something new, or will we go extinct before we get the chance?

17. Should the government, the elderly’s family or the elderly themselves be responsible for their care?

18. Is human awareness simply the flow of electrons through neurons, or is it something more?

19. Should we test babies for psychopathic or sociopathic characteristics if we have the ability to do so? 20. What should we do with babies who are on the approach of becoming psychopaths?

21. Is it necessary to address income inequality? If not, what is the reason? If that’s the case, what are some effective and realistic ways to close the income gap?

22. Why do people do actions that they know are harmful to themselves and others?

23. How would you be judged if everyone’s life was measured by whether they had a net good or negative impact on humanity?

24. What is the single most effective action a government might undertake to improve the lives of its citizens?

25. Would you choose yourself if a machine could completely duplicate your mind, right down to the same pattern of synapses firing? Could it tell you how you’d react in any given situation? Why do you think that is?

26. If you could invite anyone in the world to dinner, who would you invite?

27. Do you aspire to be famous? What exactly do you mean?

28. Before making a phone call, do you ever prepare what you’re going to say?  Why?

29. For you, what would a perfect day look like? What is your day-to-day activity?

30. When was the last time you sang to yourself? To whom are you addressing this?

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

32. Do you have a strong feeling about how you’ll pass away?

33. Identify three things that you and your partner appear to have in common.

34. In your life, what do you feel most grateful for?

35. What would you change about the way you were raised if you could?

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

37. Is there something you’ve been wanting to do for a long time? Why haven’t you gone ahead and done it?

38. Would you alter anything about the way you feel alive now if you knew you would die suddenly in a year? Why?

39. Share anything about your relationship that you think is good quality. Five items total should be shared.

40. Is your family close and welcoming? Do you believe you had a happier childhood than the majority of people?

41. What is your opinion of your mother’s connection with you?

Deep questions to ask a guy over text

Deep conversation is most comfortable and deep as ocean over text.

So, if you are looking forward to some fun light-hearted conversation with your boyfriend and getting personal information about your boyfriend or crush then here is the list of more than 21 questions to ask a guy or girl over text. 

42. Make three “we” statements that are true. “We’re both in this room feeling…”, for example.

43. “I wish I had someone with whom I could share…”, complete the phrase.

44. If you and your partner were to become close friends, please tell them everything they need to know.

45. Tell your partner what you admire about them; this time, be completely honest, stating things you wouldn’t say to a stranger.

46. Tell your partner about a time in your life when you have an embarrassing moment.

47. When was the last time you shed a tear in public? Is it true that you’re on your own?

48. Tell your lover (already) something you admire about them.

49. What is too serious to be joked about, if anything?

50. What would you most regret not telling someone if you died tonight evening with no opportunity to contact anyone? Why haven’t you informed them?

51. Your house catches fire, destroying all you own. After you’ve saved your loved ones and pets, you have enough time to make another last effort to save anyone object. What would it be, exactly? Why?

52. Which member of your family’s death would be the most upsetting to you? Why?

53. Share a personal issue and seek help from your partner on how to deal with it. Additionally, have your partner reflect back to you how you appear to be feeling about the situation you’ve chosen.

54. What three wishes would you make if you could?

55. When you were a kid, who was your favorite cartoon character?

56. To you, what does spirituality imply? Have you ever transmitted cached or otherwise? 

57. Do you believe in second chances, and if so, why?

58. What would you say was the first time you had a crush?

59. What are some of your favorite pastimes?

60. What zodiac sign do you belong to? Do you believe in astrology as well?

61. What would you like people to remember about you after you’ve passed away?

62. What was the most valuable lesson you took away from a previous relationship?

63. Which books are some of your favorites? Can you suggest one for me?

64. Have you ever experienced a revelation? If so, how did it go for you?

65. What has been the most intense experience you’ve ever had?

66. What would you do with your life if you had a big dream?

67. Do you prefer the morning or the evening?

68. Do you believe anyone can cheat, or do you believe only cheaters cheat?

69. Have you ever been caught shoplifting?

70. Have you ever made a mistake that you later came to regret?

71. Do you ever justify your negative behavior? (For example, I punched him in the face because he was a jerk.)

72. What are your thoughts on artificial intelligence (A.I.)? Is it terrifying or incredible?

73. What are your thoughts on Elon Musk?

74. How do you feel about Steve Jobs? Are you a hero or a villain?

75. What do you think the best way to deal with climate change is?

76. Do you believe that psychics are truly psychic?

77. What is your preferred method of exercise?

78. What do you think you would be like if you grew up in a different family?

79. Have you had your heart broken before? How did it make you feel?

80. What kind of music makes you feel energized?

81. Are any of your high school friends still in contact with you?

Good deep questions to ask a guy

Good things make life better. Therefore, here comes the need for good deep questions. If you are someone who is quite desperate to have a deep as well as good conversation, then we have got you covered.

Below is the list of questions that you can ask your loved one during a great conversation or spending good time together. 

82. In high school, what was your favorite subject or class?

83. Can you tell me about your strangest childhood memory?

84. When you’re stressed, how do you unwind?

85. What is the talent you want to improve?

86. If you could go back in time and modify one decision you made as a child, what would it be and why?

87. If you could change one thing about your childhood, what would it be and why?

88. Do you know how to play any musical instruments?

89. What is one accomplishment that you’re proud of?

90. What three non-electric or non-automatic items would you take on a deserted island?

91. If you had the power, what would you alter about yourself?

92. What is your preferred mode of public transportation? (By air, boat, train, bus, or vehicle, for example.)

93. What is the most daring thing you’ve done recently?

94. Which two radio stations do you listen to the most in your car?

95. Would you hire someone to help you with cleaning, cooking, or yard chores if you had the money?

96. Which would you prefer to visit: Mexico or Alaska, and why?

97. What is your favorite aspect of your job?

98. Where would you live if you could live anywhere?

99. What is the proudest achievement of a member of your family?

100. What would you do if you had the freedom to do anything for a day?

101. What is the best gift you’ve ever received?

102. What would you do if you had the freedom to do anything for a day?

103. Would you want to win the lottery or have the ideal job? And why is that?

104. Have you ever been referred to by a nickname? What exactly is it?

105. If you won the lottery, what would you do with the money?

106. Are you a fan of or scared about surprises? Why do you think that is?

107. Which do you prefer: riding a bike, horseback riding, or driving a car?

108. Would you prefer to play a game, see a relative, watch a movie, or read in the evening?

109. What is your favorite sport or game to watch and participate in?

110. What would you eat if you could only eat one meal for the rest of your life?

111. Which would you like to do: clean the house, mow the grass, clean the bathroom, or wash the dishes?

112. Do you want to win the lottery or work towards the perfect job?

113. On a deserted island, who would you like to be stranded with?

114. If you could go back in time and change one thing, what would it be?

115. If you could have lunch with any four people, living or dead, who would you choose?

116. What is the longest period of time you have gone without sleeping (and why)?

117. What is the tallest structure you’ve climbed to the top of?

118. What was the most recent movie you saw? What were your thoughts on it?

119. When you were younger, what did you want to be?

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

121. What superpowers would you have if you were a superhero?

122. If money were no object, what would you do all day?

123. If you could travel back in time, which year would you visit?

124. Write down two pet peeves. What one thing other than the basics, could you think of?

Deep questions to ask a guy you like

If you like someone then be cautious with your words. Because your words make a huge impact on him while communicating or making your relationship stronger.

Good and deep questions help you to pull him closer to you and know the positive and intelligent side that definitely attracts him towards you. So, here is the list of random questions to ask a guy you like. 

125. Is it easier for you to be an introvert or an extrovert?

126. Which parent do you have a stronger attachment to, and why?

127. What are your thoughts on tinder or internet dating?

128. What is your best friend that makes a huge impact on your life?

129. What are your thoughts on best friends who are of the other gender?

130. What gives you a sense of accomplishment?

131. What are your feelings regarding your password being shared with your partner?

132. Would you still love your partner if you found out they had a terminal illness?

133. What qualities in your parents do you admire?

134. What are some of your favorite musical compositions?

135. What was the most difficult time in your life?

136. What’s the most insane thing you’ve ever done, and would you do it again?

137. What would you wish for if a genie granted you three wishes right now?

138. What is one thing about yourself that you would like to change?

139. Would you ever forgive someone who cheated on you?

140. What do you consider to be a deal-breaker in a relationship?

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

142. When do you believe someone is ready to marry?

143. Is what you’re doing today something you’ve always wanted to do since you were a kid?

144. Have you ever experienced the loss of someone close to you?

145. Do you like to be left alone or have someone cheer you up when you’re in a foul mood?

146. What is the one thing about you that people consistently misunderstand?

147. What does a great vacation look like to you?

148. When was the last time you did something to break someone’s heart?

149. When you were younger, what did you want to be?

150. What type of parent do you imagine yourself to be?

151. Who is the one person you can talk to about anything?

152. Would you accept your significant other’s religion if he or she had one?

153. Do you think there is such a thing as a second chance?

154. What has been your worst mistake in life so far, and what have you learned from it?

155. What is your favorite destination to visit in the entire world?

156. What have you learned from your previous relationships?

157. What are the top five films that you enjoy watching?

158. What would you do if your parents didn’t approve of your boyfriend or girlfriend?

159. What is your all-time favorite book or movie, and why did it speak to you so deeply?

160. When was the last time you got a significant rush of adrenaline?

Deep questions to ask a guy about relationships

Are you interested in someone? Do you want to make your relationship stronger with your lover? Do you want to get closer to your lover?

Then, here is the desired set of questions you can ask a guy about relationships to know what he really thinks about relationships, love, personal life, and love life goals. Let’s take a look at the best questions to ask your loved one. 

161. How did you get along with your parents as a kid?

162. What has been the most enjoyable period of your life so far?

163. What were your feelings regarding school?

164. What was the most memorable trip you’ve ever taken?

165. Who was the first person you ever had a crush on?

166. What is the most significant chance you have squandered?

167. What was the length of your long-distance relationship?

168. What was the most daring decision you ever made as a kid?

169. What has been the most significant change in your life since you were a child?

170. What was the most bizarre lesson you learned from your prior relationship?

171. When you were a kid, what did you want to be when you grew up?

172. What were some of the customs in your family?

173. When you were younger, who did you look up to the most and why?

174. What’s the most ridiculous thing you’ve ever done for love for a cause?

175. What was your biggest fear as a child, and is it still fear for you today?

176. What’s the craziest thing you’ve ever done on a date?

177. What three words would you use to characterize yourself as a child?

178. How at ease do you feel discussing your past?

179. What was your worst fear as a kid, and is it still a concern for you now?

180. What’s the oddest dating activity you’ve ever done?

181. What three words would you use to describe yourself when you were a kid?

182. How comfortable are you talking about your past?

183. Have you ever doubted your ability to discover true love?

184. What was the strangest place you’ve ever made love?

185. What is your greatest apprehension about being in a relationship?

186. What would you do on a date if you only had $30?

187. What are your thoughts on dating someone who is still in contact with their ex?

188. Have you ever wished you hadn’t ended a relationship?

189. What is your most powerful non-physical turn-on?

190. Do you believe that true love necessitates a sacrifice?

Deep conversation questions to ask a guy

The conversation is the foundation of a happy and healthy relationship. And deep conversation adds extra spice to your love life. If you are someone who wants to build a deep and romantic relationship then a deep conversation is the right way.

Deep questions lead to deep conversation, so if you are someone who wants to have some extra love moments, then here is the list of questions. 

191. What words would you use to describe the ideal day?

192. Is there a decision in your personal life about which you feel guilty?

193. Which film has had the largest impact on you? What is your favorite fictional character?

194. When do you believe people should consider starting a family?

195. What three non-electronic or automatic items would you bring with you if you were stuck on a deserted island?

196. Who would you choose as the director of a film about your life, and why?

197. What skill do you have that you think others would find incredible?

198. Have you ever stayed up all night hoping to get a glimpse of the sunrise? What is the sweetest memory of date night?

199. How long has it been since you slept under the stars?

200. Would you rather be a world-famous pro-MMA fighter or a country’s president?

201. When was the last time you cried, and what was the cause?

202. Among your family members, who do you consider to be your closest confidant?

203. How would you spend a million dollars in three days if you were handed one today?

204. What two things would you need to survive a zombie apocalypse?

205. Which superhero was your favorite when you were a kid, and why?

206. What is your most amusing high school memory?

207. If you only had 10 days left to live, how would you spend the time you had left?

208. What’s the most recent item you’ve checked off your bucket list?

209. Do you have a favorite spot on the planet, and if so, where is it?

210. Which do you fear more: failure or success, and why?

211. What was the most memorable birthday you’ve ever had?

212. What was your first pet, and when did you get it?

213. What items or circumstances make you doubt yourself?

214. What do you consider to be your best achievement to date?

215. What would you do for those you care about?

216. What do you wish your family knew about you at this point in your life?

217. When was the last time you told someone you loved them?

218. Who would you choose to put your life on the line for if you had to?

219. Do you believe in fate or do you believe that events occur as a result of our choices?

220. If you had the chance, what period in history would you change?

221. How did it feel to grow up in your hometown?

222. Which of your senses would you give up if you had to?

223. What was your most humiliating job experience?

224. Do you prefer to work with your left or right hand, and would you be willing to switch?

225. In three words, how would those close to you characterize you?

226. What was the most humiliating thing you ever did for someone you care about?

227. Have you ever lost someone close, you cared deeply about?

228. Would you take an all-expenses-paid plastic surgery offer, and what would you change about your physical appearance if you did?

229. What’s the most essential thing you’ve learned from a family member?

230. Do you believe that people never change and only display their true colors when they do?

Best deep questions to ask a guy

Are you looking for the best deep questions to ask a guy? Then, here is the list of questions you can ask a guy, maybe your husband, lover, or crush.

Everyone wants the best things in life and here you also need the best deep questions. So, let’s get into it without a second thought. 

231. What do you hope people will remember about you after you’ve passed away?

232. What characteristics do you seek in a partner? What is the best piece of advice you have received so far?

233. What do you consider to be the ultimate comfort food?

234. What instrument would you play if you were in a band?

235. Who would you choose if you had the chance to exchange places with someone for a day?

236. Why or why not do you enjoy your given name?

237. Is there a purpose to your life, and if so, what is it?

238. Is there anyone you believe to be “the one who got away”?

239. What is it about other people’s actions that you find amusing?

240. Where would you choose to live if you could live anyplace in the world?

241. When things don’t go your way, how do you cope?

242. Is there a character in a movie or a cartoon who looks a lot like you? What do you mean by that?

243. Which of your habits do you think others might find strange?

244. In a relationship, what is your biggest regret so far?

245. Do you believe we create our own happy endings or do you believe they are determined by fate?

246. What was a long-held notion of yours that science recently disproved?

247. When you were ten years old, what was your most memorable adventure?

248. Is there any aspect of your personality that you believe you should work on? If that’s the case, which section and why?

249. What has been the most awkward circumstance you’ve recently encountered?

250. What would be the global greeting if there were one?

251. What kind of death do you believe you’ll have?

252. Are people, as a force, creative or destructive?

253. Why do you suppose that people believe in conspiracy theories?

254. Is it possible for the world to attain long-term peace?

255. Do you believe certain lives are more valuable than others?

256. Do you think there will ever be a day when computers outperform humans in terms of intelligence?

257. Is happiness simply a condition of mind, or do we have to take action to acquire it?

258. How would you rate the importance of these three factors: career, family, and love?

259. Would you die as a fulfilled or unsatisfied person if you died tonight?

260. What would you regret not doing if you died tonight?

261. At your funeral, what will people say about you?

262. Do you believe in an afterlife, and if so, why?

263. When was the last time you burst out laughing?

264. Would you consider relocating to a place where you have no relatives or friends?

265. What is a secret trait about yourself that you wish people were aware of?

266. Do you consider oneself to be religious or spiritual?

267. How would you define your life five years from now if all of your wants were granted today?

268. What is your most painful elementary school memory?

269. What is one personality feature or trait that you would like to change about yourself?

270. Is it easier for you to be an introvert or an extrovert?

Deep emotional questions to ask a guy

Everyone has an emotional part within themselves, but guys usually hide it. If you want to dig deeper into the emotional side of a guy then deep emotional questions are perfect to go.

Emotions also help to make the bond stronger and establish a deep and unbroken relationship for long life. So, let’s dig deeper into these types of questions to know a guy better. 

271. What has been the most daring thing you’ve done in your life?

272. In five words, how would your best friend describe you?

273. How would you sum up your life’s mission?

274. Have you ever had trouble sleeping? So, how do you spend your free time?

275. Tell me about your worst love regret, and why you wish you could go back in time.

276. Are you a materialist or a spiritualist?

277. If you were to choose only one religion on the earth, which would you choose and why?

278. Can you tell me about the most romantic and loving thing you’ve ever done for someone?

279. Give an example of anything that made your heart race and gave you a burst of adrenaline.

280. Tell me about a time when you were so ashamed in love that you thought you could just vanish.

281. Which would you choose if you had the option of becoming a zombie or dying?

282. What is the most important value you would teach your children if you had to choose only one? Is it more important to be honest, kind, or courageous?

283. Are you concerned about your health?

284. Describe the one defect in a spouse that you wouldn’t mind having.

285. Describe the one quality of a spouse that you can’t stand.

286. What is your most scary supernatural or paranormal fear?

287. What would you do if you were given a $5,000 free check right now?

288. Do you believe males are more rational, while women are more emotional?

289. Which of the unpleasant emotions of greed, rage, jealousy, and hate has the most impact on you?

290. What is your greatest strength among the good emotions of compassion, positivism, excitement, and initiative?

291. If you could be President of your country for an hour, what would you do differently?

292. Tell us about your favorite first kiss.

293. Has someone else’s suffering ever brought you joy? Be completely truthful.

294. Tell me about your greatest strength outside of work.

295. What animal would you choose as a pet if you could have any animal in the world, and why?

296. Which of the following would you select if you had the opportunity to explore the oceans, go to outer space, or visit 50 different countries?

297. What would you do if you had the option to pick and choose your own method of death?

298. Tell me a completely ridiculous joke that made you chuckle.

299. From physical chemistry, lifestyle compatibility, emotional compatibility, and intellectual compatibility choose two.

300. If you had to vote for one of history’s most famous dictators (Hitler, Mussolini, Saddam, or Stalin), who would you choose and why?

301. Show me a piece of music or a moment from a movie that made you cry.

302. What was your relationship with your parents like at home? Outside of the family, how does he or she behave differently? Which is the best relationship advice you have ever received?

303. Would you accept the chance to be immortal if it was offered to you?

304. What is the source of happiness? Define happiness for yourself.

305. Do you consider yourself completely free? If so, what’s the reasoning behind it? If not, what is preventing you from doing so?

306. Is it just chance or is there something to deja-vu?

307. Do you believe in parallel universes and other dimensions?

308. Would you choose to eliminate pain from your life if you had the opportunity? Why do you think that is?

309. Is it worthwhile to live a life dedicated entirely to pleasure (no suffering)?

310. What, if anything, do you believe happens after death?

Deep meaningful questions to ask a guy

Meaningful things make so much difference in life. If you and your partner are mature enough then why not to have some thoughtful and philosophical conversation.

You can ask these questions while sitting together or spending time together. Sometimes, these conversations also make your love life enjoyable. 

311. What book or film impacted you the most, and how?

312. In a romantic connection, what is your biggest turnoff?

313. Is your current career a reflection of what you said you wanted to be as a child?

314. Do you think the present is truly superior to the past?

315. Have you ever witnessed a serious case of poverty, and how would you describe it?

316. What are the realities or truths about which you are in denial?

317. Do you believe that the way you live your life makes a difference?

318. Why do you think you’d be willing to disclose your password with your romantic partner?

319. What are your thoughts on a cheating partner? What do you think about reproduced distributed?

320. What age do you believe people should marry?

321. Why do you think you’ll make a good parent?

322. What would you do if your parents didn’t like your boyfriend or girlfriend?

323. Do you think people of different sexes can be the best of friends?

324. Have you ever experienced the loss of someone close to you?

325. Who is the one person you can talk to and with whom you can discuss any topic?

326. When it comes to exes, do you believe in destroying bridges?

327. When you’re in a bad mood, would you rather have someone cheer you up or be left alone?

328. Do you keep a journal, and if so, how frequently do you update it?

329. Do you believe in giving cheating partners a second chance?

330. What is it about you that people constantly misunderstand?

331. What would you say is the best way to describe your ideal vacation?

332. What are the two most important lessons you’ve taken away from a previous relationship?

333. Do you believe that true love can be found in online dating?

334. What three wishes would you make if someone could fulfill them?

335. Are you willing to put your life on the line for someone, and if so, who?

336. What are the top five lessons you’ve had to learn the hard way?

337. Do you believe in science or magic?

338. How different would the world be if you hadn’t been born?

339. Are you willing to go above and beyond for something or someone?

340. Which comes out on top: reality or imagination?

341. When was the last time you told your parents, “I love you?”

342. Which is preferable: breaking hearts or being broken hearts?

343. Who would you choose to live with for a day if you could, and why?

344. Which of the following emotions best describes you, and why?

345. What do you believe will be the cause of humanity’s extinction?

346. Will you encourage your children and grandchildren to use social media?

347. What would you do with a billion dollars if you had it? How would you utilize it to help the less fortunate?

348. Which circumstance is preferable: being broke or being alone?

349. Would you rather be alone or surrounded by people you know when you die?

350. What has been your lowest point this year?

Interesting deep questions to ask a guy

Interesting and funny questions bring humor and fun. If you are someone who needs such great conversation topics then why not begin with asking interesting questions about life, love, healthy relationships, dreams, and random questions as well. 

Everyone loves to have humor in their life as it works as a stress buster then why not begin with these fun questions to ask a guy and it helps to bring you closer and intellectual for a lifetime. 

351. What has been the happiest moment of your life this year?

352. Who is hiding behind the mask you wear in public?

353. What would the title of your life be if it were a movie, and why?

354. On a scale of one to ten, how satisfied are you with your life?

355. When was the last time a film brought you to tears?

356. If you died today, what regrets would you have?

357. What is the most important goal you wish to accomplish in your life?

358. What do you want to be doing in ten years?

359. What is one aspect of growing older that you are looking forward to?

360. What is one destination you’d like to take someone else, and who would you take with you?

361. What would it be if you could know one thing about your future right now?

362. Is there anything about the future that makes you nervous?

363. Have you ever made an important prediction about your future that came true?

364. Would you rather have a young body or a young mind until the end of your life?

365. What do you believe will be the most amazing invention made in your lifetime?

366. Do you believe we have the ability to modify our destiny, or do you believe it has already been written?

367. What is one thing you wish to remember for your future self?

368. What is one memory you’d like to revisit when you’re older?

369. In the next five years, what are three things you aim to improve on?

370. What would be the first vacation you’d take once you’d retired?

371. What changes in your life would you be willing to undertake now if it meant retiring 10 years earlier?

372. What three new habits do you want to start this year?

373. What comes to mind when you hear the word “future”?

374. Who do you want to meet the most in the future?

375. In three words, describe what you want your future to be.

376. What would you call a book about yourself if you wrote one?

377. What reality show would you want to appear in if you had the chance?

378. What fantasy would you choose to make a reality if you had the chance?

379. What would you challenge the person asking you these questions to do right now if you had the chance?

380. What would you post on social media if you were to reveal your secret you’ve?

381. What would your favorite memory look like if it could be made into a physical object?

382. What would you pick if you had the option of going to heaven with your foes or hell with your friends?

383. Who would you choose to replace your siblings with if you had the option?

384. What one experience in your life stories would you change if you could?

385. What would you tell your younger self if you had the chance?

386. Where would you marry if you could get married anywhere in the world?

387. Would you want to know the date of your death if you could?

388. What portion of your body would you choose not to age if you had the option?

389. Who would you want to view your future if someone other than yourself could?

390. What would you tell if you could only make one joke for the rest of your life?

Deep questions to ask a guy before dating

Dating is a huge responsibility and commitment towards a person therefore if you want to date someone then it’s necessary to know every aspect of life, his failure, success, habits, life goals, and his thoughts on relationships. 

Therefore, to make your task easier we have curated the list of all questions we are looking to ask him before starting dating him. So, let’s have a look at deep questions to ask your boyfriend

391. Which would you choose if you could be a wizard or a genie?

392. Who would you prefer to grant the desires of if you had the power to do so?

393. What would you ask a crystal ball if you had one?

394. Do negative changes in a relationship occur after marriage? If so, what would you do to avoid these changes?

395. What is it that you can spend a little more money on in order to get better quality?

396. What do you consider to be a waste of money?

397. How do you feel about a wasted life?

398. What simple change in your life might you make that would have the most positive impact?

399. Who do you aspire to be like more?

400. What are your life’s most important objectives? What Steps Have You Taken To Achieve Them?

401. Which of the following is the biggest lie you’ve ever told?

402. What is the most difficult life lesson you have had to learn?

403. What are you ranting about or need to get off your chest?

404. What do you think you should be judging people for?

405. Would you rather face your fears or pretend they don’t exist?

406. Do you think of yourself as an extrovert or an introvert?

407. What do you do if you need to be alone?

408. Do you like beaches, mountains, forests, or fields in nature?

409. What name(s) would you give your children if you had the choice?

410. How would you adjust to prison life if you were falsely convicted of a crime?

411. What activity makes you feel calm and at peace with the world?

412. Would you give money to a homeless person who asks for it?

413. What would you do if you had $5 million?

414. Do you believe that a man should pay every time or that they should split the money as needed?

415. What qualities should a man possess when he is in a relationship?

416. Would you rather spend more time with your significant other, family, or friends? Why?

417. Who do you consider to be the most significant person in your life?

418. Who is the one person you can talk to about anything?

419. What are some examples of selfless acts that have improved your life?

420. What was a random compliment you received that stayed with you for a long term?

421. Have you ever done something crazy that makes you smile just thinking about it?

422. What has had the most significant influence on your political views?

423. What issue do the majority of people believe is black and white, but you believe has a lot of nuance?

424. Do you have any enemies? How do you deal with them?

425. Who have you completely lost faith in?

426. What did you enjoy doing once but will never do again?

427. Who are some people you’ve only met once but have made a lasting impression on?

Deep sexual questions to ask a guy

If you are lacking in your personal life and want to bring some romance and intimacy into your love life, then deep sexual questions are the best to ask a guy.

Here is the list of best deep sexual pickup line questions to arouse your partner and bring back the love and romance in your intimate moments. Let’s take a look into it. 

428. Do you like to cuddle or make out?

429. Can you tell me about the most memorable kiss you’ve ever had?

430. When we’re not together, do you think about me?

431. What are your thoughts on a girl initiating contact?

432. Do you remember ever having a dream about me?

433. How do you feel about premarital sex?

434. What role do you believe sex plays in a relationship?

435. Have you ever had sexual thoughts about me?

436. Do you believe you have a good understanding of what women desire?

437. If you couldn’t have me, who would be your dream girl?

438. Which portion of my body do you want to be tattooed?

439. What female outfits catch your interest the most?

440. How many other girls have you dated before me?

441. What physical characteristics in women catch your interest the most?

442. Do you think you’re more sexy or smart? What’s the first time you fall in love?

443. What was the first thing that drew your attention to me?

444. What makes you happy (if you know what I’m talking about)?

445. What would be the least appealing feature of mine if you had to pick one?

446. Are you more of a trousers or skirts kind of guy?

447. What is your most humiliating sex experience?

448. Who would you choose to have sex with if you could only have sex with one celebrity, and why?

449. Have you ever locked your eyes on my buttocks or chest?

450. When you’re in the mood, what do you wear to bed?

451. Have you had a one-night stand before?

452. What would you do to me if I were in your room right now?

453. Would you ever buy me lingerie as a present?

454. What area of a woman’s body do you appreciate the most?

455. What age were you when you had your first sex experience?

456. What do you consider to be ideal foreplay?

457. What’s the strangest thing you’ve ever wanted to do with a girl?

458. Which sex position is your favorite?

459. Have you ever been in a position where you were friends with benefits?

460. Would you ever sleep with the best friend of your ex?

461. Have you ever slept with someone and then wished you hadn’t?

462. What is the difference between sex and making love in your opinion?

463. What is one thing you want me to do in the bedroom that I haven’t done yet?

464. Is it acceptable to laugh in the bedroom, or must it be serious?

465. Kissing is said to burn calories, so do you want to join me in the gym?

466. Have you tried edible underwear before?

467. What should I be wearing right now, according to you?

Deep flirty questions to ask a guy

Do you want to ask some deep and flirty questions or a combination of both? Then, here you go.

Being flirty and romantic in front of your partner with the right set of questions makes your love life intimate and romantic as well. 

So, below is the list of deep flirty pick up lines questions that you can ask a guy when you want to make him closer and arouse towards you. 

468. What’s the dirtiest thought you’ve ever had about me?

469. Are you up for a game of dirty truth or dare?

470. What would you say or do if I sent you a photo of myself that was filthy?

471. Have you ever wished to rip off my clothes?

472. Do you appreciate it when I’m the first one to make a move in bed?

473. How can you relax me when I go home from work stressed?

474. Do you enjoy trying out different positions to see which one is your favorite?

475. What are your thoughts on love bites, and do you wish to try them?

476. Would you rather be seen as sexy or as intelligent?

477. Is there anything about you that surprises me?

478. What’s the one thing you’ve always wanted to ask me?

479. How many times have you been completely charmed by someone?

480. Before you go to sleep, what do you think about it?

481. So, what do you think we should do this weekend?

482. Do you find it satisfying to be in a long-term relationship?

483. If you answered yes, what do you enjoy the most about being in a relationship?

484. What would you be famous for if you could be famous for anything?

485. What’s a gift you’ve always wanted to get?

486. Do you prefer me to be naughty or nice?

487. Have I appeared in any of your dreams so far?

488. What is one of your favorite movies that I would be shocked to learn you enjoy?

489. What appeals to you the most and which is more important: intelligence or beauty?

490. Would you prefer to end a date with a kiss or a hint of mystery?

491. What have you always wanted to do with your partner but never have?

492. What movie title would you choose to describe your kissing technique if you had to choose just one?

493. What is one temptation that you can’t seem to avoid?

494. When someone likes you, how does she normally let you know?

495. Do you prefer a calm and lovely woman or a woman who is more assertive?

496. In three words, how would you define yourself?

497. Have you ever done something truly romantic?

498. Would you rather date someone intelligent or attractive?

499. How many people do you have a crush on at the moment?

500. On a first date, how far have you ever gone?

501. When you first saw me, what did you think?

502. Do you find it attractive when a woman flirts with you?

503. Apart from chatting with me, did you accomplish anything interesting today?

504. In a film about your life, who would you want to play your love interest?

505. What would it be like if we went on a date?

506. When you first meet someone, what is the first thing you notice about them?

507. Do you believe that men should always initiate contact?

508. What do you think of our first date?

509. Do you prefer text communication or face-to-face communication?

510. Who was your celebrity crush when you were a child?

The wrapping up

We hope this helps you with some fresh good ideas for deep questions to ask a guy. Asking deep questions can be a great way to learn more about others, strengthen your closeness with each other, and have more engaging talks.

Hopefully, these lists of deep questions gave you a perfect pace to start. 

Don’t leave any chance to get into a deep conversation with your partner. Because that can lead your relationship to the next level and will make both of you more engaged and interested in each other.

It’s necessary to bond with him in all aspects of life and conversation helps in this case. This also helps in making him closer to you if you are feeling he is getting distant and distracted from you.

So, what are you waiting for? Just grab him and get into a deep conversation.