351 Fun Questions That Will Bring You Closer Than Ever to Your Boyfriend

Looking to spice up your relationship and get to know your boyfriend on a deeper level? 

We have you covered with 351 fun, provocative questions guaranteed to bring you closer. 

From playful questions you can ask while texting to more intimate questions that reveal his innermost thoughts, these conversation starters will uncover new sides of his personality. 

Whether you want to make him blush, learn more about his past, or spark funny debates, this extensive list of questions for your boyfriend covers it all – from lighthearted to serious to sexy.

351 Fun Questions to Ask Your Boyfriend 

1. What's your favorite memory of us together so far?

2. Who's your celebrity crush, and why?  

3. What's something you're excited about right now?

4. If you could live anywhere in the world, where would it be?

5. What's one thing on your bucket list?

6. What's your favorite sport to watch and play?

7. What hobby would you get into if time and money weren't an issue? 

8. What's the most spontaneous thing you've ever done?

9. Do you believe in love at first sight, or should I walk by again?

10. What's your favorite season and why?

11. What mythical creature do you wish actually existed?

12. What's your biggest fear?  

13. What's your favorite family tradition?

14. What's your dream car?

15. Who's someone you really admire?

16. What's the most thoughtful gift you've ever received?

17. What's one thing you want to accomplish this year?

women talking in car Fun Questions to Ask Your Boyfriend 

18. What's the most amazing place you've ever traveled to?

19. What's your favorite late-night snack?

20. What songs have you completely memorized?

21. What movies make you cry like a baby every time?

22. What's your biggest pet peeve?

23. What's your dream job besides your current one? 

24. What fictional place would you most like to go to?

25. Do you believe in astrology? Why or why not?

26. What's your Myers-Briggs personality type

27. What's your worst habit?

28. What's your greatest strength?

29. What's the most rebellious thing you did as a teenager?

30. Who was your childhood celebrity crush?

31. What food do you crave most often?

32. What's your favorite guilty pleasure TV show?

33. What popular trends have you never really understood?

34. What children's movie could you watch over and over?

35. What actor or musician would you most want to meet and why?

36. What songs are at the top of your shower playlist?

37. What's one skill you'd love to learn? 

38. What's the ideal dream date, in your opinion?

39. What quirks do you find cute in a partner?

40. What's something you believe that others find odd?  

41. What's your most embarrassing childhood memory?

42. What's something you can talk about for hours?

43. What's the most useless talent you have?

44. What's your favorite way to waste time?

45. What random fact are you most proud to know?  

46. What food have you never eaten but would really like to try?

47. What hobby or activity has brought you the most joy?

48. What websites or apps could you browse for hours?

49. What's the most amazing natural wonder you've seen in person?

50. What celebrity death impacted you the most?

51. What scientific discovery or advancement excites you most?

52. What songs do you only sing in the shower?

53. What's the most ridiculous business idea you've come up with?

54. What outdoor activities do you love most?

55. What smartphone app could you not live without?

56. What animated character reminds you most of yourself?

57. If you were a wrestler, what would your entrance theme song be?

58. What's been your most life-changing experience so far?

59. What pointless skills are you proud to have?

60. How often do you people watch, and what's the best story you've imagined?

61. What world records do you think you could break?

62. What's the most creative way you've cheated at something?

63. What outdoor or public space do you wish existed in our city?  

64. What YouTube channels are your guilty pleasures?

65. What songs do you have to sing along loudly to every time?

66. What “old person” things do you do already?

67. What TV show do you wish never got canceled?

68. What's your most prized nerdy possession?

69. What arguments or debates will you never back down from?

70. What smartphone feature seems like magic to you, even now?

71. What's the spiciest food you've ever tried?

72. What supposedly “grown-up” habit did you pick up early?

73. What topic could you talk to a stranger about for 2+ hours?

74. What fantasy pet would you want if you could have any animal?

75. What actor would be terrible casting to play you in a movie?

76. What celebrity gossip do you pretend not to care about but secretly love?

77. What game or trivia subject are you unbeatable at?

78. What social media trend always gives you secondhand embarrassment?

79. What snack are you obsessed with lately?

80. What hobby seems boring but is shockingly fun?

81. What life skills are rarely taught but extremely useful?

82. What sport could you play professionally if you practiced enough?  

83. What inanimate object would be the most annoying if it played loud, upbeat music while being used?

84. What movie genres do you find overrated or not worth watching?

85. What actor's career took an unexpected turn?

86. What foods and drinks bring you the most nostalgia?  

87. What problem or situation did you think was awful at first but later was grateful for?

88. What popular movie or book genre have you never enjoyed?

89. What comedian don't you find funny?

90. What talents and skills would you love to learn someday?

91. What quirky little things does your pet do?

92. What questions keep you up at night?

93. What actor or public figure seems like they'd be impossible to hang out with?

94. What amazing sights do you still want to see in person someday?  

95. What collectibles do you display proudly?

96. What candies and sweets do you still enjoy eating regularly?

97. What board game rules did your friend group make up variations of?

98. What hobby would you be embarrassed for your friends to find out about?  

99. What personality traits do you appreciate most in other people?

100. What future technology are you skeptical or pessimistic about?

101. What trend needs to make a comeback?

woman smiling looking at phone Fun Questions to Ask Your Boyfriend 

Fun Questions to Ask Your Boyfriend While Texting 

102. What emoji best describes your mood right now?

103. What are your plans for this weekend? Any fun ideas?

104. Just saw (insert something relevant and funny). Made me think of you! What's the last thing that randomly reminded you of me today?

105. What gif or meme never fails to make you laugh? Send it to me! 😂

106. If you were a brand, what would your slogan be?

107. What's something good that happened today, even if it's small?

108. If you could only text using gifs and emojis for the day, how would that go?

109. Where's the most breathtaking place near you that you'd take me on a date? 

110. What's your favorite dessert? Let's grab it this weekend!

111. What are three unique things on your bucket list?

112. What's the craziest viral video you've seen recently? You have to show it to me later!

113. If you could have an all-expenses paid trip anywhere in the world, where would you go?

114. What's your favorite song to belt out in the car or shower?

115. What's the best purchase you've made recently?

116. Thinking of planning a fun weekend trip for us soon! Any places you'd want to go together?

117. What's your favorite way to relax after a stressful day?

118. Just saw this dog/cat/etc. that looked just like (your pet's name)! Do you see the resemblance?

119. Don't make any other plans Saturday night. I'm planning an awesome date! Any clues on what we're doing?

120. What are three fun facts about yourself I probably don't know yet?

121. Who's someone famous you get compared to a lot?

122. Summarize your dream house in emojis!

123. What's the best or worst dating advice someone's given you?

124. What's your go-to pumped-up playlist for the gym? 

125. What's something you can talk about for hours that you think I'd find interesting?

126. Where's the most jaw-dropping place you've traveled to? I need to see the pics later!

127. What food have you never liked, no matter how many times you've tried it?

128. What’s your favorite moment of the past week? Send me a pic to capture the memory!

129. What's your favorite spot in our city that not many people know about? Our next date spot, perhaps?

130. What is your perfect day using only emojis?

131. What quirks do you notice about me that you find cute or endearing?

132. What hobby or activity have you always wanted to try but haven't yet? We should try it together!

133. What trend or meme are you tired of already?

134. What random fact did you recently learn that blew your mind?

135. What food have you been craving lately? We're getting it this weekend!

136. What's your favorite thing to do together as a couple? More date ideas for the future?

137. What’s the most ridiculous dream you can remember? Summarize it with emojis!

138. What funny or weird things does your family do that outsiders would find hilarious?

139. Looking for new music! What's a song you've had on repeat lately?

140. What food do you love even though it's messy and kind of inconvenient to eat? Worth it! 

141. What movie makes you cry happy or sad tears every time without fail?

142. What childhood activity do you wish you could still do now as an adult for fun?

143. What's your strangest habit that I probably don't know about yet?

144. What hobby seems boring but is actually really fun once you try it?

145. What TV show or movie do you secretly enjoy that you're embarrassed to admit you love?

146. What is a funny gif that sums up how your week is going so far?

147. What three things always brighten your mood when you're feeling down?

148. What phone app do you wish someone would develop for you?

149. What food smells so good but then disappoints once you taste it?

150. What topic could you spend hours passionately defending to someone?

151. What is your dream vacation? Summarize it in emojis! 

Fun Sexual Questions to Ask Your Boyfriend 

152. What’s your favorite part of sex?

153. What’s the sexiest outfit I could wear for you?

154. What’s one sexual fantasy you have about us?

155. How often do you think about sex each day?

156. Where's your favorite spot to be kissed gently?

157. What's the sexiest photo you’ve ever taken? Maybe you could show me later 😉

158. How do you feel about experimenting with new positions? Any you've been wanting to try?

159. What sensual touch really turns you on?

160. What's your favorite way for me to initiate intimacy? 

161. Have you ever been in a threesome? If not, would you consider it?

162. What sex toys have you used before? Any you loved?

163. Do you like being more dominant or submissive in bed?  

164. Is there any kink or fantasy you want to explore but haven't told me?

165. Where's the most public place you've ever had sex?

166. Have you ever gotten a lap dance? How did you feel about it?

167. What's the steamiest dream you've had about me? Tell me all the details!

168. What's the sexiest song you've heard? We should play it next time!

169. What's your favorite sexual position?

170. Have you ever had sex outside? Would you do it with me?

171. What's the hottest sext or message you've ever gotten?

172. Do you prefer giving or receiving massages? With or without oil?

173. Have you ever been tied up or handcuffed? Did you enjoy it?

174. What's one thing I could try in bed that would drive you wild?

175. Have you ever received sexy photos from someone else? Did you save them?  

176. What's one sexual activity you've done and enjoyed that might surprise me?

177. When, where, and how did you lose your virginity? How was your first time?

178. Have you ever gotten a private dance or hired an escort or sex worker? How was it?

179. Do you like dirty talk? What gets you going the most?

180. How and where do you prefer to be touched?

181. Do you own any sexy outfits you'd wear for me if I asked?

182. What's your number one sexual fantasy? Let's make it come true!

183. What's the most intimate sexual experience you've had with someone? 

184. What's your favorite part of the female body?

185. Do you own any sex toys we could use together? If not, want to shop for some?

186. Is there anything you consider absolutely off-limits sexually? 

187. What scene in a movie or book have you found seriously hot?

188. Where would your dream sex location be?

189. Have you ever had a one-night stand? Tell me about it!

190. Do you prefer rough or sensual intimacy? 

191. What's the most risque thing you've ever done sexually?

192. Have you ever gotten frisky in a changing room? How daring!

193. What's the most surprising place you've had sex so far?

194. Have you ever filmed yourself having sex? Would you want to make a tape with me?

195. What's one sexual act you badly want to scratch off your bucket list?

196. Have you ever had a friends-with-benefits situation? How did it start?

197. Is there any risky place you'd be open to getting it on if I initiated it?

198. What's your hottest secret fantasy involving me? Don't be shy!

199. What's the craziest sexual proposition you've ever gotten from someone?

200. Describe your ideal romantic evening leading up to sex.

201. Is there anything I do in bed you absolutely love? Tell me so I keep doing it! 

Random Fun Questions to Ask Your Boyfriend 

202. What random food combo do you absolutely love?

203. What's the most ridiculous thing you and your siblings argued about as kids?

204. What mythical creature do you wish existed and why? 

205. What's the weirdest advice anyone has given you that actually turned out to be true?

206. What food do you crave most late at night?

207. What's the weirdest thing that's happened on public transportation while you were there?

208. What quirky little tasks always give you a strange sense of satisfaction?

209. What skill can you learn in 30 minutes that will be useless but impressively fun at parties?

210. What funny curses from books or movies do you want to start using in real life?

211. What food or drink seems to be loved by everyone except you?

212. What's the most embarrassing object you still own from your childhood?

213. What activity do you find weirdly and unexpectedly zen?

214. What part of your morning or nightly routine do you always secretly look forward to? 

215. What random word or phrase always makes you laugh for no clear reason?

216. What irrational fear did you have for an embarrassing number of years?

217. What celebrity interaction or rumor completely changed your opinion about someone?

218. What did you only recently realize you've been doing the “wrong” way your whole life?

219. What's the most ridiculous thing you've seen someone get upset about?

220. What safety rule do you break all the time without any problems (yet)?

221. What product way exceeded your expectations after years of doubting it?

222. What common assumptions about you are hilariously wrong?

223. What belief did you do a total 180 flip on as you got older?

224. What trend did you mock at first but are now 100% obsessed with?  

225. What TV show did you think you'd hate but ended up loving?

226. What slang makes you cringe or annoys you every time someone says it? 

227. What product or brand has forever earned your loyalty?

228. What hobby seems super weird and bizarre…until you try it yourself?

229. What country has the most amusing or weird slang words, in your opinion?

230. What food have you never been able to get yourself to eat, no matter how many times you've tried it?

231. What rule or policy truly never made sense to you?

232. What body part or function seems hilariously useless?

233. What trend desperately needs to make a comeback soon?

234. What movie universe would be the worst to actually live inside?

235. What food do you crave when you're emotional (happy, sad, stressed, etc.)?

236. What product solved such a trivial issue that it seems hilarious in retrospect? 

237. What mind-blowing food mashup combo did you invent and love to your own surprise?

238. What hobby seems boring but is shockingly cathartic and fun?

239. What city has the most hilarious or awful local commercials?

240. What part of wedding traditions feels seriously outdated to you?

241. What food mashup combo did you try, convinced it would be awful, but you ended up loving it?

242. What crossover TV show episode would make the most ridiculous plot imaginable?

243. What extremely specific insecurity did you have as a teenager that seems laughable now as an adult?

244. What animal seems cute but is actually incredibly dangerous that no one appreciates?  

245. What comedian or style of comedy did you use to dislike but now find hilarious?

246. What trend are you 100% convinced is never coming back, despite how much you love it?

247. What personality trait did you only realize you had when others pointed it out?

248. What city has the most absurd unwritten social rules that outsiders always unknowingly break?

249. What food have you tried and would rate 0 stars out of 5?

250. What body part seems hilariously counterproductive for humans compared to other animals?

251. What product discontinued years ago do you still miss regularly? 

Fun Questions to Ask Your Boyfriend When You're Bored 

252. Who's the funniest person you've ever met, and why?

253. What's the most childish thing you still do sometimes?

254. What food do you crave when it's cold and rainy out?

255. What outdoor activities do you find overrated or not worth the effort?

256. What TV show or movie trope are you tired of seeing?

257. What trend are you tired of hearing about or seeing everywhere?

258. What popular hobby seems super boring and lame to you?

259. What's the funniest comedy special you've seen and can watch over and over?

260. What animal or insect do you have an irrational fear of?

261. What food do you love despite its horrible reputation?

262. What city doesn't live up to all the hype, in your opinion?

263. What actor plays the same character in almost every movie and TV role?

264. What workout or exercise trend is totally overrated in your view?

265. What fashion trend makes you cringe or shake your head every time you see it?

266. What politician can you do the best imitation of?

267. What dance moves or routines do you wish you could master?

268. What game show would you most want to compete on and win?

269. What actors or public figures would make the most awkward couple imaginable?

270. What food have you never eaten but want someone to describe the taste to you? 

271. What viral video makes you laugh uncontrollably every time you watch it?

272. What ice cream topping combination sounds disgusting but is actually delicious?

273. What otherwise boring activity is endlessly fun if you make it a competition?

274. What's the most annoying stereotype people make about where you're from?

275. What outdoor activity seems awful but is actually really fun once you try it?

276. What song can you listen to on repeat without ever getting sick of it?

277. What's the most delicious food combination you've come up with while bored and in desperate need of a snack?

278. What food do most people love, but you just don't see the appeal?

279. What comedian or actor would make the funniest president?

280. What movie do you love so much that you can practically quote the entire script?

281. What trend desperately needs to disappear in 2023?

282. What food have you forced yourself to acquire a taste for but just can't start liking?

283. What popular hobby or activity seems fun on the surface but is overrated in your opinion? 

284. What celebrity or public figure can you do a flawless impersonation of?

285. What game challenges from your childhood seem ridiculous and even dangerous now as an adult?

286. What food have you never eaten because the smell alone puts you off every time?

287. What song lyric or line would make a great ironic tramp stamp tattoo?

288. What movie were you way too young to watch when you first saw it?

289. What social media platform or app would be way more fun if you could stay anonymous on it?

290. What film genre needs to permanently retire? 

291. What fashion trend from long ago do you hope never comes back in style?

292. What comedian is beloved by everyone except you?

293. What city near where you live is painfully overrated?

294. What movie universe would be terrifying to actually exist in?

295. What actor plays practically the same exact character in every movie role?

296. What popular self-care advice actually stresses you out more than relaxes you?

297. What trend are you pretending is already over even though you know it's not?

298. What TV show should have stopped seasons ago?

299. What fashion trend makes you cringe when you see it?

300. What actor plays the same character in everything, and it's gotten out of hand?

301. What food do you refuse to try, no matter how much people rave about it?

Fun Questions to Ask Your Boyfriend About You 

302. What do you find most attractive about me physically?

303. What do you think my greatest strength is?  

304. What's your favorite thing to do together as a couple?

305. What's your favorite quality about me?

306. What's one thing you were surprised to learn about me?

307. What do you think I'm most passionate about?

308. What's one quirk of mine that you find adorable?

309. What's your favorite outfit of mine?  

310. What's one way I've encouraged or inspired you?

311. What's your favorite memory of me so far?

312. How would you describe me in 3 words?

313. What's the most thoughtful thing I've done for you?

314. What's your favorite gift you've gotten from me? Why did you love it?

315. What tradition or experience did I introduce you to that you now love?

316. What's something you thought you knew about me that I proved wrong?

317. What's your favorite way I show you affection?

318. What's one way I always know how to make you feel better?

319. What's something I do that you find funny or charming?

320. What life goals and ambitions of mine do you most admire?

321. What's one of my hobbies you find most intriguing?

322. What do you think is my greatest accomplishment so far?

323. What's your favorite inside joke we share?

324. What's something I've taught you or helped you understand better?

325. What's your favorite nickname or pet name you have for me?

326. What's something I say all the time that always makes you smile?

327. What's your favorite thing to do together at home?

328. What's your favorite romantic gesture from me?

329. What's a moment when you realized you were falling for me? Tell me about it.

330. What's your favorite place we've traveled to together?

331. What's your favorite meal I've ever cooked for you?

332. What relationship advice have I given you that you found really wise?

333. What's one way I always know how to cheer you up when you're in a bad mood? 

334. What's one of my habits or quirks you find really endearing?

335. What's your absolute favorite quality about me as a girlfriend?

336. What's one way you think I positively influence you to be a better person?

337. What's something I'm talented at that still impresses you?

338. What's your favorite romantic memory of the two of us so far?

339. What's something I'm knowledgeable about or skilled at that you find attractive?

340. What silly or useless skill of mine always makes you laugh?

341. How would you describe my best physical feature?

342. What's the most thoughtful thing I've done for you since we started dating?

343. What's one of my quirks that you've grown to love?

344. What's the most meaningful gift I've given you? What did you love about it?

345. What random act of kindness from me has stuck with you?

346. What habit or quality of mine initially surprised you but now you adore? 

347. What's something I do that you find hilarious?

348. What do I do that always brightens your day?

349. What's one of my hidden talents that not many people know about?

350. What's your absolute favorite memory of me since we started dating?

351. What song or movie reminds you most of me? Why?

What Are the Benefits of Asking These Fun Questions to Ask Your Boyfriend?

Asking these fun, thoughtful questions is one of the best ways to strengthen your bond and get to know your boyfriend on a deeper level. With this extensive list of 351 questions, you'll spark meaningful conversations, create lasting memories, and watch your relationship flourish. 

Strengthen Intimacy and Trust

Asking lighthearted questions about his past, thoughts, and opinions fosters emotional intimacy. The more you know about his inner world, the closer you'll feel, and the more he'll trust you with his vulnerability. 

Discover New Things About Him

You probably know his basic biographical details, but these creative questions will unveil surprising facts, childhood memories, secret passions, and adult dreams you never knew before.

Have Endless Conversation Starters 

Whether you're on an awkward first date or a married couple of 50 years, fun questions get the words flowing. Skip the boring small talk and delve into his world. From funny hypotheticals to thought-provoking reflections, these questions deliver engaging dialogue.

Create Inside Jokes and Shared Memories

The questions about you specifically build intimate rapport as you laugh about favorite memories and create new private jokes. Reminiscing about meaningful moments deepens your emotional bond.

Flirt, Tease, and Grow Closer

The flirty and risque questions bring out your playful sides and help you feel more comfortable being vulnerable. They open the door to new experiences together and encourage open communication about your sex life.

Spark His Interest

Fun, original questions show you're interested in who he truly is under the surface. They grab his attention, make him feel special, and keep the conversation exciting so your bond continues growing stronger.

How to Use These Questions to Ask Your Boyfriend for Fun

With over 350 questions to choose from, you can connect with your boyfriend in countless ways. Here are some tips to get the most bonding, laughter, and intimacy out of these questions:

  • Ask lighthearted questions during long drives or over a home-cooked meal together to learn new things about each other. The thoughtful questions, in particular foster emotional intimacy.
  • Keep things flirty and have fun teasing him with romantic or sexual questions when you want to spice things up. Send a provocative question over text and build anticipation for your next date night.
  • Break the ice on awkward first dates by asking funny hypotheticals or silly questions to get the conversation flowing comfortably.
  • When you're bored at home together, try the random questions or ones about each other to laugh, get creative, and make new memories.
  • Text him a fun question while he's at work to brighten his day and remind him you're thinking about him. Emoji-filled questions work great over text!
  • Ask light questions to fill time on long road trips or as daily “check-ins” to strengthen your bond. This regular intimacy will make you closer.
  • During a romantic walk or as you're falling asleep together, use thought-provoking fun questions to provide deeper insight and closeness.
  • Inject humor into dull moments by asking funny “this or that” style questions or hypotheticals that reveal his quirky side.

Final Thoughts

At every stage of your relationship, these 351 questions will uncover new layers of his personality, create meaningful conversations, and strengthen your intimate bond. Keep things light and playful or go deeper – either way, you'll get quality time, emotional intimacy, lots of laughs, and endless memories with the boyfriend you love.

Discover fun questions to ask your boyfriend. Spark conversations and deepen your connection through engaging dialogue.