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350+ Fun Questions to Ask your Boyfriend – A Master List

350+ Fun Questions to Ask your Boyfriend – A Master List

Updated on May 17, 2022 | Published on September 30, 2021
Reviewed by Julianne Cantarella, MSW, LSW, Certified Relationship Coach
350+ Fun Questions to Ask your Boyfriend - A Master List

If you are looking to have some meaningful conversation with your boyfriend and to draw his whole attention to your conversation rather than receiving one-liner boring responses then get ready for an entertaining list of fun questions to ask your boyfriend. 

Taking the time to communicate helps bridge the gap, get to know each other more closely, and create some memorable memories to be cherished for a lifetime. 

If you want to make your conversation fun and memorable, here is the list of questions that can lighten up the atmosphere and draw your boyfriend’s attention. Here we go! 

350+ Fun Questions to Ask your Boyfriend - A Master List
350+ Fun Questions to Ask your Boyfriend – A Master List

Starter fun Questions to ask your boyfriend  

Asking your boyfriend questions using these starter questions will help you establish the right mood and put you in the right frame of mind for the conversation. To keep the conversation going, choose ones that fit your style and use them according to your preferences. 

1.  If you could have the perfect day, what would it be like?

2. Do you have any lessons you learned too late?

3.  Is there anything you are too hard on yourself about?

4.  Do you ever feel completely worn down?

5. Have you read any books recently?

6. Do you have any habits that annoy other people?

7.  Is there anything that makes you nervous?

8.  Do you ever become angry for reasons you don’t understand?

9. How about those movies that made you cry so hard you may never watch them again?

10. Which two lessons have you learned from your previous relationships?

11.  Which aspect of your parents’ raising you was the most valuable?

12.  What is the best thing about aging for you?

13. What is the most obvious sign of weakness in a person?

14. Did you ever try really hard to enjoy something but just couldn’t?

15. Is there anything that differentiates you from other people?

16. Where would you go if you dropped everything and went on a road trip? Do you have a bucket list? 

17.  How did you behave at your manliest and least manly moments?

18. What do you think about pets and animals?

19. What do most people underestimate or overestimate about you?

20.  If you were forced to live your life over again, what would you do differently?

Fun questions to ask your boyfriend

You can instantly change a mood and balance a conversation with fun questions. You may use them on any occasion, even in the middle of deep conversation, for stupid unnecessarily funny comments to lighten the mood, or to ask casually. There are all kinds of questions to suit your mood and needs. 

21. If you had to make up a conspiracy theory on the fly, what would it be?

22.  Do you have any ideas about potential slogans for jobs/careers?

23. How do different hairstyles suit different personalities?

24. Is there anything that makes your brain scramble just by thinking about it?

25. How would each color taste if it had a taste?

26. Do you have any feelings of hatred toward any fictional villains?

27. Is there something you can buy/do for less than 20 dollars that will relieve stress?

28. What is the thing you often forget when entering a room?

29. If you had just your hands and feet, what would be the strongest animal you could beat?

30. What would you do if you got to spend eternity with a group of people who died the same way as you?

31. What would it be like to visit an amusement park filled with all your worst fears? Which rides would you find there?

32. Have you ever wanted to learn how something was made or how it works but never did?

33. Which names have you avoided because you knew someone terrible who shared the same name?

34. What kind of machine would you prefer to control if you had a remote control that controlled any kind of machine?

35. How are you doing something even though it’s incredibly inefficient or silly because that’s the way you’ve always done it?

36. Have scientists discovered anything cool in the ocean?

37. Do you remember a funny/strange thing a drunk friend confessed to you?

38. What would you put on your city’s main street if someone let you put whatever you wanted there?

39. Is there anything that you think would be fun to top ice cream with that is not traditional?

40. When it comes to ice cream cones, how much ice cream should you use?

41. Which animals would be uniquely qualified for certain jobs if they were as intelligent as humans?

42. If you had to choose a winner in a fight between A and B, who would it be?

43. What if you were able to say the same thing to everyone in your country at the same time? Which sentence would cause the most people to hate you instantly?

44. What song would you choose to dance to if you had to compete in a dance competition?

45. Is there anything that would prevent you from accepting immortality if you were given it with one condition?

46. Your dream name would be, if you had the chance to change your first name, what would you choose?

47. Is there any reason that we dream?

48. How long would you be willing to switch genders for if you could?

49. Do you have an example of a product you disagree with that has not been improved?

50. Describe the type of scented candle you would make if you could make it with any scent.

Fun questions to ask your boyfriend while texting

Texting is an interesting and fun way to communicate. Even if you are physically far from each other, it keeps you connected and close. You’re going to love the super fun and exciting questions that will spice up your conversation.

51. If you could change anything about your childhood, what would it be? How about what you would never change?

52. Has anyone ever gotten pregnant because of you? How did you deal with it?

53. How would you change one aspect of yourself if you could?

54. Do you remember the last time you cheated on anyone? Were you ever cheated on?

55. Do you have any regrets?

56. Is there anyone you’re jealous of?

57. How would you respond to people who have a misconception about you?

58. What is it like to spend the night in jail?

59. Would you consider going to therapy?

60. Do you have any experience breaking up with friends?

61. Do you still keep in touch with your ex-partner?

62. Which bad habit would be the most difficult for you to break?

63. What is the most embarrassing thing you’ve ever done to your partner?

64. How many times has your heart been broken?

65.  Have you ever received a strange text or call with a wrong number

66. Your go-to lame joke?

67. Have you recently Googled anything?

Fun deep questions to ask your boyfriend

Deep questions transport you to your own world. The memory and emotions connected to them transport you back to good times and let you imagine the best-case scenarios. Your conversation will be more intimate and special by answering these deep questions with a pinch of humor. 

68. Have you ever thought about having children?

69. The longest relationship you had lasted how long? What caused it to end?

70. What has your relationship or marriage experience been like? How do you feel about getting married?

71. What is your experience of living with your partner?

72. Do you consider religion and spirituality important?

73. What are your thoughts on gay rights?

74. What is your opinion about money being able to buy happiness?

75. Is there a job that would make you happy?

76. What is one thing you wish to achieve in your life?

77. How do you feel about your greatest achievement?

78. Who or what are you afraid of? When did you last vote?

79. How do you feel when you are alone or around other people? Are you an introvert or an extrovert?

80. Are you a grudge holder?

81. Has addiction ever been a problem for you?

82. Did you ever experience physical or emotional abuse in a relationship?

83. When a relationship ends due to cheating, can it be repaired?

84. Which event from the past would you most like to see recorded?

85.  How would countries settle their differences if wars were abolished?

Fun game questions to ask your boyfriend

Has your boyfriend ever played games with you? How often do you do it? By asking these questions, you will be able to start a casual conversation about various topics, which will allow you to learn more about each other and have fun together. 

86. Which is the most embarrassing event you have ever experienced?

87. What is the strangest thing you’ve ever purchased?

88. Have you ever visited a palm reader?

89. How would you choose among a personal trainer, a chef, or a housekeeper?

90. Would you be a woman if you could spend one day as one?

91. Which movie have you seen so many times you can’t even keep count?

92. Could you be portrayed by an actor if a movie were made about your life? Is there an actress who would play your love interest?

93. When you were in high school, what were you like?

94. How does your relationship with a fictional character compare to your relationship with real life?

95. Do you prefer to be hot or cold?

96. If you go to sleep, do you need to leave the closet door open or closed?

97. When you stay at hotels, do you ever take bottles of shampoo or conditioner with you?

98. How do you sleep? Do you keep your legs tucked in or do you place one leg inside and the other outside?

99. Do you remember stealing anything before?

100. If you were attacked by a grizzly bear or hornet nest, which would you prefer?

101. When you walk, do you ever count your steps?

102. If you don’t have music playing, would you dance anyway?

103. What do you think of cartoons?

104. What would you do with a treasure buried underground?

105. How would you describe your spirit animal?

106. Is there something you want to do together that we haven’t done before?

107. Do you have a new nickname/pet name you would like to use for me?

108. Did you like any particular trait of mine?

109. What was your first impression when we kissed?

110. How would you like to be hugged or kissed?

111. How would you feel if our relationship ended? What is the one thing you’d miss the most about it?

112. Are there any aspects of our relationship that you feel need improvement?

113. In our relationship, have I made you feel vulnerable?

114. Would you mind telling me one secret you haven’t shared with me?

Fun relationship questions to ask your boyfriend

The fun relationship questions are perfect for you when you want to discuss different aspects of your relationship with your boyfriend while having fun.  

115. How important is a physical connection or an emotional one in a relationship?

116. Which relationship among the ones you have with friends and family do you value most?

117. What are the most important qualities a partner should possess?

118. How would you describe my first impression?

119. Which of these things would be the sexiest to wear on a date?

120. What would be the perfect date for you?

121. Has there ever been an idea you’ve always wanted to do for your couple’s Halloween costume?

122. If you and your partner were to move, would you do it?

123. Are you keeping mementos of previous relationships? Are they notes, photos, and gifts?

124. What has been the most absurd thing you have ever done to impress someone?

125. When was the last time you kissed someone under mistletoe?

126. What are your thoughts on love at first sight?

127. What do you find most enjoyable about dating?

128. What do you think about fate?

129. Which of your relationships has required you to make the biggest sacrifice?

130. Is there a love song that you particularly enjoy?

131. How satisfied are you with the level of intimacy we share?

132. Would you mind sharing how we can support each other better?

133. What positive impact are we having on each other?

134. What are we doing to each other if we enable each other’s bad habits?

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

136. When we were together, what do you remember most fondly?

137. What would be the best trip to take together?

138. Do you want to learn a new hobby or skill together?

Fun sex questions to ask your boyfriend

There is no better way to ask your boyfriend some sexy questions than mixing up with some naughtiness and fun questions that will turn up the heat between you two. Here is the list of questions to ask your boyfriend

139. What is your most cherished sexual fantasy? How likely is it that you would do it in real life?

140. Is there another place outside the bedroom where you like to have sex?

141. Did you ever get walked in on while having sex? Are you ever caught by another person?

142. When you were in bed, what was the most ridiculous thing you ever did? What did you do?

143. Would you consider yourself a porn fan? Do you enjoy certain types of porn?

144. In which position do you feel most comfortable? In which position do you feel least comfortable?

145. Can you tell us about your most sensitive erogenous spots that you don’t always recognize? Those would include your lips, ears, neck, etc.

146. Which part of sex is your favorite? A form of foreplay or teasing, penetration, oral sex, or pillow talk.

147. In a role-playing scenario, what would you have me dress up as?

148. Did you attend a dominatrix in the past, or would you attend one in the future?

149. Would you like to try any sex toys?

150. Is there any word or phrase that turns you on?

151. What is the strangest thing that you find appealing?

Fun interesting questions to ask your boyfriend

This list of fun questions is ideal for exploring some unexplored topics that will lighten up your atmosphere with good humor and curiosity. Feel free to experiment with them. 

152. What dish would you choose if you could cook it perfectly?

153. How do you feel better when you’re having a bad day?

154. Is there any ride at an amusement park that you just have to ride?

155. Did you ever want a toy as a kid, but no one ever bought it for you?

156. Do you remember sleeping with stuffed animals as a child?

157. How would you describe the sound you love?

158. Which scents do you like the most?

159. Do you have a favorite candy?

160. Which song do you like to sing at karaoke?

161. Recess was your favorite time of day. What did you enjoy doing during recess?

162. On a rainy day, what is your favorite thing to do?

163.  Which legality still feels illegal?

164. When does something rarely go as planned?

165.  Is there anything that needs to be improved in shoes?

166.  How cool would a tree look if you had total genetic control over it?

Fun yes or no questions to ask your boyfriend

Using yes/no questions to open up a discussion is very easy as you can frame them right at the moment and also have a rapid question and answer session without much effort. Use them to boost up the energy and add some fun to your casual conversation. 

167. Are you aware of your Zodiac sign?

168. Do you recall ever being arrested?

169. How many retirement accounts do you have?

170. Do you own a home?

171. Was school enjoyable for you?

172. Your family is very important to you. Do you enjoy spending time with them?

173. Do you remember the last time you buried a time capsule?

174. Are you familiar with lucid dreams?

175. Do you have a hidden talent?

176. Do you believe that God exists?

177. Would you like to pray to God?

178. Are you convinced that we evolved from animals?

179. Are you convinced that aliens exist?

180. Is there still something you keep in your journal or diary?

181. Have you ever confused a girlfriend with someone else?

182. Have you ever lost a big bet?

183. Have you ever lost a large amount of money?

184. Were you ever a part of the “cool kids” table in high school?

185. Did you ever fall in love immediately?

186. Have you ever lied to your parents?

187. What is the most unusual thing you’ve ever done?

188. Are you familiar with multiple people with whom you have been physically in contact?

189. Have you ever eaten old sushi?

190. What is your average number of workouts per week?

Fun flirty questions to ask your boyfriend

Healthy flirting has many positive effects on the body. According to some sources, it reduces stress and enhances self-esteem. So pick up your favorite flirty questions from this list to get you excited.

191. If you are stuck in the mall for a night then what would you do? 

192. You have a magic lamp, but the thing that comes out of it isn’t a genie. How can you tell?

193. How would you react if you heard footsteps on your roof on the night before Christmas?

194. There’s either a wedding that you have to attend or your mom has to attend a wedding that you’re attending. Which will you attend?

195. If you hold your breath for 10 minutes, you will be able to keep going. What do you do when you have extra energy?

196. What kind of buried treasure would you like to find if you could find any kind of buried treasure?

197. When it comes to money, what can you do but spend it?

198. Come up with a new technological innovation.

199. How do you choose the best butter?

200. The next morning, you awake to find that everything you touch has turned into cotton candy. How do you handle it?

201. How would you spend a whole day if you had your choice of opera costumes and the whole place to yourself?

Fun questions to ask your boyfriend about yourself

Do you want to know how much your boyfriend knows about you or how observant he is? This set of fun questions will allow you to dig deep into his mind and find out a lot about yourself at the same time. Go ahead and ask them! 

202. An anonymous grant gives you the opportunity to solve one of the world’s problems. Which will you choose?

203. Have you always wished you possessed a certain talent?

204. If you have a free ticket, you can travel anywhere in the world. Which mode of transportation will you choose? Bus, train, or plane? 

205. Which exercise would you never want to do again?

206. You would become a super-genius in the field of _______ if you had incredible knowledge in one subject?

207. One thing you would change about me, what would it be?

208. What do you think is more difficult for men or women?

209.  How would you describe the most beautiful person that you have ever seen?

210. Do you know what menstruation is and why women have it?

211. Why does it appear that the sun rises and sets?

212. Name ten authors who are not male?

213. Are you still in touch with any former lovers?

214. What’s your take on the statement “once a cheater, always a cheater”? Have you ever cheated on anyone? Is it true or false?

215. What are your thoughts on Elizabeth Warren?

216. Do you remember my best outfit from the past?

217. Which of my jokes has been the funniest to you?

218. How would you describe me in one word?

219. Would you say that I am more successful in my professional life or in my personal life?

220.  Is staying at home a more appealing option for you or being a working parent?

221. What if you had someone ready to serve dinner to you every night at 6 p.m. Wouldn’t that be nice? If not, why not?

Fun questions to ask your boyfriend when your bored

The topic of conversation can become stale after a long-term relationship. You and your boyfriend will never have a dull moment when you ask him these interesting questions. Pick up the questions that excite you the most and ask him. 

222. In what city would you like to live? What would you prefer? A farm in the middle of nowhere, a house on the water, or a hip, downtown apartment?

223. When you retire, what would you like to do?

224. What would be the perfect vacation for you? Would you rather stay at an all-inclusive resort in Maui, see London, or go camping in Yosemite?

225. Which city is your favorite?

226. What skill would you like to have without having to work for it?

227. Is it possible for men and women to just be friends?

228. When you’re sick, what kind of treatment do you like? How about being left alone, or getting waiters and waitresses to take care of you?

229. Where do you draw the line when it comes to relationships?

230. Can you think of any relationship clichés that are true?

231. Which subject would you study if you were forced to return to school?

232. Which time of year is your favorite?

233. How do you stay motivated?

234. How has this year been the best year of your life so far?

235. When does your brain go into autopilot mode?

236. Do you have any idea what aliens would look like?

237.  Do you know of any websites that should exist but do not?

238.  Is there anything you wish you could eat that is inedible?

239. Have you ever danced in a crazy place?

240. Do TP rolls hang over the edge or below the edge?

241. Is there anything you’ve eaten that’s been extremely spicy?

242. Is there something silly you are very proud of?

243. Is there any unnecessary product or service that you believe is necessary?

244. Who is your favorite fictional character?

245. Are ghosts real to you?

246. Have you ever played a prank on someone? Have you ever been pranked?

247. In your opinion, what are the top three foods you would choose if you could eat only three for the rest of your life?

Random fun questions to ask your boyfriend

Randomness is good for letting you express your thoughts and go with the flow. So you can just go through this list of random questions to ask your boyfriend and ask him whatever stays on the top of your mind. Have some fun with the unplanned, random conversation!

248. What person would you trade places with if you could?

249. Which of your hidden talents are you most proud of?

250. Has it ever occurred to you that you may have had a past life?

251. When was the last time you broke a bone?

252. What tattoo would you get if you got one today?

253. How would you live in any fictional universe, whether it be from a movie, a TV show, or a book?

254. What kind of collectibles do you have?

255. How would you describe your theme song?

256. In the event that you woke up tomorrow and were fluent in any language, which language would you pick?

257. What superstitions do you have?

258. Do you think you would change anything if you had a chance to do it over again?

259. Skydiving is an exciting experience. Have you done it?

260. Do you have any experience inventing things?

261. Are you interested in going on a silent retreat?

262. What would you pick as your new name if you had the opportunity?

263. Who would you bring back to life if you could and what would you do with them?

264. If you ever become rich, what crazy things will you do?

265.  What would be the impact of health potions on the world?

266. Are you sure I would look sexy wearing glasses?

267. The best cartoon character you have ever seen?

268. What would you toss against a brick wall if you could?

269. It just so happened that you found five dollars on the ground. So now what?

270. If you lived in a cave, would you rather live under the sea?

271. Would you give me the last cookie if there were only one left?

272. What dessert would you choose if you could feed me?

273. Do you have any nasty habits you can’t seem to kick?

274. If you had a choice, would you rather have McDonald’s or a healthy meal?

275. Can you tell me about your weirdest celebrity crush?

276. Can you imagine what you’d do in zero gravity?

278. Which was the funniest social media screw-up you ever saw?

279. What would you say to someone who has something on their face?

280. Have you ever made a bad purchase?

Fun personal questions to ask your boyfriend

Are you interested in learning more about your boyfriend? These questions will help you learn much more about him you wouldn’t normally talk about. 

281. When people are stressed out, what do they really need to chill about?

282. Is there something you would find at a theme park designed especially to make you happy?

283. What everyday household item would you curse so that it would at random intervals let out a blood-curdling scream if you could curse your worst enemy?

284. How would you spend your free time if you were able to fly?

285. When you make a wish, you lose what you love most every time. How many wishes do you make, and what is on your wishlist? 

286. Can you share which condiments you refrigerate and which you keep in the cabinet or pantry?

287. Is there a great idea you would like to try if you had money to spare?

288. What song would you want on the radio if you were in a high-speed chase?

289. What would a cult look like if you started it?

290. What is your non-military experience?

291. Are there any chores you dread the most?

292. Have you ever been around a toxic person?

293. How does someone make you feel when they do gross or unhygienic things?

294. Would you like to share a habit that very few other people have?

295. When you were a kid, which movie was your first favorite?

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

297. Imagine yourself having grandchildren at some point?

298. What would be another profession you’d enjoy?

299. Which of your own physical features is your favorite?

300. When you were a child, who was your favorite teacher?

301. Your favorite mother-daughter memory?

302. When was the last time you spent time with your dad?

303. Do you have any significant others who influenced you the most before me?

304. The first time you had a sexual experience, what did you think?

305. Higher education or high school: which did you prefer?

306. When was the last time you traveled? Where would you like to go?

307. Have you ever thought about a completely different career path?

Fun love questions to ask your boyfriend 

Get close to your boyfriend by asking him these lovely questions. Making your conversation interesting and different from usual will require you to ask questions about love with a pinch of humor. Go ahead and try them out!

308. What is your favorite place to be with me?

309. Do you ever think of me when you hear a song?

310. What was it like when we first saw each other?

311. Wouldn’t it be nice if I could read your mind? Can I?

312. What about me makes you believe I’m the one for you?

313. Is there one thing that we have in common that you absolutely adore?

314. Do you have a favorite aspect of me? (Anything else besides a physical feature)?

315. How would you describe your most memorable experience?

316. Would you like to do something we’ve never done before together?

317. In your opinion, what is lacking in our relationship?

318. Which of my non-physical qualities do you like best?

319. In the event of our breakup, what is the one thing you would miss the most?

320. How would you describe the moment in our relationship that you felt most vulnerable?

321. Would you prefer a big or small wedding?

322. When it comes to showing affection, what is your favorite way?

323. Have you ever dreamed of us in the sexiest way?

324. Would you ever like to have kids and settle down?

325. Where would you want to go if we were able to go anywhere together right now?

326. Since we first started dating, how do you think we have changed?

327. Is there anything about us that has remained constant since the day we got together?

328. Do you think that we work well together? Where do we find a balance between us?

329. Do you know what love means to you?

330. Is it possible to have a picnic outside under the stars?

Dirty questions to ask your boyfriend for fun 

Adding some sexiness to the silence will make it more fun. The following list of dirty questions to ask your boyfriend will provide you with some ideas about how you can have fun while being sexy at the same time. 

331. What does it look like when you close your eyes and kiss me?

332. Is it okay with you for me to hold your hand in public?

333. Is there a place that you enjoy getting massaged the most?

334. Is it alright if I kiss you on the neck?

335. Before we actually slept together, how many times did you want to kiss me?

336. Which part of my body do you like best?

337. What do you think I am most fond of on your body?

338. When were we most romantically kissed by each other?

339. What do you think about cuddling?

340. What do you think about kissing me in public?

341. Could we ever do skinny dipping together?

342. What would you call my kissing style?

343. If you had the choice between a 5-second hug or 1-second kiss, which would you prefer?

344. How do you feel when I touch your face?

345. How about taking a bath with me sometime?

346. Which of my sexual features is your favorite?

347. When you gaze into my eyes, what do you feel?

348. Can you describe how you felt when we had our first kiss?

349. When it comes to kissing, where is your favorite spot?

350. When do you feel the horniest?

351. Can you tell me about your dirtiest fantasy?

352. When I go down on you, how does it feel?

353. What is the sexiest scene in a movie you would like us to recreate?

354. Do you ever want to rip my clothes off just for the sake of ripping them off?

355. Is there anything you want to do to me that you like?

356. Is there a position you enjoy the most with me?

Tips to ask fun questions to your boyfriend and grab his attention

In addition to the master list of fun questions, these instant tips will help you make your conversation more exciting and intimate. Sometimes you only need a gentle reminder in order to make the most of your time together while still having fun. 

1. Glow up

Your conversation can be sparked by talking, walking, and dressing in ways that create intimacy and closeness. Show off your beautiful smile while wearing an elegant outfit. The way you look up and the way you smile will naturally attract him. 

2. Dance and ask 

You can arrange a date night including some fun activity like dancing, rapid fire or other games. You can pair up your questions with any fun or romantic activity that will make the whole experience more interesting and exciting.

3. Compliment 

Compliments are fun, who doesn’t like them? Tell him how hot he looks in that outfit or something else about his personality. This will boost his self-esteem and set the right tone and mood for your conversation. Consider the details, even if they seem small, It will make him feel special. 

4. Confidence 

It’s the confidence that makes the difference. You can look into his eyes or playfully touch him in between the conversation like hugging or patting on the shoulder or kissing. It will make him feel loved and secure.

5. Give him space 

There may be times when he is not in the mood to have the conversation, and that is fine. Make yourself more comfortable by avoiding forced conversation, sometimes silence works better. Let him have some space and respect his decision. 

Over to you…

Now that you have this master list, you can easily make your conversation more engaging and fun. However, make it more personal according to your boyfriend’s interests, likes and dislikes. 

Also, avoid asking anything that may trigger unpleasant memories. Make him feel special and enjoy your time together. 

You don’t have to rush into making everything work. Take it easy and just live in the moment. It’s all about knowing your partner and having fun.