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Fun Questions to Ask a Guy

Looking for fun questions to ask a guy to get him interested in you? Getting to know a guy can be tricky if you don’t know what to ask him. To figure out precisely what to ask him to strengthen your bond with him, try out these 200+ fun questions.

Let’s look at the following fun and great conversation-starter questions to ask a guy.

My experience asking relationship-building questions (of any kind)…

Before digging in… I’ve had a lot of experiences asking questions to build relationships. Whether it’s with family, friends, a guy/girl, or a coworker. Here are my top tips for asking questions of ANY kind.

  • Remember a few that you like – Keep a couple of great questions in your back pocket. My favorite, “Where’s somewhere you want to go this weekend?”
  • Don’t forget these as a tool – Whenever there’s a dull moment, whether you’re with a spouse or family… pull out a few of these questions.
  • Don’t take it too seriously – Especially when it comes to spouses. This isn’t a time to start digging! Have fun, make it silly, and don’t take it all too seriously.

P.S. I really like this YouTube video for extra help!

Best Fun Questions To Ask A Guy As A Conversation Starter

For an interesting conversation, you can ask the following fun questions and [hopefully] get funny answers. Here are some natural conversation-starter funny questions.

1. Have you ever gone to work without wearing your underwear?

2. What is the weirdest thing you have ever seen in your house?

3. What dream job have you had that makes no sense at all?

4. What will you do if you can prevent aging forever?

5. Do you use your phone while pooping?

6. What funniest moment do you remember from your last relationship?

7. How many phones do you bring with you to the toilet?

8. What is your opinion about this thing: how many dating apps should a good human being should have?

9. What random compliment made you laugh your ass off?

10. Which embarrassing thing do you remember from your past relationships?

11. Do you like your partner to do childish things?

12. What unusual thing do you wish to do with your partner?

13. What terrible movie do you like to recommend to your ex?

14. Was your past relationship healthy, or was your ex the craziest thing alive on the earth?

15. Do you think a dog person would take his dog to watch his favorite movie?

16. If you could level up, where would you have put the next skill point?

17. Do you think cheating is a big deal?

18. What is your favorite smell?

19. If you had to turn into an inanimate object, what inanimate object would you become?

20. What random acts do you prefer to do in the morning?

21. What is the most awkward thing you had in your search history?

22. What will you do if your father sees your search history?

23. Have you ever watched the worst-reviewed film that you enjoyed?

24. What is the best thing about your gender?

25. What came first, the chicken or the egg?

26. Have you ever slipped and fallen in front of a crowd?

27. Why does a dog bark?

28. What is the funniest Wi-Fi name you have had in your life?

29. Have you ever wondered if chicken but like the way your buff after having chicken?

30. Have you ever fallen asleep in between a meeting?

31. What makes you want kids?

32. What crazy adventures do you want to test in your life?

33. Do you have a smell fetish?

34. How long can you act like something or someone? But you hate the most.

35. What will you do if your ex shows up in the middle of your exciting date night?

36. Is it okay to smile while kissing?

37. What worst lie have you ever told?

38. What useless thing do you do daily?

39. What was the funniest but most unusual experience you’ve ever had?

40. Do you have any humorous nicknames?

41. Do you hang your toilet paper under or over?

42. Have you ever stolen anything from the store?

43. Have you ever read comments to pass your time?

44. What is the funniest thing you do to pass your time?

45. What funniest joke did you crack on your first date?

46. Would you like to date your toxic ex again? Or do you want to kill your ex?

47. What would you prefer most, dating your ex again or having a friendly conversation with your enemy?

48. Where was the most discomfiting place you ever have farted?

49. Do you talk to yourself out loud?

50. Has anyone ever caught you talking to yourself?

Random Fun Questions To Ask A Guy

51. What is the funniest incident of your life?

52. Do you think a magic spell is a real thing?

53. How would you like to die?

54. What would you do if your younger self could be improved?

55. Will you return to your past if you get a time machine?

56. What is the funniest password you have ever set?

57. Have you ever wondered why pizzas come in a square box but have a round shape?

58. What funny story do you have in store to impress others?

59. Have you ever made up stories to impress your date?

60. Would you like to tell the embarrassing truth? Or twist the truth?

61. Have you ever peed in a swimming pool?

62. Have you ever stolen anything from your home?

63. What weirdest thing did you ever experience in your life?

64. Have you ever been teased by others?

65. What will you do if a girl teases you?

66. Have you ever flirted with somebody you should not have flirted with?

67. Which food do you want your enemy to have?

68. Have you ever ruined meaningful conversations with your shitty topics?

69. What will you do if you wake up as your opposite gender?

70. Have you ever wondered why the sky is blue?

71. Why do roosters wake up so early in the morning?

72. Do you talk to your pets?

73. Do you believe in ghosts? Have you ever met one?

74. What flavor combination turns you off?

75. What personal goals do you wish you never had?

76. Will you be happy if you get a time machine to travel back to historical events?

77. What is your opinion on pineapple pizza?

78. Have you ever cheated on your tests?

79. Do you know how long does it take to grow hair?

80. What hidden apps do you have on your mobile?

81. What fantasy do you have in life?

82. Do you have any fetishes?

83. How did you approach your first crush? Was it funny? Or was it awesome?

84. What doubt or dilemma do you have about the universal facts?

85. Have you ever heard anything weird in your head? Or is it just me?

86. What is the dumbest thing you have ever done for self-improvement?

87. What is your favorite comedy movie?

88. Where do you want to be in an hour?

89. What is your biggest phobia?

90. What is your opinion about paranormal things?

91. Have you ever experienced any paranormal thing in your life?

92. What body part would you like to replace with a better mechanical version?

93. What fun question do you prefer to ask a gild on a first date?

94. What is the dumbest rule you had in your last relationship?

95. Do you like to ask flirty questions? Or normal conversation-starter questions on a first date?

96. Would you like to watch romantic or horror movies on a date?

97. What was the last movie you watched with your buddies?

98. Do you prefer to order your favorite food? Or the foods your partner like the most on a date?

99. What do you prefer the most in your partner: extreme kindness or horniness?

100. What weirdest sexual bucket list scares your partner the most?

Fun Sexual Questions To Ask A Guy

101. What physical characteristics do you think you are most attracted to?

102. What makes you feel good in bed?

103. What will turn you on almost instantly?

104. What position or act is overrated?

105. What is the strangest place you have ever had sex in?

106. In the case where you could have sex only in one position for the rest of your life, what would the position be?

107. What is the sexiest name you want to call your partner?

108. What do you prefer the most: sex with lights ON or sex with lights OFF?

109. What is the only thing you remember from the first time you had sex?

110. What is the most convenient method for you to masturbate: Imagination, Porn, or anything else?

111. Have you ever tried a one-night stand? How was your experience? Do you want to repeat that?

112. What is the sexiest set from a movie that turns you on every single time you watch that?

113. What is your favorite spot to be massaged while enjoying intimacy with your partner?

114. What is something you wish you had known about sex before having it for the first time in your life?

115. What is your most preferred thing on the sex bucket list at present?

116. What is the worst sex thing you have tried? And now you do not want to try again in your life ever?

117. Do you like kinky kinds of stuff?

118. What kind of porn do you prefer to watch the most?

119. What is the single thing you were utterly surprised to know about sex?

120. Do you like threesomes?

121. What do you like the most: night sex or morning sex?

122. How often do you think someone should masturbate? (this way, you can indirectly know how many times he/she does it)

123. Have you ever tried doing it outside?

124. Do you have any sex dreams?

125. Is shower sex overrated or hot?

126. Do you have any fetishes when it comes to sex?

127. When do you get the most amorous: in the evening or morning?

128. What is your preferred dirty opening line in the bed?

129. Is there something that turns you off? If yes, then what is it?

130. How long can you do without any pause?

131. Do you prefer doing it with protection? Or without protection?

132. What is the one public area where you would like to do it?

133. Do you have any friends with benefits? You know what I mean.

134. What is your dirtiest fantasy in bed?

135. What is the maximum number of times you have done it in a row?

136. What would you have done to me if we were in a room right now?

137. What is the sexiest thing you want to hear from your partner in bed?

138. What are your views on foreplay?

139. What is your opinion on friends with benefits?

140. What fantasy character do you want to try in bed with your partner?

141. If you could do anything with me, then what would you do?

142. What is the most bizarre thing you have dreamt about with a girl in bed?

143. Are you a top person or a bottom person?

144. Have you ever wanted to tear the clothes off your partner and have sex?

145. What is one thing you wish me to do in bed that no one has not done for you before?

146. How do you feel when someone goes down on you? Do you like it?

147. Is there any sexy scene that you wish to recreate with your partner?

148. What is the key to driving you crazy?

149. Do you wish to know what I am wearing right now?

150. What kind of foreplay do you like the most and want to try with me?

151. If there was one body part of me that you could touch for the rest of your life, which body part would it be? (This will help you to know which of your body part is his favorite)

152. Can you open my bra with your fingers only?

153. What is your naughtiest fantasy about me?

154. What type of lingerie do you want me to wear in bed?

155. How often do you prefer to be intimate with your partner?

Fun 21 Questions To Ask a Guy To Start A Conversation

Here is a set of fun questions you can ask a guy. These are perfect for the 21 questions game.

156. What is something that you always prefer to lie about?

157. When was the last time you laughed so hard that you cried?

158. Do you remember the dreams you have at night?

159. Would you ever do a nudie run?

160. What is the most useless talent you have?

161. If you died, would you like your spouse to marry your best friend or someone you hated?

162. Have you ever done anything embarrassing or illegal? What is it?

163. Would you jump into a pool of apple pudding or custard?

164. What are your thoughts on porn?

165. Is water wet?

166. What is the funniest vent in your life?

167. What is the funniest joke that you remember right now?

168. Do you remember your first kiss?

169. Did you ever fart in public?

170. Have you ever burped during a date night?

171. What was your funniest moment during a dating?

172. What is the funniest thing on your bucket list?

173. Which social media platform do you think has the funniest meme?

174. What weirdest habit do you think a cat person has?

175. What is the most irritating food for you? And why?

176. Which fictional character (male or female) do you pick for the video game you play in your everyday life?

Fun Questions To Ask A Guy Over Text

—Fun questions to ask over text!

177. What would you do if you were a lady for a day?

178. What is the weirdest thing you would ever do if I were with you now?

179. What is the most embarrassing story of your life that you have not shared with anyone else?

180. What is something people often get wrong about you? And you hate that the most?

181. What are the funny pick-up lines you often know to impress a girl?

182. Do you have any guilty pleasures? What are those about?

183. If you had the superpower to x-ray bodies, which part of me would you want to check out first?

184. Do you believe in the concept of love at first sight?

185. Who is the last person you want to be with you in your life?

186. If you had a magic lamp with a genie who grants you three wishes, what would you like to wish for?

187. What is the craziest thing you are ready to do to get me?

188. Who is the role model that you would want us to be like?

189. Which lesson do you want to teach girls about men?

190. Can you make small talk with a stranger? How do you do that?

191. What are you wearing now to bed?

192. Do you think a girl and a guy can be just friends?

193. What would you do if you had the chance to spend a day with your crush?

194. Have you ever fallen in love with your girl best friend?

195. Have you ever in your life flirted with a girl online? How was your experience

196. Do you think about me when I am not around? Just like now.

197. Have you ever been caught gazing at a lady?

198. What gestures or things make you the happiest if you have a bad day?

199. What’s the one thing one can do to impress you?

200. Have you ever tried to stalk anyone? Who was that?

Flirty Questions to Ask

—Fun questions to ask that are flirty!

201. Do you like massages?

202. What do you prefer the most: cuddling or kissing?

203. Do you want me to wear anything special for me?

204. Would you like to be my prince?

205. Do you think I can satisfy a handsome guy like you?

206. Which body part are you proud of the most? I think it is your biceps.

207. Do you like it if a girl takes the first move? Because I am willing to do so for you only.

208. What is the thing in me that you noticed first? I have noticed your lips. And now I can’t think of anything else.

209. What’s the wildest thing you have ever done in your life? I hope that is something interesting.

210. What turns you on? Tell me, and I will do that for you.

211. Do you prefer cuddling or making out the most? I am asking because I am available for both with you.

212. Have I ever shown up in your dreams? Because there is not a single night I don’t have dreams about you.

213. What do you find most attractive in me? I found you attractive from every angle.

214. What kind of girl are you tempted to the most? Because I am willing to be like the one, you prefer the most.

215. Do you want me to kiss you right now?

216. Can I please feel your biceps?

217. What is your opinion about having an open relationship with me?

218. You are a good kisser. Can you kiss me right now?

219. Would you like to meet me again tomorrow? Because I can’t have enough of you

220. Do you continuously think of me when we’re apart like I do?

221. Have you ever in your life wanted to tear off my clothes? Because I would love to do that with you

222. Do you feel as heavenly as I do after we make out?

223. Do I make you nervous in bed? Because often you do with your excellent performance in bed

224. Can you please tell me who your celebrity crush is? Because I want to surprise you sometime by dressing like her.

225. How high is your sex drive? I believe it is higher than anyone can think of.

226. What is the dirtiest thing you want me to do for you in bed?

227. What dirty talk do you want me to do in bed for you?

228. Would you like to recreate your favorite movie scene with me?

229. How about we do it on the couch right now?

230. Can we do it more often because I can’t get my hands off you any longer?

Dumb Funny Questions To Ask A Guy To Make His Mood Light

—Fun questions to ask that are also dumb!

  1. If I were the only person remaining on earth, what is the one thing you would do to me now?
  2. If you were in a zombie apocalypse, what would you do? And where would you hide?
  3. What do you think people do: eat soup or drink it?
  4. Have you ever thought that swimming pools are filled with strange people’s pee? Just think how gross it is.
  5. What will you do if you meet an alien now?
  6. What was the craziest thing you have ever done while being drunk as hell?
  7. Which animal would be the most disrespectful if all creatures could talk just like human beings?
  8. Which individual do you know who reminds you of your favorite cartoon character?
  9. Do you still prefer to sleep with your stuffed toy just the way you used to do in your childhood days?
  10. What do you think mermaids have: lay eggs or live babies?
  11. What is your opinion on alien existence?
  12. Will you be happy or afraid if you meet an alien now?
  13. Do you have anyone on your list whom you want to hit hard?
  14. Where would you prefer to time travel if you had a time machine now: to the future or back to your past?

How to deliver the best personal question prompt to a guy

Trying to build a connection with someone is challenging. Yes, it is! Although, here are some simple tips that can help to increase your chances of getting a positive response.

1. Be confident

Keep your prompt short and sweet. Be confident in your delivery. He’ll see that.

Related: Questions to ask a guy over text

2. Make eye contact

Don’t keep your eyes down to the left or not facing him. Make direct eye contact when asking the question.

Related: Questions girls are afraid to ask guys

3. Be prepared for a response

Fold your hands, listen closely, and let him speak. Listen carefully to the words he’s expressing and use that as your method for continuing the conversation.

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More questions for guys


Fact checked:
Board reviewed by Marianne Tomlinson, LCSW (Couples and Family Therapy). Content is rigorously reviewed by a team of qualified and experienced fact checkers. Learn more.

About the author

Ryan Sanderson (LCSW) Ryan is a game and relationship enthusiast who enjoys all things quizzes, games, fun, love, relationships, and family. He's a licensed social worker and helps families, couples, and children in need. He's spoken about love and relationships on Salon.com, Forbes, and Mirror, to name a few.

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