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Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

When you’re on a date, the last thing you want to talk about is the weather. But, there are times when you simply don’t know how to keep the conversation going. You start freaking out and asking stuff like “Do you prefer when it’s sunny or cold?” What questions are you supposed to ask a guy!?

Don’t worry, this happens to the best of us. Whether you’re chatting with your cute neighbor or enjoying the first date with your colleague from work, there’s pretty much nothing you can do when you’re brain decides to go blank.

Or, is there!? People always say that the key to keeping the conversation going is asking interesting questions. When your cute neighbor says something, anything really, you listen and ask him something related to what he just said.

It’s pretty easy when you think about it. Let’s say he mentions how he has to take his dog for a walk later that day. You can ask him what kind of a dog he has or where he typically takes his dog for a walk. You can even throw a casual “don’t you just adore dogs” into the mix.

Let’s just say you made the right call when you decided to look up questions to ask a guy. There’s pretty much no better way to start a conversation, keep it going, or just generally spice it up when things become boring.

So, if you’re running out of ideas, we’ve got you covered!

Questions to ask a guy when you’re texting

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

Oh, the art of flirting over a simple text! Once you figure out how to make a guy blush by sending him the right combination of words, there will be nothing in this world you won’t be able to achieve. Trust me, flirting over a simple text isn’t for the faint of heart.

One wrongly interpreted emoji can undo everything you’ve done up to that moment. One wrongly worded question can become a source of confusion and bewilderment. Let’s be honest, you can only text “what’s up” and receive a response so many times.

But, there’s still hope for you! There are so many interesting questions you can ask a guy to get the conversation going or to steer the conversation in the direction you want it to go. Grab your phone and get to work, why don’t you?

Start with simple questions

1. What’s your favorite movie that you could watch every single day for the rest of your life?

2. Where would you like to travel to once you have enough money to go to any destination in the world?

3. What do you like to do after a long day at work?

4. What kind of music do you listen to after a long day at work?

5. What’s the most embarrassing story that hasn’t seen the light of the day until this moment?

6. What’s the weirdest thing you can do with your body?

7. What’s the most useless talent you have?

8. Who is the one celebrity you would love to meet before you die? +

9. Who is the one celebrity you would love to take out on a date?

10. Who is the one celebrity you would leave your girlfriend for? (This one can be quite tricky, but you can always laugh it off.)

11. What’s the worst thing you’ve ever done?

12. What’s the scariest thing you’ve ever done?

13. While we’re on the topic, what is the scariest thing that has ever happened to you?

14. What’s your favorite animal and how can you say anything other than “a dog?”

15. What’s your favorite type of meat? (Skip this one if he’s vegan.)

16. What do you always lie about on your resume?

17. What do you always lie about when you’re talking to a beautiful girl you’re interested in dating?

18. What question makes a guy more interested in a girl?

19. What’s the weirdest thing someone has ever said to you over text?

20. What’s the weirdest thing you have ever said over text?

21. What’s the first thing on your bucket list?

Make things more interesting with deep questions

22. What question do you ask a guy who’s planning on taking you out on a date?

23. What about your physical appearance makes you insecure? You don’t have to send any pictures, lol.

24. What’s the one thing about a girl’s physical appearance that would make you fall for her instantly?

25. What is the one thing you would never tolerate about a girl’s physical appearance?

26. What’s the earliest childhood memory you can recall right now?

27. What’s the best thing about your childhood?

28. What’s your relationship with your childhood friends?

29. What’s your relationship with your ex-girlfriend (or ex-girlfriends)?

30. What’s the most annoying question you’ve ever been asked?

31. What’s the most amazing question you’ve ever been asked?

32. What’s the one thing you can’t imagine your life without?

33. Who’s the one person you can’t imagine your life without?

34. Would you change anything about yourself, and if you would, what would it be?

35. Would you change anything about yourself if someone else asked you to?

36. How would you describe yourself using only one word?

37. How would your friends describe you using only one word?

38. What’s one thing that’s a definite deal-breaker when it comes to the girl you’re planning on dating?

39. What’s the most intimidating thing when it comes to a girl you’re planning on dating?

40. What’s the most intimidating question a girl can ask a guy?

41. What’s one intimidating question you would like to ask a girl?

42. Have you ever lied to get something you really want from a girl, or from anyone else for that matter?

43. Have you ever done something you’ve grown to become really ashamed of?

44. Who’s your spirit animal?

45. Who do you look up to the most?

Spice things up with flirty questions

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

46. What do you think is the most beautiful thing about you?

47. What’s the most attractive thing about me? (Feel free to send a selfie at this point.)

48. What’s the most attractive thing a girl can do?

49. What do you think of a girl who makes the first move?

50. Do you like when a girl makes the first move?

51. What would you do if I sent you a kissing emoji right now?

52. What question does a girl ask a guy when she wants to receive a kissing emoji?

53. What are the three body parts you find the most attractive about me? (You could send a full-body selfie when you ask this.)

54. What do you think about my outfit? (Feel free to send a full-body selfie wearing your favorite outfit.)

55. Where would you take me if you were taking me on our first date?

56. What would you wear on our first date?

57. What’s your outfit of the day looking like? (Hopefully, he sends a full-body selfie!)

58. What are you thinking about right now?

59. What would you be thinking about if I was there?

60. What would you be doing if I was there?

61. What’s your favorite sleeping position?

62. Do you prefer being the big spoon or the little spoon?

63. Do you prefer sleeping alone or next to someone?

64. Do you believe in love at first sight?

65. And, do you believe in love at first text?

66. Would you rather be complimented on your physical appearance or your academic achievement? (Compliment him on whatever he chooses.)

67. Would you say you’re more attracted to beauty or brains? (He gets extra points if he says both and sends you a cheeky emoji.)

Questions to ask a guy when you’re talking in person

Let’s be honest, very few people in today’s day and age find frisky face-to-face conversations easier than charming your way into someone’s life over text. But, there are times when you simply have to use your best efforts to sweep a guy off his feet while he’s sitting right across from you.

Unless you want to make him regret his decision to approach you, you might want to use something a bit more thought-out than “what’s up” and “how are things?” There’s hardly anything interesting he can respond to these questions!

Instead, hit him with your best “what’s one thing you can’t imagine your life without?” and watch him go on an entire rant about how he can’t go one day without his favorite cup of coffee, or how he can’t achieve anything without his trusty laptop. That’s so much better, don’t you think!?

Before you start panicking because you’re out of ideas on what questions to ask a guy, we’ve got your back. Here are a couple of questions to help you save the day (and maybe even score a date). Let’s dive in!

Conversation-starter questions other than “what’s up”

68. What’s the one thing that puts a smile on your face regardless of how you were feeling beforehand?

69. What’s the one thing that always makes you laugh?

70. What achievement in your life are you most proud of?

71. What three things would you bring with you if you had to move to another country?

72. What three things are the most important in your life at this moment?

73. What do you value the most in your life?

74. What’s more important to you: family or friends?

75. What is the one thing you’re most passionate about?

76. What is one thing you could do for the rest of your life?

77. What’s the hardest thing you’ve ever done in your life, physically speaking?

78. What’s the hardest thing you’ve ever done in your life, mentally speaking?

79. What defines you as a person?

80. What keeps you going every day?

81. What makes you wake up in the morning, look in the mirror, and say “I’ve got this”?

82. Who’s the most inspirational person you’ve ever had the pleasure of talking with?

83. Who’s the least inspirational person you’ve ever had the displeasure of talking with?

84. What’s the most attractive quality a girl can possess?

85. What’s the most attractive quality a man can possess? (This gives you the opportunity to compliment him.)

86. What do you look for in a potential girlfriend?

87. What do you consider a deal-breaker in a potential girlfriend?

88. What’s your favorite thing to do in your free time?

89. What’s your favorite Instagram account to follow?

90. What’s your favorite TikTok account to follow?

91. What’s one thing you always wanted to do but never had the opportunity to?

Set the tone of the conversation with thought-provoking questions

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

92. Do you ever double-text or even triple-text?

93. Do you think double-texting is a deal-breaker in a relationship?

94. What’s your opinion on girls who like to text first?

95. What’s the worst thing a girl has ever texted you?

96. What’s the most embarrassing thing you’ve ever done to get a girl’s attention?

97. What’s the most embarrassing pick-up line you’ve ever used on a girl?

98. What’s the most embarrassing pick-up line you’re planning to use on me?

99. What was your first kiss like?

100. When did you have your first kiss? (Bonus points if he remembers who it was with.)

101. What’s the most spontaneous thing you’ve ever done with your friends?

102. What’s the most romantic thing you’ve ever done to get a girl’s attention?

103. What’s the most caring thing you’ve ever done for your friends?

104. Have you ever cheated on a girl?

105. Have you ever been cheated on?

106. What’s the best question to ask a guy when you’re trying to get his attention?

107. What’s the best thing to do when you’re trying to get a guy’s attention?

108. How do you know if your efforts to get a guy’s attention are working? (Bonus if you wink!)

109. What does your dream date look like?

110. What is your love language?

111. What makes you say “she’s the one”?

112. If your life was a movie, what would be the title?

113. If your life was a movie, who would play the main role?

114. If you were a dog, what breed would you be?

115. If you could have any dog in the world, what dog would you have?

116. If you could be with anyone in the world, who would you be with?

Control the direction of the conversation with gripping questions

117. What has been the best moment in your life so far?

118. What’s one thing you enjoyed doing as a child that you still secretly do? Mine’s eating Nutella straight from the jar!

119. Who’s the one person you really dislike?

120. Who’s one person you lost respect for?

121. Who’s the one person in your family you don’t like seeing on your doorstep?

122. What was the biggest fight you’ve ever had in your life?

123. What was the biggest fight you’ve ever had with one of your ex-girlfriends?

124. What’s the best thing about being a guy?

125. What’s the best thing about being a guy who gets asked a lot of questions by the girl who thinks he’s cute? (If this makes him smile, you’re in the game!)

126. What’s the worst thing about being a guy?

127. What’s one thing about you people always get wrong?

128. What would you do for 10 million dollars?

129. What would you NOT do for 10 million dollars?

130. What’s the most stressful situation you’ve ever been in and how did you handle it?

131. What’s the most stressful situation you’ve ever been in that turned out to be not that big of a deal?

132. What song are you really tired of hearing on the radio?

133. What’s one song that makes you turn the volume up every time it comes on?

134. What’s one song that makes you emotional every time it comes on?

135. What’s your opinion on double standards? (Bonus points if he’s not the perfect example of toxic masculinity.)

136. What double standard do you consider utterly ridiculous?

137. What’s one question you can ask a guy to find out everything you need to know about him?

Questions to ask a guy when you’re on a date

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

Maybe you’ve been feeling like the heart eye emoji about this guy for quite some time or you’ve had one of your friends set you up on a blind date. Either way, you have no idea how to brush up on your flirting techniques and make this guy go bonkers over you.

You’ve seen endless romantic comedies where the main character, a gorgeous Blake-Lively-esque blonde, knows exactly what to say to make the guy fall head over heels in love with her in a matter of minutes. How on earth can you compete with Blake Lively?

Besides saying something along the lines of “I like you, I really hope you like me back, can we do this again sometime?” there are other ways to score a second date. You just need a set of carefully thought-out questions to ask a guy when you’re feeling like giving up on your flirting techniques.

Surprise him with riveting questions

138. If you could become an expert in pretty much anything in the world, what would it be?

139. If they were making a movie based on your life, what would be the biggest highlights you’d want them to include?

140. What’s one thing you’re most grateful for in your life?

141. What was the worst thing you’ve ever bought?

142. What was the best thing you’ve ever bought?

143. What’s the most money you’ve spent on something?

144. What’s on top of your “to-buy” list at the moment?

145. What’s one thing you considered silly until you tried it?

146. What’s one thing you considered amazing until you tried it?

147. When you’re asleep, do you dream about anything? (If he answers yes, ask him the next question.)

148. What’s the weirdest dream you’ve ever had?

149. What did you dream about last night? Or what was the last dream you had?

150. What’s the last photo you took on your phone?

151. What’s the best photo you took on your phone?

152. What’s the weirdest photo you took on your phone?

153. What do you believe in, even though you know you’re wrong? I believe in Santa Claus and I don’t care what anyone else has to say about it!

154. What do you tell yourself when you’re in an argument and you realize you’re the one who’s wrong?

155. What’s one thing you would like to change about yourself before it’s too late?

156. What’s your favorite thing to do when you’re alone?

157. Are you one of those people who despise spending time alone?

Grip his attention with compelling questions

158. Are you one of those people who can’t imagine having coffee in a cafe by themselves or going on a trip by themselves, or are you the opposite?

159. What would you do if you were alone with me, though? (Bonus if you give him a little wink.)

160. Do you like playing pranks on people?

161. What’s the best prank you’ve pulled off successfully?

162. What’s one thing you always have time for?

163. Who’s one person you always have time for?

164. What’s the best question you can ask a guy if you want to secure a second date? (Bonus points for him if he answers “this one.”)

165. What’s something you would never spend too much money on?

166. What’s something you would always spend a lot of money on?

167. Are you a Samsung or an iPhone type of guy?

168. Are you a professional camera or phone camera type of guy?

169. What’s the most amount of photos you’ve taken in one day?

170. And what’s the most amount of photos you’ve posted in one day?

171. Does the number of Instagram followers a girl has matter?

172. Do you prefer when a girl has a lot of followers or when she has only a couple of good friends?

173. What’s the most amount of time you’ve spent online in one day?

174. What’s the most amount of time you’ve spent scrolling through Instagram and TikTok in one day?

175. Are you addicted to anything? I’d say I’m addicted to coffee, so choose your answer wisely. (Add a wink.)

176. Are you a hot coffee or an iced coffee type of guy?

177. What’s on your mind right now?

178. What’s one thing you’d love to talk about but you’re too embarrassed to ask?

Help him make up his mind with cheeky questions

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

179. What’s on your mind when you’re trying to fall asleep?

180. What are you thinking about when you stare off into the distance while everyone around you keeps raving about something unimportant?

181. What’s the first thing that comes to your mind when you look at me?

182. What’s one secret you’d share with me if I asked you politely?

183. What’s your dream venue for a second date?

184. What’s your favorite thing to do on a second date?

185. What does a girl like me have to ask a guy like you to get invited on a second date?

186. What’s your advice on what questions to ask a guy on a second date?

187. What’s one thing you’ve had on your mind the entire night? This is your only opportunity to spill the beans.

188. What does it feel like to be that good-looking?

189. Do you have girls throwing themselves at you wherever you go? Because I’m about to!

190. What’s one thing you’d like to know about me but you’re too hesitant to ask?

191. What’s one thing you’d like to do with me but you’re too embarrassed to ask?

192. How do you like your eggs in the morning, scrambled or sunny side up?

193. How do you like to start your day off, with a long stretch or a long cuddle session?

194. What plans do you have for the morning and can they be canceled?

195. What’s the reason you’re single right now and what can a girl do to change that?

196. What’s better in your opinion: asking a girl on a second date or waiting for her to ask you?

197. What would you say if a girl kissed you right now? What would you do if that girl was me?

Questions to ask a guy when you’re trying to check if he likes you

No matter how confident you are, figuring out whether a guy likes you or not can be soooo confusing. You start reading into every accidental brush of the hand, spontaneous “you look beautiful” comment, and unexpected Instagram like after you’ve gone on only a couple of dates.

Regardless of your parent’s dating advice, your very-single friend’s take on what he meant when he said “you’d love my mother,” and your astrological compatibility, deciphering a guy’s signs and signals can seem pretty much impossible. But, we’ve got your back!

Since we seem to have gone on a quest to find the deepest question you can ask a guy, we’re keeping it pretty light-hearted and fun with the last set of frisky questions you can ask when you’re trying to check if he really likes you. So, let’s get to work!

Test the waters with endearing questions

198. What’s your zodiac sign? I’m sensing we might be compatible!

199. What’s your deal with astrology? Do you like reading your horoscope from time to time, or are you completely against it?

200. What’s the most spontaneous thing you’ve ever done? Maybe we can change your answer together!

201. What’s the best date you’ve ever been on? (Bonus points for him if he answers “this one.”)

202. What’s one thing you wish you could do on a date with someone you really like?

203. What would you do if I told you I could make one of your wishes come true?

204. What’s a dating red flag you wouldn’t ignore under any circumstances?

205. Have you noticed any red flags on this date?

206. Well, have you noticed any green flags on this date?

207. Do you know what your love language is?

208. What do you think my love language is?

209. Have you ever considered love languages an important part of a relationship?

210. What was your first impression of me?

211. Was your first impression of me right or wrong?

212. What’s your favorite thing about me?

213. What’s your least favorite thing about me?

214. What’s the most attractive thing about me?

215. What’s one thing you would like to change about me?

216. What’s the reason you’re not in a relationship right now?

217. What’s the best thing about being in a relationship with you?

218. What’s the worst thing about being in a relationship with you?

219. How would your ex-girlfriend describe you in three words?

220. How would you describe your ex-girlfriend in three words?

221. How would you describe me in three words?

222. Would you describe yourself as emotional or emotionless?

223. Would you describe yourself as an alpha or a beta man?

Steer him in the right direction with charming questions

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters

224. Where do you see me in 5 years? (Wink!)

225. What would your mother think about me if she ever had the opportunity to meet me?

226. Do you think your friends would like me if they ever had the opportunity to meet me?

227. What would your dog think if you brought a girl home tonight?

228. What would your cat think if we went back to your place tonight?

229. What’s your favorite drink to offer a girl when she comes over?

230. What drawer are you comfortable giving up for a girl when things get serious?

231. What’s your biggest accomplishment, relationship-wise?

232. What’s the best way to spice things up in a relationship?

233. Where would you take me on a date on the off-chance you figured out you really liked me? (Confused wink!)

234. Do you have a type when talking about girls you’d like to date or be in a relationship with?

235. Do you have a crush on someone right now? (Bonus points if you throw a little “do I know her?” into the conversation.)

236. Do you have plans to date someone in the near future?

237. When was the last time you dated someone? Or when was the last time you were in a relationship with someone?

238. What’s one thing that would make you go “yeah, this girl has to be my girlfriend”?

239. What’s the movie you would pick for a first date with someone?

240. What’s the place you would pick for a first date with someone?

241. Where have you been all my life?

242. How does a girl attract someone like you?

Seal the deal with sweet questions

243. Have you been working out lately? (Instant mood booster)

244. Has it been difficult for you to ward off all these girls waiting for you to pay attention to them?

245. How fast did you have to run away from all these girls chasing you just to arrive here on time?

246. What does a girl have to do to deal with all these other girls competing for your attention?

247. Are you trying to flirt with me or are you this adorable all the time?

248. Are you trying to make me fall for you or are you this charming with all your friends?

249. Do you have a license to carry those guns? (Bonus points if you take the opportunity to touch his biceps)

250. What’s your idea of a perfect date? That sounds great, but do you really think I’d like it?

251. Are you taking me out of that friend zone or what?

252. Are you telling me that there’s another way to a guy’s heart that isn’t through his stomach!? Who would’ve thought?

253. What’s the best kiss you’ve ever had and would you like me to change that?

254. What would you think of a girl if she made the first move?

255. Have you ever had a dream about me?

256. Have you ever been nervous around me?

257. Do you think you have what it takes to be with a girl like me?

258. Do you have something borrowed, something blue, something old, and something new to wear to our wedding?

259. Do you feel the chemistry between us or should I make it more obvious?

260. Do you look this attractive when you wake up in the morning or do I need to check for myself?

Questions To Ask A Guy: 250+ Most Interesting Conversation Starters