200+ Questions to Ask a Guy to Keep the Conversation Flowing

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Whether it’s on a first date or getting to know a male acquaintance or co-worker better, these questions to ask a guy can help you have an honest, fun, and meaningful conversation, while keeping the awkward pauses at bay.

Questions to Ask a Guy

Questions to Ask a Guy to Keep the Conversation Flowing (list of 14 questions from the article).


Keep the conversation running smoothly with some of these good and safe questions, that can inspire some thought-provoking conversations but aren’t too deep or intrusive from the get-go.

1. What’s your dream holiday destination?

2. What’s your favorite sport to watch?

3. Do you prefer to watch sports or play sports?

4. If you could choose to have one awe-inspiring talent, what talent would you pick?

5. Who’s the most interesting person you follow on social media?

6. What’s your dream car?

7. Would you ever take part in extreme sports?

8. If you could eat the dinner of your dreams for free, what starter, main, dessert, and drink would you choose?

9. Do you think your zodiac sign accurately describes you?

10. If you could move to another country, where would you choose?

11. Which movie or TV character do you think you’re most similar to?

12. What’s your morning routine?

13. What’s your evening routine?

14. Do you usually arrive early, late, or exactly on time?

15. Would you rather always be slightly too cold or slightly too hot?

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

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

18. If you could be an expert in one field, which field would you choose?

19. Is there anything you wouldn’t do for 10 million dollars?

20. If somebody was visiting your country as a tourist, where’s the first place you’d take them?

21. What is your favorite thing to spend money on?

22. If you could only eat one food for the rest of your life, what would it be?


Need an interesting question (or several) to take the conversation beyond the trivial? Give some of these thought-provoking questions a try, and see what interesting answers, exchanges, and debates you have.

23. What’s the most fascinating place you’ve ever traveled to?

24. If you had the chance to swap gender for one day, would you?

25. Would you rather lose all your memories or never be able to make new ones?

26. What’s your hidden talent?

27. What’s on your bucket list?

28. If you could pick five celebrities, dead or alive, to have at a dinner party, who would you choose?

29. What’s the best compliment you’ve ever received?

30. If you had the time and money to become amazing at one new skill, what would you choose to do?

31. What one anecdote do you tell that always makes people laugh?

32. Do you prefer traveling with friends or with a romantic partner?

33. Would you rather have the power of invisibility or telekinesis?

34. What qualities do you most appreciate in a friend?

35. Would you rather start and finish work earlier or later?

36. If you could be mentored by one influential figure from history, who would you choose?

37. What’s your favorite genre of book and why?

38. If you had the option to go back in time and live among the dinosaurs for a day, would you do it?

39. If you could time travel, would you visit the future or the past?

40. What interests do you have that would be traditionally associated with women?

41. What one fun thing are you eager to do in your life but haven’t gotten around to doing it yet?

42. What would your dream job look like?


If you feel you’re at the stage with a guy where you can both start opening up about things that are personal to you, have some of these questions ready to ask.

43. What person has had the most influence over who you are today?

44. What was your favorite movie as a child?

45. What’s your biggest pet peeve?

46. Which album gives you the most nostalgia?

47. If you have unlimited funding to start your own business, what business would you start?

48. Where do you see your life in ten years’ time?

49. What’s your main life goal?

50. Which film is your biggest guilty pleasure?

51. Are you closer to your family or friends?

52. Are you a competitive person?

53. What’s your most prized possession?

54. What achievement are you proudest of?

55. At a party, do you flock to the center of the room or do you stay in the corners?

56. What untrue assumptions do people tend to make about you?

57. When was the last time you spent more than 12 hours away from your phone?

58. What’s your favorite thing to do on the weekend?

59. If you could only eat one cuisine ever again, which cuisine would you choose?

60. What’s your favorite memory from childhood?

61. What’s your favorite piece of trivia to impress your dinner guests with?

62. Do you prefer to drink beer or wine?

63. Who do you speak to when you need to get something off your chest?

64. What’s your favorite song to dance to?

65. If you could only drink coffee or tea ever again, which would you choose?

66. Are you a spiritual person, and do you believe in an afterlife?

67. What is the one song that helps you get through difficult times?

68. Do you have any regrets about a past relationship?

Flirty and Playful

Feel like there’s a spark between you and want to take the conversation to a fun, flirty, and more intimate place? Get things for things to get more than a little hot under the collar with some of these flirty questions to ask a guy.

69. Do you prefer kissing or cuddling?

70. Who’s your celebrity crush now?

71. Which celebrity was your first crush?

72. Do you have a ‘type’?

73. When was your first kiss?

74. What’s your best chat-up line? 

75. What thing do you notice first about your preferred gender?

76. What’s your favorite song to make out to?

77. What’s an instant turn-off for you?

78. What’s an instant turn-on for you?

79. Do you believe in love at first sight?

80. What’s the best gift you’ve ever bought a romantic partner?

81. What’s your favorite thing about being in a relationship?

82. What’s your dream honeymoon destination?

83. How do you know when you’re in love?

84. What’s the most romantic thing you’ve ever done for someone?

85. What’s your dream gift from a romantic partner?

86. What do you think is your best physical feature?

87. Have you ever had a crush on somebody you worked with?

88. What did all your ex-partners have in common?

89. What’s your favorite body part of your preferred gender?

90. What does love mean to you?

91. When was the last time you felt butterflies when meeting somebody?

92. Would you rather spend a summer’s night lying under the stars or out partying?

93. Have you ever been skinny dipping? If so, when? If not, would you?

First-Date Questions

If you’re eager from the off to figure out if there’s any chemistry and potential between you and a guy you’re about to meet for the first time, have some of these first-date questions ready to ask.

94. What qualities do you look for in a potential partner?

95. Where do you think is the most romantic holiday destination?

96. What’s one question you always ask on a first date?

97. What would your dream date look like?

98. What are your career plans?

99. How many previous relationships have you had?

100. Do you want kids someday?

101. What are your goals for the future?

102. Do you want to get married at some point?

103. What’s on your bucket list to do with your future partner?

104. What’s the worst date you’ve ever been on?

105. What’s a dealbreaker for you with a potential partner?

106. Do you believe in soul mates?

107. How do you know when it’s time for a partner to meet your family?

108. What’s the most embarrassing thing you’ve ever done on a date?

109. Where do you see yourself in ten years’ time?

110. Are you an introvert or an extrovert?

111. Are you always honest in a relationship?

112. What do you like to do in your spare time?

113. What’s something you always imagined doing with a partner that you haven’t done yet?

114. What’s your favorite dish to cook?

115. If we were to go on a second date, where would you take me?

116. What would your ideal relationship look like?

117. Would you let your partner have their dream wedding, or do you think it needs to be a two-way thing?

118. Want some more questions in your back pocket? Take a look at our first date questions list, and see if any inspire you.

Read more: Best First Date Questions to Ask (the Ultimate List)

Open-Ended Questions

Take the conversation into uncharted waters and see what fascinating things you can learn about each other by posing some of these open-ended questions to the guy you’re talking to.

119. What are your favorite things to do in your free time?

120. How would you describe your personality in three words?

121. When you feel stressed, how do you relax?

122. How would your friends describe you?

123. What would your dream holiday look like?

124. What are your main ambitions in life?

125. Which age has been your favorite so far, and why?

126. What advice would you give to your younger self?

127. What five things in your life are you most grateful for?

128. What was the last random act of kindness you did for somebody?

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

130. What are your favorite things about the country you live in?

131. If you never had to work again, what would you do with your free time?

132. If you could design and build your dream home, what would it look like?

133. What purchase did you waste the most money on?

134. When you’re daydreaming, what things do you daydream about?

135. If you had all the money in the world, what would you do with it?

136. If I gave you a million dollars today but you had to spend it in 24 hours, how would you spend it?

Simple and Easy

Don’t want to think too much? Want to keep the conversation light-hearted and straightforward? These simple and easy questions can be answered in one or two words, and nearly everyone should have an answer to them.

137. What’s your favorite movie?

138. What’s your go-to comfort food after a stressful day?

139. If you had to give up either chocolate or candy, which would you choose?

140. Do you have any siblings?

141. What was your favorite subject at school?

142. Do you have any tattoos?

143. Have you ever dyed your hair a different color?

144. Have you ever had a pet?

145. Are you a cat person or a dog person?

146. Are you a morning person or a night person?

147. Are you vegetarian/vegan or have you ever been?

148. Can you play any musical instruments?

149. Do you have any piercings?

150. Do you speak any foreign languages? If not, which language would you love to learn?

151. What’s the best book you’ve ever read?

152. What’s your favorite animal?

153. If you could only ever eat one flavor of ice cream again, which flavor would you pick?

154. Have you ever broken a bone?

155. How often do you work out?

156. Have you ever been to a festival?

157. Who was the first musical artist you ever saw live in concert?

158. What was your favorite cartoon as a child?

159. Do you sing in the shower?

160. If you could only eat one meal ever again (without putting weight on), which would you choose?

161. Do you prefer staycations or traveling abroad?

162. Which fictional character from TV, film, or literature would you like to be, and why?

163. What is your favorite ice cream flavor?

164. How many phones do you have, and why?

165. What is the weirdest thing that has ever happened to you?

166. What is your favorite video game, either from the past or a game you play today?


Ready for plenty of laughs and some rib-tickling funny stories? Put both your senses of humor to the test with some of these funny questions to ask a guy.

167. Would you rather have fingers for toes or toes for fingers?

168. What’s the funniest movie you have ever watched?

169. What’s the worst outfit you’ve ever worn?

170. What’s the worst haircut you’ve ever had?

171. What’s the silliest thing you’ve got into trouble for?

172. What’s the funniest prank you’ve ever pulled?

173. What’s your most embarrassing moment ever?

174. What strange combination do you love?

175. What song do you rock on karaoke?

176. What’s your weirdest habit?

177. What habit annoys you the most in others?

178. What’s the worst job you’ve ever had?

179. If a genie gave you three wishes, what would you wish for?

180. What’s the most disgusting thing you’ve ever eaten?

181. Who would be the most irritating celebrity to have dinner with?

182. What’s your least favorite current fashion trend?

183. Which movie would you never watch again, even if somebody paid you?

184. What childish things do you still enjoy?

185. What’s the most useless skill or talent you have?

Deep & Thought-Provoking

Eager to get to know a guy on a much deeper, more intimate level? These deep and thought-provoking questions are ideal for intriguing conversations that can have you both opening up and finding out about each other for hours on end.

186. What’s your relationship with your family like?

187. If you had the chance to go back in time ten years, what would you change about the way you lived? 

188. If a clone was made with the exact same personality as you, would you get along with them?

189. What is your biggest fear, and why are you so afraid of it?

190. Are you religious or spiritual?

191. If you were given 1 million pounds to live in any city around the world for a year, where would you choose?

192. Would you rather be fluent in every language or be able to speak to animals?

193. What makes you insecure?

194. Have you ever had your heart broken? 

195. Have you ever broken someone’s heart?

196. Have you ever lost somebody close to you? How did it impact you?

197. What is something you’ve experienced that you think everybody should have the opportunity to do?

198. What is something illegal that you think should be legal?

199. What is something legal that you think should be illegal?

200. Do you think social media has more positive or more negative impacts on the world?

201. Do you think white lies do more good or more harm?

202. If you were made President for the day, what laws would you enact?

203. If you had to dedicate your life to one cause, which cause would you choose?

204. Do you think people have become too materialistic?

205. What negative assumptions do people make about your gender?

206. If you could find out how and when you’ll die, would you want to know?

207. What positive assumptions do people make about your gender?

208. How would you summarise your life in three words?

209. If you could have dinner with one historical figure, who would you pick and why?

210. Feel free to get inspired with some more thought-provoking questions from our list of deep questions, with over 200 ideas to choose from.

More Questions

Still looking to have more questions in your back pocket? See if any of these random questions to ask a guy are worth having on-hand in case the conversation is stalling.

211. What’s your go-to order at McDonald’s?

212. Which celebrity do you look up to the most?

213. Would you rather go on a two-week holiday to New York or Los Angeles?

214. Who’s your favorite musical artist?

215. What movie could you watch again and again?

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

217. What’s your favorite podcast?

218. What’s your favorite season?

219. What event do you look forward to every year?

220. When you play truth or dare, which do you usually opt for?

221. Do you prefer to travel by train, plane, or car?

222. Which album can you listen to repeatedly without getting sick of it?

223. What you rather give up alcohol or caffeine?

224. Are you an early bird or a night owl?

225. Who’s your favorite fictional hero?

226. Who’s your favorite fictional villain?

227. What movie do you hate that everybody else seems to love?

228. What movie do you love that everybody else seems to hate?

229. Did you get into a lot of trouble at school or were you well-behaved?

230. How did you get into your favorite hobby?

231. What are you tired of hearing about?

232. What’s your favorite fashion trend from the last ten years?

233. What’s the first thing people tend to notice about you?

Fun, intriguing, and flowing conversation needs to be a two-way street, and more often than not it needs a few prompts to lead it in the right direction.

From first dates to team-building days, sometimes it can be really overwhelming and difficult to strike up a conversation with a guy that allows you to both get to know each other better.

These questions to ask a guy are great to have in the back of your mind so that you can find out more about him and lead the conversation in places you feel comfortable talking about.

Whether you’re meeting for the first time, want to add a little humor to the exchange, or are eager to know him on a deeper level, these questions should give you the confidence and subject matter to strike up a conversation you both enjoy and get involved in.

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Got a first date, activity, or get-together coming up? Keep these questions to ask a guy in a safe place by saving them to one of your Pinterest boards.

Questions to Ask a Guy to Keep the Conversation Flowing (list of 14 questions from the article)