250 Good Questions to Ask a Guy the Next Time You're Feeling Stuck

Conversation starters aren't always that easy to come up with—there's a reason why small talk is a thing. But when you're on a date with someone you like, one of the last things you want to discuss is a boring topic like the weather. When in doubt, there are plenty of good questions to ask a guy to get a more interesting conversation going to keep both of you engaged.

These questions are really great to ask when you're still getting to know someone, like if you're on a first, second, or third date with a boy, and you're trying to figure out a little more about them. But they're also excellent to keep in mind even if you two have been dating for a while, and you just don't have anything to talk about over dinner. You'll learn more about each other and possibly open the door to more intimate discussions. Some questions are funny and flirty, while some are deep and really random. Here's a look at some good questions to ask a guy the next time you're feeling stuck.

Fun Questions to Ask a Guy

1. What's your all-time favorite movie that you've seen a million times?

2. What did you want your job to be when you were a kid?

3. If you could go on vacation anywhere in the world and money wasn't an issue, where would you go?

4. What would you do if you won the lottery?

5. What do you find most attractive about a woman?

6. What's the most ridiculous talent you have?

7. What is something everyone always gets wrong about you?

8. How do you relax after a stressful day?

9. Who is your role model?

10. Which celebrity would you want to meet the most?

11. What is something you've never been good at doing?

12. What is the one thing you always notice first about a woman?

13. What's your favorite childhood memory?

14. What have you done that you're most proud of?

15. What have you done that you're really not proud of?

16. What's the scariest thing you've ever done?

17. If you could be a pro at any sport, what would it be?

18. If you could marry one celebrity, who would it be?

19. Why is your best friend your best friend?

20. What do you think the best thing about being in a relationship is?

21. What's your favorite animal?

22. What's something on your bucket list you really want to do soon?

23. What's something on your bucket list you think you'll never actually do?

24. What's the weirdest thing that's ever happened to you on a date?

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

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26. Which show could you binge-watch more than once?

27. If you could domesticate any mythical creature as a pet, which one would you choose?

28. What would be the worst thing that could happen to you on a first date?

29. If you could meet one dead celebrity, who would it be?

30. Who is your favorite person to follow on Instagram?

31. What is your biggest pet peeve about dating?

32. What would you change about social media?

33. What is one thing a woman can do to instantly impress you?

34. What has been your most embarrassing moment so far?

35. What is one thing a woman can do that would instantly turn you off?

36. What is your favorite compliment to receive?

37. What makes you smile even when you've had the worst day?

38. Would you rather own dogs or cats for the rest of your life?

39. Tell me something you've never told anyone else.

40. What was your favorite candy or treat as a kid?

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41. What food would you never eat?

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

43. What do you like the most about me?

44. If you could change your job right now, what would you be?

45. Give them three words you would use to describe yourself.

46. What does your perfect date look like?

47. What is the coolest vacation you've ever taken?

48. Name one country you really want to visit.

49. Would you rather go camping or clubbing?

50. What are you most afraid of?

51. What's the nicest thing you've ever done for a woman?

52. What's the nicest thing a woman has ever done for you?

53. What is your biggest dating dealbreaker?

54. What's your earliest childhood memory?

55. What is one thing that always makes you angry?

56. What has been your greatest achievement so far?

57. What is one thing you love about where you live?

58. What is one thing you hate about where you live?

59. What's your go-to Starbucks order?

60. If you could get one gift, what would it be?

61. Do you prefer to get a physical gift, gift cards or cash?

62. Would you describe yourself as more of an introvert or an extrovert?

63. If you could re-do one moment in your life, what would it be?

64. Where is your favorite place to go when you need to relax?

65. Do you like going to the gym or working out at home?

66. What was the last thing that made you cry?

67. What's something a woman could do that you could never forgive her for?

68. Have you ever been betrayed by a friend?

69. What's your favorite thing about your friends?

70. How did you meet your best friend?

71. What question do you always ask women on a first date?

72. Do you want kids?

73. What makes you want kids?

74. What's the most trouble you've ever been in?

75. Would you rather vacation at the beach or in a cool city?

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Random Questions to Ask a Guy

76. What's your dream car?

77. What's your favorite book?

78. What's the worst movie you've ever seen?

79. Which superpower do you wish you had?

80. What's the most fun thing you've ever done with your friends?

81. Are you closer to your mom or dad?

82. Who is your favorite family member?

83. What do you think is the most impressive thing you've ever done?

84. What's your weirdest habit?

85. What's your biggest phobia?

86. What is something you would never spend money on?

87. What is something you look forward to every year?

88. Do you like winter or summer more?

89. What's something you stressed over that ended up being no big deal?

90. What do you think reveals a lot about a person you're dating?

91. Have you ever had a crush on someone who didn't like you back?

92. When do you know it's time for a woman to meet your family?

93. If you had the day off with nothing to do, how would you spend it?

94. Do you think your zodiac sign is accurate for you?

95. Have you ever lost someone close to you?

96. If you had three wishes, what would they be?

97. What was your favorite cartoon as a kid?

98. What's the grossest thing you've ever eaten?

99. Would you rather play truth or dare?

100. Describe your perfect burger.

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101. What have you done wrong for most of your life and only recently found out the right way to do it?

102. Have you ever met anyone famous?

103. Do you think you're a competitive person?

104. What's your favorite restaurant?

105. If you could learn one new skill right now, what would it be?

106. Is there a song that always brings up old memories for you?

107. If you had to pick one song to listen to on repeat, what would it be?

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108. What is something you think everyone should experience at least once in their life?

109. What have you always imagined doing with a girlfriend that you've never done?

110. Where do you think the most romantic vacation would be?

111. If you could move to any other state, which would it be?

112. If you could move to any other country, which would it be?

113. Would you rather ski/snowboard or surf?

114. What do you tell women about yourself to impress them?

115. Who would be the worst celebrity to have dinner with?

116. What small thing makes you angrier than it should?

117. What flavor combination is kind of weird but you really like it?

118. What is your most prized possession?

119. What is one thing you never get bored of?

120. Who's your favorite comedian?

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121. What show do you love that people would be shocked about if they knew?

122. If you could swap lives with any fictional character for a week, who would it be and what would you do?

123. If you had to pick, would you choose Instagram or Facebook?

124. What's something you know you're judgmental about?

125. What do you hate talking about at parties or gatherings?

126. What ice cream flavor would you eat every day if you could?

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

128. What is your favorite part of every day?

129. Would you rather give up coffee or alcohol?

130. What's the most romantic movie you can think of?

131. What would be the best gift you could get from a girlfriend?

132. What age has been your favorite so far?

133. How old were you when you had your best birthday ever?

134. Which celebrity was your very first crush?

135. How old were you when you had your first kiss?

136. How do you know when you really, really like a woman?

137. What's the most useful skill you've ever learned?

138. What is something that happened to you that's so ridiculous you wouldn't have believed it if you weren't there?

139. What is one temptation you can never resist?

140. What is your least favorite fashion trend right now?

141. What's your favorite store to shop at?

142. What was the most historic thing you witnessed in person or took part in?

143. What is one story you tell that always makes people laugh?

144. What do you do every night before bed?

145. Would you say you're a night owl or a morning person?

146. If you could travel back in time, which decade would you like to live in?

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147. What do you miss most from your childhood?

148. Who's your favorite fictional villain?

149. Would you rather watch an action/adventure movie or a comedy?

150. What's your favorite holiday?

Good Questions to Ask a Guy

151. What's one thing you're really good at cooking?

152. What's one thing you wish you were really good at cooking?

153. What meal is most comforting to you when you're having a bad day?

154. How do you know when a woman is flirting with you?

155. What is something that happened in your life that felt like the worst thing at the time, but was really the best thing in the long run?

156. What's your definition of a healthy relationship?

157. What is one thing you would tell your younger self?

158. What always makes you feel like a little kid?

159. If you had to give up one food you love, what would it be?

160. Who would you haunt if you were a ghost?

161. Do you think ghosts are real?

162. If you could be the president of the United States, what is one thing you would do?

163. What's your favorite thing to do whenever you're on vacation?

164. Would you rather relax on vacation or explore and go on adventures?

165. Would you rather give up meat or sugar?

166. If you had to give up cake or cookies, which would you give up?

167. What do you think is the worst thing about the internet?

168. What is one thing you wish you could do every morning that you never have time for?

169. Who is the most important person in your life?

170. Which movie do you hate that everyone else seems to love?

171. What are you too old for but still enjoy?

172. What was fun to do once, but you’ll never do it again?

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173. Do you collect anything?

174. What's the most meaningful gift you've ever gotten?

175. What always makes you feel sentimental?

176. What's your favorite way to flirt with a woman?

177. When was the last time a stranger did something really nice for you?

178. What's a bad movie that you love even though you know it's terrible?

179. What makes you feel positive even when everything is terrible?

180. What would you do if someone cheated on you?

181. Have you ever broken someone's heart?

182. How do you deal with people you really don't like?

183. What have you really wanted to do for a long time but haven’t done yet?

184. What is the funniest movie you have ever seen?

185. Do you like Christmas or Halloween more?

186. How would you define a good person?

187. Have you ever been addicted to anything?

188. Why do you think the divorce rate is so high?

189. What advice do you give friends going through a breakup?

190. Would you rather always be late or always be early?

191. Which animal are you most afraid of?

192. What's one personality trait that's really important to you in a woman?

193. What's one personality trait you can't stand?

194. What's your favorite city?

195. What's your favorite place to get takeout from?

196. Would you rather always be cold or always be hot?

197. Do you ever sleep naked?

198. What's your favorite scent?

199. Would you ever run a marathon?

200. If you were in the Olympics, what sport would you play?

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201. Would you rather travel with friends or a significant other?

202. If you had to pick one charity to donate to, what would it be?

203. Who would you want to play you in a movie about your life?

204. Who would you want to play your love interest in a movie about your life?

205. What do you think is the worst thing about working every day?

206. What is your biggest regret?

207. Do you believe in love at first sight?

208. Is there anything you wish you could change about your family?

209. What's the weirdest dream you've had recently?

210. What is the worst lie you ever told a girlfriend?

211. Can you tell when someone is lying to you?

212. Do you believe everyone has just one soulmate or multiple soulmates?

213. Would you rather have the power to be invisible or to read minds?

214. What is your favorite physical feature about yourself?

215. Would you rather spend a Saturday night hanging out with a woman or going out with your friends?

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216. What's your most prized possession from childhood?

217. What is one thing you hope your mother never finds out about you?

218. What is the weirdest thing you've seen in the news recently?

219. Where is the strangest place you've ever kissed someone?

220. What do you daydream about every time you're bored?

Interesting Questions to Ask a Guy

221. What is something you took for granted in your last relationship?

222. Has anyone ever walked in on you naked?

223. How would you describe me to someone who doesn't know me?

224. What's your favorite family memory?

225. What is one tradition you love the most?

226. What's your favorite reality show?

227. Do you have a favorite Kardashian/Jenner?

228. If you had to choose, would you rather be a model or an actor?

229. What did you think was silly until you tried it?

230. Would you rather go to work early and get out early, or go to work late and get out late?

231. What New Year's resolution do you always make?

232. Are you a spender or a saver?

233. Where did you learn your favorite hobby?

234. What is your dream wedding like?

235. Did you get in trouble a lot in school?

236. What's your least favorite thing about technology?

237. Who do you wish you could trade lives with?

238. What's the scariest dream you've ever had?

239. What does your perfect day look like?

240. What's the worst job you've ever had?

241. Have you ever dated a coworker?

242. Would you ever date a boss?

243. What's the worst injury you've ever had?

244. How can a woman gain your trust?

245. How many people have you seriously dated?

246. Have you ever dated someone your family hated?

247. What was one time you really stepped out of your comfort zone?

248. What is your biggest guilty pleasure?

249. If you were a superhero, what kind of secret identity would you have?

250. What makes you smile no matter what?

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Story by Jessica Booth.