250 Questions to Ask a Guy Over Text / IRL

250 Questions to Ask a Guy Over Text / IRL

questions to ask a guy

Are you looking for interesting questions to ask a guy? Well, this article is for you.

It contains witty and interesting Friday jokes and questions to kickstart a sweet conversation and give you a chance to better understand the man he is.

Whether it is a boyfriend, a crush, a new guy you met at the gala, or the guy next door, this article has enough questions for you to ask him over a text message or in real life.

General Questions

— Random Questions to ask a guy

1. Who is John Luke?

2. What are your personal goals in life?

3. What makes a lady beautiful?

4. What makes you insecure?

5. What would you expect from a lady you love?

6. What are you most proud of?

Next: 160+ Questions to Get to Know Someone

7. What brings a smile to your face?

8. What are your life accomplishments so far?

9. What is your greatest fear?

10. Do money and finances affect relationships?

Next: 100 Good Questions to Ask Your Crush

11. What childish thing do you still find exciting?

12. What movie genre are you into?

13. What is the best thing about being male?

14. What music gets you in a good mood?

15. What is the worst thing about being a man?

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16. Are women equal in all aspects to men?

17. What is your last charitable action?

18. What did you want to become growing up?

19. What is your favorite pet?

20. Who do people sometimes mistake you for?

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21. What is your favorite car?

22. What sport do you follow?

23. What sport do you play?

24. How do you feel working for…?

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25. What is your take on entrepreneurship?

26. What money lessons have you learned from the past?

27. What is your take on having a family?

28. What book did you read last?

29. Which book has had the biggest impact on your life?

30. Is it ethical to have lots of money and wealth while poverty levels are rising?

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31. What do you wish you could stop?

32. What is your definition of beauty in a lady?

33. What is your love language?

34. What do you expect from a relationship?

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35. Are you an introvert or an extrovert?

36. What do you find most attractive in a woman?

37. What do you do on free weekends?

38. Where do you see yourself in the next five years?

39. What are your long-term career goals?

40. Who is your best friend?

Next: 100+ Questions to Ask Your Boyfriend

41. Do you have an active money-saving plan?

42. What is your personality type?

43. Are you an outdoor or an indoor person?

44. How did you handle your last heartbreak, if any?

45. Where would you like to build your retirement home?

Next: 100+ Questions to Ask Your Partner

46. Is a loan a good thing?

47. What is your secret personal finance management?

48. What are you most proud of right now?

49. What accomplishments can be attributed to you?

50. What is your favorite computer game?

Next: 150+ Thoughtful Questions About Life

First Date Questions

— Personal questions to ask a guy to get to know him deeper

51. How often do you play computer games?

52. How will you describe yourself in three words?

53. What are your hobbies?

54. How much do you like traveling?

55. How much money is enough money for you?

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56. How is your bucket list for the year like?

57. Have you ever saved someone’s life?

58. What is the scariest thing you have ever done?

59. What is the greatest risk you have ever taken?

60. What do you find most exciting right now?

61. What is your best movie of all time?

62. Which TV show do you watch?

63. Whose life do you admire?

64. What makes you feel like going to the gym more often?

65. How often do you keep a journal?

66. Have you written something in the past?

67. What are you most passionate about?

68. What are some of your nicknames from the past?

69. What defines who you are?

70. What are your future savings and investment plans?

71. How religious are you?

72. What are some of the cultures that are important to you?

73. What is the best place you have traveled to?

74. Where would you wish to travel to?

75. What is a waste of time and money?

76. Which industry do you feel is cool to work in?

77. Which company do you wish to work for?

78. How often do you drink?

79. What is your go-to drink?

80. What is a turn-off for you?

81. What bad habits do you wish to stop?

82. What is your ideal first date like?

83. How proud are you of the schools you went to?

84. What is your zodiac sign?

85. How much does zodiac compatibility affect relationships?

86. What accent do you find exciting?

87. Do you use cologne?

88. Is a joint bank account for couples a good thing?

89. What is your favorite perfume scent?

90. What is your go-to designer brand?

91. Must someone have a reason to love?

92. Who is your role model?

93. What are some of your favorite blogs?

94. Have you ever run a blog or a website?

95. Do you have passive income streams in place?

96. How do you deal with heartbreak?

97. How do you deal with the loss of a loved one?

98. What do you want to do but haven’t tried yet?

99. What is your favorite vacation destination?

100. What turns you on?

Romantic Questions

— 21 questions to ask a guy flirty

101. What is the most interesting thing about your job?

102. What type of relationship are you looking for?

103. What is the most expensive hobby on your bucket list?

104. What is your favorite book?

105. What breaks your heart?

106. What is your zodiac sign?

107. What is your personality type?

108. Do you love pets?

109. Tell me something about your best friend?

110. What did your very first kiss feel like?

111. What is your favorite food to prepare?

112. What goals are you working on right now?

113. Who is your role model right now?

114. Do you believe soulmates exist?

115. What makes your first date a perfect one?

116. What is the one thing people don’t know about you?

117. Is there love at first sight?

118. What is your favorite drink?

119. How would you describe your former girlfriend?

120. Have you been in a serious relationship before?

121. Do you believe in true love/unconditional love?

Love and Relationship Questions

122. What expectations do you have of your girlfriend?

123. What is your most memorable birthday?

124. What is your worst ever prank?

125. What makes you insecure sometimes?

126. What is the one thing you cannot tolerate from a girlfriend?

127. What do you expect in a romantic relationship?

128. What do you remember of your teenage crush?

129. Have you ever pulled an April Fools Day prank on someone?

130. What is the most recent item you marked on your bucket list?

131. What is the meanest thing someone has ever said about you?

132. Do you have any questions for me?

133. Do you sometimes lie to get what you want from girls?

134. What is the most common lie men tell girls?

135. How do men ask for seggs without asking for it?

136. Do I make you nervous sometimes?

137. What is the one thing you like about me?

138. What is the one thing you don’t like about girls these days?

139. How should women appreciate men for their love and affection?

140. What do you do if you fall out of love with your girlfriend?

141. Can you give me a message if I asked?

142. Would you do anything if I asked you to?

143. Is it possible for a relationship to thrive without seggs?

144. What is the one thing that kills love?

145. Do you mind if I post a picture of us on Instagram?

146. What makes you jealous?

147. What makes you sure that you are ready to date?

148. If I asked to introduce you to my family, will you be okay with that?

149. Does anyone in your family know about us?

150. Why didn’t your last relationship work out?

151. How satisfied are you with our relationship?

152. Do you still find me as attractive as during the first days?

153. At what point did you feel like giving up on us?

154. Did you imagine we would come this far in our love life?

155. Do you sometimes feel like taking a break from the relationship?

156. If I were to go away for a year, would you remain faithful?

157. Is it okay for a guy to have lady friends?

158. Is it okay for a lady to have guy friends?

159. How many kids do you want?

160. What is the one thing you like about me?

161. If I were to change one thing about myself, what should it be?

162. What is the one sin you won’t forgive?

163. What would you do if we are to have twins as our firstborns?

164. Do you believe in gender roles?

165. What are your views on feminism?

166. Would you accept my financial help at one point in life if the going gets hard?

167. What do you think is the biggest threat to relationships these days?

168. Would you take care of me if I fell sick?

169. What is the one thing no one should do to someone they love?

170. At what point does love mature?

171. Is it okay to be protective of someone you love?

172. Who is poor at budgeting between us?

173. How will you feel if my income and net worth rises above yours?

174. Do you mind a large family?

175. Is it okay to be overprotective of someone you love?

176. What is the nicest thing a lady has ever done for you?

177. What is your earliest childhood memory?

178. What pisses you off easily?

179. What do you do when mad at someone?

180. What do you like about your life at this point?

181. What do you hate about your life right now?

182. What do you like about where you live today?

183. What do you hate about where you live right now?

184. Do you prefer a physical gift or a money gift?

185. Have you ever experienced betrayal?

186. What is your favorite thing about your friends?

187. How did you meet your best friends?

188. What makes you want kids?

189. What is the last illegal thing you did?

190. Have you ever peeped into someone naked?

191. When is the last time you had a healthy relationship?

192. How comfortable are you talking about your feelings?

193. What gives meaning to life?

194. What is the one thing you find yourself lying about?

195. What is the most unusual thing that turns you on?

196. How do you define a good relationship?

197. What would you like to do to me tonight?

198. When is the last time you used a dating app?

199. What is the worst date you have ever been on?

200. Do you enjoy dating?

Personal Questions to Ask a Guy

— Get to know him deeper

201. Why did your last relationship end?

202. How did your last relationship end?

203. How was your experience with your last partner?

204. Are you religious?

205. Are you spiritual?

206. Are you political? What are your political views?

207. Have you been in love before?

208. What is the one question you wish people should ask on a date?

209. Should people ask personal questions on the first date?

210. Have you ever been in a fight?

211. What was your last big fight all about?

212. Which ideologies are you strongly affiliated to?

213. Do you have a phobia?

214. Have you ever lost someone close to your heart?

215. What is your favorite movie as a child?

216. Would you rather play truth or dare?

217. If you were to die today, what will be your last wish?

218. When was the first time you got intimate with someone?

219. Have you ever felt attracted to another guy?

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

221. How about we skinny dip together?

222. How big are you for me?

223. How warm am I?

224. Are you the kissing with tongue type?

225. Can you remove my bra with your mouth?

— Random funny questions to ask a guy over text over text

226. What is your favorite photo of me?

227. Can I shave your privates next time?

228. Am I small enough for you?

229. When is the last time she had painful thighs after seeing you?

230. How do I smell down there?

231. Can I come with a lady friend next time we make out?

232. My bed is broken, can I sleep in your for tonight?

233. Can I wear your clothes for a night out?

234. Can I stroke your member?

235. Can I stick a finger in your behind?

236. What are your views on dating apps?

237. What is the one thing you have never told anyone?

238. Can you tell a lie to protect your relationship?

239. Do women lie more than men?

240. Do men cheat more than women?

241. How do men turn down sexual advances?

242. Can you love two girls equally at the same time?

243. Who loves more between men and women?

244. Would you cook for me if I asked?

245. What is the most romantic thing a lady can do for you?

246. What is the one gift you wish to receive?

247. When is the last time you got hard looking at a beautiful lady?

248. Have you ever m#sterbated looking at a photo of a celebrity?

249. Do you cuddle after smashing?

250. Would you check how wet I am right now if I asked you to?

There you have our complete list of weird funny questions to ask a guy to make him laugh.

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