300+ Superb Questions to Ask a Guy to Get to Know Him

You have no idea how good questions to ask a guy can change the way you communicate with each other and bring you closer together. However, it is important to not only know what questions to ask, but also to ask them right. The best way to do it is to use these questions to ask a guy when you both feel like having a dialogue. Some good scenarios are ones when the two of you are walking in a park, or sitting in a natural environment, a café or some other quiet place where no one bothers you.

An environment like this invites to a dialogue making the list of 300 questions to ask a guy incredibly effective.

Remember that there doesn’t have to be any particular order in the questions to ask a guy. Write down and memorize the questions that you personally like. You can also develop your own sequence of questions to a guy.

To make it easier to navigate through the article, the 300 questions to ask a guy are split into categories.

50 Best Questions to Ask a Guy That Help Start a Conversation

If you know what happened in a guy’s life today, you may start by asking about one of those things. For example, if a guy went to the movies today, ask him what movie it was, whether he liked it, etc., and then gradually move on to the list of 300 questions to ask a guy.

1. Do you have a best friend? How long have you been friends and how did you meet?

2. Are you an only child or do you have brothers or sisters?

3. Do you have any pets?

4. Did you have any funny moments in your childhood? Can you share a couple of the stories with me?

5. Have you been the same person as a child? If not, how have you changed?

6. Do you have a dream?

7. Do you set life goals for yourself? What is your life goal for now? What goals have you already reached?

8. How do you see your life in 5-7 years? What do you think will change?

9. Do you like active leisure? When and where was you last vacation?

10. Do you have a hobby? Is there something you like to do the most, something that brings you immense pleasure, and that you can do non-stop?

11. What book, film or TV series would you recommend me the most? And what of the above do you prefer yourself?

12. Do you like sports? What sport do you do now, or did you do in the past?

13. What things do you value in people? What traits do you like and dislike?

14. What was the happiest day of your life? Do you often think of it?

15. In what sphere would you like to be a professional?

16. What countries do you dream of visiting?

17. What is your dream job?

18. What do you expect to happen this year?

19. What skills would you like to develop in yourself? Do you think you have some hidden talents?

20. What did you want to become as a child?

21. What members of your family are you grateful to for the achievements in your life? Who played an important role in your life?

22. Do you often treat yourself? What was the last thing you treated yourself to?

23. What is your favorite holiday that you still like to celebrate?

24. What was your most memorable birthday present?

25. Did you have any unforgettable adventures in your life?

26. What is your Zodiac sign?

27. What inspires you to do big things?

28. Can you imagine your life without music? Who are your favorite performers?

29. Who is your closest person?

30. Are you sure that you really like what you do?

31. Where do you like to walk?

32. What events in your life made you stronger and wiser?

33. What does your ideal day look like?

34. What is the biggest achievement in your life?

35. Do you try to develop good habits? Like getting up early and doing morning exercises? Do you work on your self-development?

36. What are three positive qualities that you like about yourself the most?

37. Who do you like to spend your time with the most?

38. What is your favorite phrase or saying?

39. How do you like to spend time with your friends?

40. What would you change or improve in yourself?

41. Are you mostly a realist, an optimist or a pessimist?

42. What do you think is more important — family or freedom?

43. How do you help your parents?

44. What should everyone do in their life?

45. What holidays gather all of your family? How do you usually celebrate your birthday and New Year?

46. Do you keep your promises?

47. Do you think you would change if you became famous? If so, how would you change?

48. Do you like to be in the spotlight or behind the scenes?

49. What was the most difficult decision you had to make?

50. Are you a leader by nature or do you feel uncomfortable in a large group of people?

100 Interesting Questions to Ask a Guy to Get to Know Him Better

Below is the list of 100 good and interesting questions to ask a guy that will make your communication more interesting. Choose the questions you like the most, test them on your female friends, and then ask them to the guy.

51. Do you like sweets? And chocolate? What chocolate do you like?

52. Are you a beach or mountain person?

53. What is your favorite clothing style?

54. What do you think of tattoos and piercings? Would you get a tattoo or a piercing?

55. Did you have many toys when you were a child?

56. What is your favorite sleeping position? How early do you wake up?

57. What do you prefer to have for breakfast?

58. What are your good and bad habits?

59. What is your favorite dish?

60. If you had a million dollars, how would you spend it?

61. What movie character would you like to play?

62. If you were a superhero, who would you be?

63. What computer games do you like to play?

64. How often do you dream?

65. How do you deal with rude people?

66. Did you keep secrets from your parents? What were they?

67. At what time of the day do you feel most active?

68. Do you like to compete with stronger or weaker rivals?

69. Have you ever performed in front of a large audience? What event was that?

70. What are the things you cannot imagine your morning without?

71. If you wrote a book about your life, what title would you give to it?

72. Did you collect anything as a child? Do you collect anything now?

73. If you were a lead singer in a famous band and dedicated a song to your girlfriend, what would be the name of the song? What would the song be about?

74. What is the longest and shortest book you have ever read?

75. Have you ever been to a midnight movie?

76. Who in your family gave you your name? What does it mean?

77. How do you like to start your day?

78. What do you think of most often?

79. Is there something you have wanted to start doing for a long while, but haven’t got around to yet? Why?

80. Do you finish what you started?

81. What do you value the most in a friendship between a man and a woman and that between two men?

82. Do you sometimes want to be alone? How often do you go for a walk alone?

83. Were there any movies or TV series that reached deep into your soul? What were they?

84. What are the most annoying and admirable personality traits to you?

85. What kind of people do you find easy and hard to get along with?

86. Do you enjoy shopping for clothes?

87. What kind of music would make you dance right now?

88. Have you ever spent money on things you did not really need? Did you regret it afterwards?

89. Do you regret anything in your life that did not go as you wanted it to?

90. Do you follow the latest fashion trends? Or is it more a matter of your personal preferences in clothing?

91. Do you find sense of humor an important quality in the person you are talking to?

92. Can you stay serious for a long time?

93. How long can you hold a grudge against somebody?

94.Do you envy people who are more successful than you? Or are they more of an example to you?

95. How do you react to being criticized?

96. Can you read other people’s body language? What gestures can you read? What do they mean?

97. Do you like walking?

98. Have you ever cooked? If so, what was the first dish you cooked on your own?

99. What is your favorite season and why?

100. Do you like nightclubs and discos?

101. Do you have any fears? Do you think you can conquer them and how?

102. What would you like to do but have a fear of doing?

103. How should one spend a weekend to feel refreshed for the whole week?

104. How often do you make your own decisions to do something?

105. Have you been in situations when you put money in your pocket, forgot about it and then found it later? Were you glad to find it?

106. How many hours of sleep do you need?

107. What songs get stuck in your head?

108. Would you like to meet your doppelganger? How would you react to that?

109. Did you fight with other boys as a kid or were you a calm child?

110. What was the last concert or festival you attended?

111. Imagine that you are a famous singer — in the genre that you like. Who of the current famous bands or singers would you make a joint album with? How many songs would you write together and what would the songs be about?

112. We all had childhood dreams that we could not realize because there was no possibility to do so or simply because our parents would not let us to. Now that you are grown-up, have you realized any of your childhood dreams? And which of them would you consider realizing?

113. If you were a famous YouTube blogger, what would your videos be about?

114. If you were dating a girl, would you post pictures of you together on social networks? Do you think it is a right thing to do?

115. Do you often feel possessed with some new ideas? Do you write them down somewhere?

116. Is it easy for you to interact with new people?

117. What foreign languages would you consider learning?

118. Do you agree that foreign languages help you to think in a different way?

119. Do you often argue with people? Or are you more of a diplomat?

120. How did you earn your first money? How old were you then?

121. If someone mistreated you, can you give that person another chance?

122. Do you like to be a leader in a group?

123. Which football position would you choose for yourself — a striker, a defender, a halfback or a goalkeeper?

124. Did you participate in school competitions? What awards did you win?

125. Do you like to win? What do you think of failures?

126. Do you like to solve crosswords and puzzles?

127. When you make a mistake, do you blame them on yourself or other people?

128. Are you better at singing or dancing?

129. What pet name do your parents or best friends call you?

130. What are the most memorable compliments you have ever received?

131. Do you like to meet new people? What do you like about it?

132. What does your name mean?

133. Do you try to make a good impression on someone you like?

134. What should one do first — read a book and then watch a movie based on it or vice versa?

135. How do you know when a relationship is doomed to fail?

136. Should there be some mystery about a man? What kind of mystery?

137. What do you think of girls who take the initiative in relationships?

138. What does an ideal girl look like?

139. What is your idea of “heaven on earth”?

140. When an idea strikes you, do you start realizing it right away or do you need time to ponder over it?

141. They say there are no good and bad people, there are happy and unhappy ones. Do you agree?

142. Do you admire intelligent girls or are you afraid of them?

143. What would make your life happier?

144. People say: “Live every day as if it was your last.” What does it mean to you?

145. Do you tend to ponder over life? What have you been thinking of lately?

146. What gets in the way of developing a relationship between a man and a woman the most?

147. Do you have a female pen-pal whom you have never met, but who understands you like no one else?

148. Have you ever lived with a girl? If so, what are the upsides and downsides to it?

149. What do you think of girls who are very attached to their parents?

150. Who is more interesting to spend time with — people who are younger or older than you?

50 Deep Questions to Ask a Guy That Will Get Him Thinking

If you prefer more serious subjects that require a lot of thinking over, these 50 deep questions to ask a guy will open new horizons in getting to know each other for the two of you.

151. How would you feel about a girl who earns more money than you do?

152. Do you often talk to yourself asking yourself questions and giving answers?

153. Have you been in situations when you were so absorbed in your thoughts that you missed the place you were going to and walked another 300 meters?

154. Name three things you would take to a deserted island.

155. If you turned into a girl for one day, what would you do?

156. Have you ever witnessed a paranormal event?

157. If you could travel in time, where would you go?

158. If you could turn into any animal, what would it be?

159. Do you believe that our life is predetermined, and your every step and action, even our meeting, is not accidental?

160. Would you rather be famous when you are dead but non-famous while alive, or famous when alive but forgotten when dead?

161. Have you met people who pretended to be your friends and lied to you? How did you expose them?

162. Do you believe that everything you do, good or evil, will come back to you?

163. If you met a person of an opposite sex who shared your interests and thoughts, would it be an interesting or a boring experience?

164. Have you had dreams that were hard to discern from reality? What were they about?

165. Have you ever been woken up in the middle of a wonderful dream and wanted to go back to sleep and see it again?

166. Do you think you have super powers that other people on the planet do not have? Like maybe you could predict some events in your life by interpreting your dreams or otherwise?

167. Have you ever saved someone’s life? Like when somebody was drowning or choking on something? What were you feeling at that moment?

168. If you knew exactly when you would die, do you think it would change the course of events in your life? Would it make you a different person?

169. What do you do to refresh yourself when you feel worn out?

170. Have you been told that you look like someone you have never met in person?

171. If all jobs had the same working hours and were paid the same, what would you do for a living?

172. When you are in need, do you ask someone for help or try to solve the problem by yourself?

173. Do you think of what to say before you call someone?

174. If you could live to 90, and keep your 30-year-old state of either mind or body for the following 60 years, which one would you choose?

175. If you could change something in the way you were raised, what would it be?

176. If you could wake up tomorrow and have any quality or ability, what would it be?

177. How is love related to attachment? Or are these different notions?

178. Could tell a brief 4-minute story about me? What associations do you have with me? Based on what you know about me, what is your perception of my life, of what kind of person I am, of what I think? What do you and I have in common?

179. Are you more attracted to people who have the same traits that you do or those with opposing ones?

180. Do you hide your negative traits from new people? Are there people who know about them more than others?

181. In what order would you rank the following notions: money, family, career, creative activities, status, influence in society, friends, colleagues? Describe the importance of every notion to you.

182. If you could give yourself advice 5-10 years ago, what would it be?

183. What is the primary reason you cannot fall asleep?

184. Have you ever had prophetic dreams? What were they?

185. Do you believe in zodiac signs compatibility and horoscopes?

186. Have you ever lied to people in order not to offend them? What were those occasions?

187. Are you afraid of death?

188. Would you sacrifice your life for someone else? If so, who might it be?

189. How would you like to spend the last day of your life?

190. Whose opinion is more important to you — your loved ones’ or that of other people?

191. How has your past changed you? What events in your life have caused the changes?

192. Do you believe in life after death?

193. What can people learn from their mistakes?

194. Is there a way out of every situation?

195. If your child commits a crime, will you report him to the police?

196. Will you tell your friend that his girlfriend flirted with you?

197. If there were 25 hours in a day, how would you spend the extra hour?

198. How do you behave when among new people? Do you try to find a common ground with them or do you keep your distance trying to figure out if these people are your type and only then start a conversation?

199. Imagine that you are an interviewer. Who would you invite for an interview? Why? What 5-10 important questions would you ask this person?

200. Would you rather celebrate New Year in a group of girls with you being the only guy, or in a group of boys only? Why?

50 Personal Questions to Ask a Guy You Like

You like a guy, but you are not sure if he likes you back? Here are 50 personal questions to ask a guy you like that will help you find it out. Just take care not to ask all of the questions right away. If you do not know each other enough, he may become suspicious. To not draw too much attention and sound casual, ask the questions in between other parts of your dialogue.

201. If you like a girl, what do you do to win her?

202. What kind of girls do you like?

203. What kind of girl would you choose — one with a tough or soft personality?

204. Do you like bossy or timid girls?

205. What is important to you in a relationship with a girl?

206. Who should be the leader in the family? What do you think about a girl dominating in a relationship?

207. Are you a jealous person? How does it show?

208. How old were you when you had your first kiss? Do you remember the name of the girl?

209. What do you like best about me?

210. Do you like romantic dates?

211. When was the last time you surprised someone?

212. Where do you prefer to meet girls — in the street, on social networks or dating sites?

213. What do you feel inside when you know somebody likes you?

214. Do you like women’s perfume? If so, which ones do you like?

215. What do you think of infidelity in a relationship? Has anybody ever cheated on you? Have you ever cheated on somebody?

216. What is the formula of a happy relationship?

217. Do you like intimate talks somewhere by the water or under the starlight?

218. How should relationship problems be solved?

219. Do you like giving or receiving gifts?

220. Are you a spontaneous person?

221. Have you ever really loved anyone?

222. Do you believe in true love?

223. Have you ever kissed a girl you barely knew on a first date?

224. Do you think we could make a good couple?

225. Do you like me?

226. Do you think your parents will like me?

227. Will you introduce me to your friends? How would you introduce me?

228. Are you ready to live your whole life with one girl?

229. What do you think of planning something for the next weekend together?

230. Have you ever been approached by a girl in the street?

231. Is it important for you to have a personal space in a relationship?

232. Do you like to give flowers to women? When did you last give flowers to someone?

233. Do you like unexpected pleasant surprises?

234. Do you like natural or artificial beauty? What do you think of girls who wear eyelash extensions, fake nails, and dyed hair?

235. Would you like to start dating someone in the near future?

236. What traits should every girl possess?

237. What was the reason you broke up with your ex-girlfriend?

238. What would you not forgive someone you love?

239. Have you ever dated older women? What did it result in?

240. Have you ever checked the phone or social network account of your ex?

241. What does trust in a relationship mean to you?

242. Do you really care if your friends like your girlfriend?

243. Do you think that people who initially dated each other but it did not work out can be good friends later?

244. Is there such a thing as friendship between a man and a woman?

245. Have you ever dedicated your poems or songs to anyone?

246. Do you like my eyes and hair color?

247. Has a girl ever confessed her love to you first? How did you react to that?

248. If you could have dinner with absolutely anyone, who would it be?

249. In what way do you think we are alike and in what different?

250. How would you end the sentence: “I want to have someone to share…”?

50 Funny Questions to Ask a Guy and Make Him Laugh

These 50 funny questions to ask a guy will help divert you from more serious and profound subjects and just have a laugh together.

251. Do you often have to look for your socks scattered all over the place?

252. Could you run around a shopping mall in a women’s bathing suit?

253. Have you ever worn women’s clothes and high heels?

254. Have you ever worn women’s make-up? If not, would you like to try?

255. What funny nickname did your friends give you when you were a child?

256. What Christmas outfit did you have as a child?

257. Did your friends often play pranks on you in your childhood? What were those pranks?

258. Imagine that you are having a job interview and I am the person to conduct it. How would you behave?

259. What kind of humor do you like better: black humor or sarcasm?

260. Have you ever spied on a girl you liked?

261. Have you ever peeked into a women’s locker room?

262. Have you ever laughed in your sleep?

263. Have you been in a situation when you saw someone running and then falling down or falling off their bike, and you wanted to help but couldn’t help laughing?

264. What were the last funny videos you watched on YouTube?

265. What was the last movie mockery you saw?

266. Have you had any funny incidents with animals? Like when a deft monkey in a zoo ate your ice cream or when you were chased by an aggressive goat?

267. What was the funniest prank your friends played on you?

268. Have you ever been pushed into a pool in your clothes? If so, what were your feelings?

269. Did you draw on the walls at home with marker pens and pencils in your childhood?

270. Have you ever groomed your pets in some unusual way in your childhood?

271. Have you ever been on Chatroulette? Who was the funniest stranger you met there?

272. Have you ever run into a tree or a pole in the street because you were absorbed in your thoughts?

273. Have you been in a situation when you took something from a shelf in a shop and sent other items falling all over the place?

274. Have you ever tried pet food? If so, what did it taste like?

275. Can you do artificial respiration? Will you perform artificial respiration on me?

276. Can you give me three arguments for the existence of Santa Claus?

277. How can we save the planet from overpopulation?

278. What will you do if the Earth is attacked by aliens?

279. Which of the statements is more truthful: “Education is the only way to success” or “Fools are lucky”?

280. Imagine three girls named Jessica, Nicole, and Barbara. What flowers would you give to each of them?

281. Can you resist and not give a Like to a picture with cute cats?

282. Why is the sea blue while the water is transparent?

283. How long can you hold your breath? Let’s compete who can hold it longer!

284. Why do people need eyebrows?

285. Have you met girls who look like two different people with and without makeup?

286. Are you still a child inside? How does it show?

287. If girls had a pocket on their stomach like kangaroos do, what would they hide there?

288. Could you live happily with a girl who is a poor cook?

289. What would make you run away from a date?

290. If you could choose your gender before you were born, would you be a boy or a girl?

291. What makes you laugh until you cry?

292. If children’s toys came alive at night, what would they do?

293. If you had lipstick on your shirt, how would you explain it to your girlfriend?

294. If clothes on all people around suddenly disappeared, what would your reaction to that be?

295. Would you like to freeze your body for 100 years?

296. If your pet could talk, what would you talk about?

297. What words did you mispronounce in your childhood?

298. Did you hide your computer files from your parents? What kind of files were they?

299. Do you know someone whose laughter is a lot funnier than their jokes?

300. Have you made snow angels?

More Questions to Ask a Guy

If you liked the list of 300 questions to ask a guy and want to continue building the relationship, check out the following articles on the same subject:

  • 200 hardest would you rather questions to ask a guy
  • 500 best never have I ever questions to ask a guy
  • 500 truth or dare questions to ask a guy

Conclusions and Tips

The 300 questions to ask a guy will help build a conversation, understand your companion and receive some valuable information. If you have not had enough experience in asking guys questions or feel shy about putting some of them, you can practice doing this in front of the mirror:

  • Write out the questions to ask a guy you liked most on a piece of paper
  • Look yourself in the eye and start asking the questions minding your intonation
  • Ask yourself questions and answer them
  • Do this exercise for 15 minutes daily for a few days

As a result, you will not only learn how to properly use the list of the questions to ask a guy, but also how to answer the questions with certainty.

Do not ask too many questions in a row: this will look more like an interrogation than an interesting conversation. While asking a question, do not forget to look the guy in the eye and show your interest and desire to learn new things about him. Do not interrupt the guy while he is answering your question. Let him give a complete answer and then ask additional directive questions.

You can turn the process into a “Questions and Answers” game. The basic rule here is to answer the questions honestly and candidly — in this case, you will both enjoy yourselves. The game runs as follows: each of you answers the same question in turn. This will help you learn more about the guy while he will learn more about you.

Also, you will not need all of the questions to ask a guy for a first dialogue: 30 to 50 questions are quite enough, providing the guy gives full answers and you (as the interested party) ask directive questions and answer the guy’s questions.

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