250+ Really Interesting questions to ask a guy

When you meet the guy you like or enjoy spending time with, there’s one thing you need to also do, keep his attention.(Read also: 100 More Interesting Questions to Ask A Guy)

In most cases, it has always been men who try so hard to break the ice but what if your guy has had a long day or is not in the mood? As such, the article provides a list of really interesting questions to ask a guy to help in keeping the conversation going. The questions range from; really good questions to ask,romantic questions,funny,deep and dirty questions to ask a guy. Check them out and enjoy!

175 Random interesting questions to ask a guy

1. I cannot believe I have forgotten my mobile phone number, can I have yours then?
2. In case you were an actor in Hollywood. Which character do you think would fit you?
3. Can you spell the word antidisestablishmentarianism in one minute?
4. In case you were an actor, which role would you prefer to play between a villain and the good guy?
5. Which TV character do you think is the funniest in the whole world?
6. Which movie star do you think in the most villain character of all time?
7. What is the most evil thing have you ever thought about a person?
8. How often do you give tips to waiters for great service delivery?
9. How have you used your most important skill to improve your life?
10. Have you ever taken a bribe to cover something bad?
11. What is the most frequent thought that comes in your mind every morning?
12. Where is your original home and how many new places have you lived?
13. What is that thing you have wanted to do but you haven’t yet?
14. Are you the type of guy who takes “NO!” for an answer when approaching a lady?
15. Where do you wish to propose for you longtime girlfriend?
16. How many applications from girls have you received so far?
17. Would you date a girl from another race? What do you find attractive about them?
18. How many friends from another race do you have?
19. Is your friend of your race or he is from a different race?
20. What turns you off when dating a woman from a different race?
21. Would your parents support your affairs when you date a girl from a different race?
22. Would you miss your favorite and the most awaited game to spend time with your girlfriend?
23. Who among your friends hates your girlfriend so much? And why?
24. Who among my friends do you not like at all? Why?
25. If you could be a woman, how long could you have awaited to get married?
26. If you wake up one day and find yourself turned into a woman. What about your life do you think will change with immediate effect?
27. Are you a playboy?
28. How many girls are you seeing now?
29. What do you find interesting about dating many girls at the same time?
30. Can you marry a disabled girl?(who cannot walk)
31. Your face looks familiar, are you from….. (Name the place you think you once saw him)?
32. What is the latest I can call you in the evening?
33. Where did you meet your current girlfriend?
34. Have you ever supported xenophobic in your life?
35. What was the reason for dumping your girlfriend?
36. Do you regret for dumping your girlfriend?
37. Have you ever been dumped by a girl? What did you do or happened?
38. What are you most committed to in life?
39. Who have you ever made out with?
40. Do you prefer to date fat or slim ladies?
41. Do you prefer to date a girl older than you, age mates or younger than you?
42. Which category of women do you think is easy to approach; younger than you, age mates or older women?
43. Have you ever been embarrassed by a lady in public? What happened?
44. Who was your childhood girlfriend?
45. How many jobs have you quit so far this year?
46. What is the most exotic thing that you have ever purchased?
47. Are you planning to change your occupation?
48. Who do you think is the most handsome/cute movie star in the world?
49. Which among all the movies you have watched do you rate very low?
50. Which this year movie you think is the best?
51. Which movies are you waiting eagerly for the release?
52. What do you love about Disney world production movies?
53. Are you a fun of cartoon and animation movies?
54. Which genre of movies don’t you like?
55. What is the most expensive item you have ever broken accidentally?
56. Have you ever told someone, “You see, that is what I told”?
57. How many riddles can you tell me right now?
58. Have you ever gotten hiccups while taking a drink in an important meeting?
59. How do you feel when a girl you have always admired is kissed by another guy in your presence?
60. Imagine seeing your spouse being given a tight hug by a smartly dressed guy, would you take it easy?
61. What romantic movie quotes do you use when you meet your crush?
62. What picture or movie makes you laugh even if you look at it several times?
63. What game are you most addicted to on your smartphone?
64. Would you eat food that looks fine yet it is past its expiry date?
65. Would you accept to act like a baboon in the animal zoo for 5000 dollars per month?
66. Among your best friends who do think has no filter in their mouth and brain?
67. Which foreign language do you wish you could be in position to speak fluently?
68. Think of this scenario, you have a car with capacity to carry only one person, your wife and your mother gets stranded at night, between the two who would you leave behind?
69. If you were a crazy scientist, what experiment would you do involving women?
70. Among your family members, who do think is the luckiest person? Why?
71. Which private beach you have been to? How was it, beautiful?
72. What social trend among your friends are you tired of?
73. Have you ever pretended to know a lot about an issue but in real sense you have no idea?
74. Have you attended a wedding? What lessons did you learn from it?
75. How would our marriage be if we moved in together?
76. Where have you ever slept but felt so much uncomfortable?
77. Do you like singing? Which song do you only know its chorus?
78. If you wanted your roommate to go crazy, what kind of note would you leave for him on the table?
79. Have you ever felt embarrassed for mispronouncing simple words? What were they?
80. What is most expensive thing that you can buy for your girlfriend?
81. Do you think your name has contributed to who you are?
82. What profession would you never like to be?
83. Are you proud of being a man? or you would wish to be a woman?
84. Have you ever applied the slogan “fake it until you make it”?
85. If you were a grandparent today, what interesting stories would you tell your grandchildren?
86. How many hours do you spend sleeping?
87. When you meet your crush, do you always say the truth or you hide some things?
88. When you go to a restaurant, do you prefer to pay then eat or eat then pay?
89. What are your ambitions? How are you planning to fulfill them?
90. Where do you access daily news?
91. What is the best way of firing someone from work?
92. Do you still have the photo you took when you were a small kid? How did you look like, handsome?
93. If you were a celebrity, what things would you do to ensure that you always on the news highlights?
94. What would be the worst thing to see or hear when you are going for a heart surgery in theatre?
95. What one thing would you like to do to be included in the Guinness Book of Records?
96. Have you ever regretted for despising something your were warned before?
97. How would you like to be addressed when people are talking to you?
98. What designer jacket do you possess?
99. What is the worst thing that can end your relationship?
100. What social controversial issue do you feel deeply about?
101. How many are you in your family? How do you relate with your siblings?
102. What is the most challenging situation that you have gone through?
103. What is that thing that your spouse would like you to change? Are you ready to change?
104. What do you enjoy most with your girlfriend every time you meet?
105. What is your dream vacation? How are you planning to make it a success?
106. How did you handle you ever had with your girlfriend?
107. Can you think of your best fictional villain?
108. When do you feel happiest and most contented?
109. Between your friends and your family, who are in position to describe you more accurately?
110. What would be the things they would mention while talking about you?
111. What can you tell someone about your spouse?
112. What possible concerns do you think your wife can have about you?
113. What is the worst thing of being a man?
114. What thing would not do or do when give one million dollars
115. What type of food do you hate absolutely?
116. Have you ever received a serious injury? How did you get it?
117. Have people said you own too much of something? What is that?
118. Have you ever experienced a situation that made you sweat? How did you go about it?
119. Between school and college, what has impacted on your life the most?
120. What have you ever done to improve someone’s life?
121. What area would you wish to be an expert in?
122. What personal thing would you struggle to save when your house caught fire?
123. What good thing would you like at least everyone to experience in life?
124. Have you ever done an unusual thing? What was that?
125. Are you good at any game/ sport?
126. Do you like playing cardboard games?
127. Which one is your most preferred/least preferred cardboard game?
128. Have you ever felt extremely sorry for someone in a movie?
129. What thing could you do all day long without getting bored?
130. What have you learnt recently?
131. Have you ever lost something that was precious to you? Did you find it?
132. Have you ever received a complement that has always stuck in your mind?
133. What comes in your mind when you come a across a homeless man?
134. How is your best close friend?
135. Are you comfortable with all things happening in your life?
136. Whom would you like to accompany you to a foreign country?
137. Do you wish to live forever? Why/ why not?
138. What is your favorite means of transport? Why do you like it?
139. Do you think your parents raised you in a perfect way?
140. What did you miss when you were growing up?
141. Would you rather fix things yourself or ask for assistance?
142. Do you believe horoscopes really reflect your real life experiences?
143. Between casual and official attire, which one do you prefer?
144. What or who do you thank God most for having given you?
145. What habit is accepted socially but you feel uncomfortable with?
146. What do you find so strange about yourself?
147. Which celebrity would you wish to have as your president?
148. Which celebrity do you think would be a nuisance if he/she is the president of your country?
149. What (if any) makes you become so much afraid?
150. Which is the serious problem that is facing the world today you would like to solve given an opportunity?
151. Who is your oldest relative who is still alive? How old is he/she?
152. What is the most significant and unique tradition your family has?
153. What kind of people you cannot stay with for a day?
154. What wakes you up every morning?
155. If you were to design and built a house on your preferred tree, how would it look like?
156. What features would that house have?
157. Which movie would you wish life to be more like?
158. What are the three things you can never spend your money on?
159. Have you ever gotten stressed up over something but later turned out to be no big deal?
160. What current issues are you tired of hearing?
161. What is the most important thing that people get it wrongly?
162. Who has lost your trust and respect completely? What is the reason?
163. How would you like the government address the crime issue?
164. Between health and wealth, what do you pray for often?
165. What question do you ask someone when you want to know more about him/her?
166. What signs tell you that this person would be successful in future?
167. What have you always been doing wrong but you knew the perfect way of doing it recently?
168. Would you rather buy a great book or a great movie?
169. Would you rather ask for forgiveness or ask for permission?
170. Do you consider yourself a superstitious guy? What is it about?
171. Would you rather be in the shape of a hologram or two dimensional?
172. Have you ever received a prank call? Tell me the story.
173. What rules have set for yourself?
174. What is the strangest thing you have seen someone do in public?
175. What can you recommend to a person who is free and don’t know what to do?

Flirty and funny questions to ask a guy

Also Read: 1000 Interesting Questions to Ask People-Boy,Girl,Parents and more

1. How can you describe my body odor?
2. Do you think you are ugly or handsome?
3. Would you rather say all that you have in your mind or never to talk again?
4. If you were a waiter and your clients are complete jerks, how would you handle them?
5. If you were a disease, what would be your symptoms?
6. Would you have a cure?
7. Have you ever been caught by the police for peeing in public places?
8. What would you do if you found a briefcase with one million dollars inside? Would you keep it to yourself or you would take the cash to the police station to look for the owner?
9. Who do you think was the most funny childhood friend?
10. Who among your childhood friends always got you into trouble?
11. Whom among your childhood friends used to be very polite but now he is everywhere?
12. Which vocabulary do you think I normally use?(A day cannot pass without me using it while we are talking)
13. Have you ever been bitten by a lady thoroughly?
14. What genetic modification you would like to be done on you?
15. Have you ever deleted your own social media post? What was it about?
16. Do you think you can knock someone out of their senses by a single punch?
17. Have you ever been approached by a female teacher?
18. Which body part would you ensure it has been enhanced if you were to change your gender?
19. If we end up together in the future, whom would you wish our children to resemble?
20. Have you ever felt like you own me?
21. Do you think I owe you anything?
22. Assume I am a baby. How would you explain to me the difference between a bird and a bee?
23. Whom do you consider a jerk of all the girls you have met in life?
24. Do you feel comfortable farting loud while with your girlfriend?
25. What could you do if you notice I was starting to get a crush on you?
26. If you were to choose an African country to live for the rest of your life, which country would you prefer?
27. Have you ever been drunk till you passed out?
28. What memory about us is still fresh ever since we met?
29. What made you to stop cheating in exams in college?
30. Have you ever been slapped with your best friend? If yes, what had you done to him?
31. Which extreme adventure sport have you played in life?
32. Have you ever winked at yourself in a mirror?
33. What was the cheapest staff in your closet? How much did you bought it?
34. When did you last indulge in PDA? Whom did you want to make jealous?
35. Do you think I have a manipulative behavior which turns you off sometimes?
36. What would you do if you date a girl who is a terrible cook and lazy?
37. Which means of transport have you never used and you would wish to try before you die?
38. Is there a sexy scene in a movie that you would to do live with me?
39. Where would your eyes move faster to see if my dress falls off?
40. What shows that you are proud of your girlfriend?
41. How well can you explain how a plane operates?
42. What is the one thing you tell yourself in the mirror?
43. Have you ever asked your friend to give you pickup lines before approaching a girl?
44. Would you wish to spend a day with an alien?
45. What is the silliest thing you have done with your friends when you are on vacation?
46. If you were a girl, how would you prefer yours body shape to be like?
    

    

47. Can you watch a romantic movie with your parents in a sitting?
48. What are you best at while in bed?
49. If I ask you to send me a nice picture of your favorite body part, which part would that be?
50. Do you like when your girlfriend is much possessive over you?
51. What excites you, flirty skirt or tight jeans?
52. Who is a real man according to you?
53. If you were to marry one fictional character, which would that be?
54. What is the one thing you would like your spouse to do that she has not done?
55. Were you ever given “the bees and the birds” talk?
56. How would you react when you are watching a movie with your parents and a dirty scene appears?
57. What actions do you do to woo girls? Which one works best for you?
58. How many single girls have saved in your phone book?
59. Do you flirt with ladies that you have their phone numbers?
60. What kind of movies do you search for online?
61. Have you ever pretended to be a girl?
62. Would you like to also walk on heels?
63. If you were a girl would you ever leave your house without putting on makeup?
64. How many seconds or minutes can you take to reach there?
65. What animal resembles you in appearance?
66. What animal can you compare your personality with?
67. Which is your best animal sound? Would you do it for me?
68. Do you think you would ever drive a SmartCar?
69. When you look at yourself, do you think you can survive a zombie apocalypse?
70. Would you rather prefer intelligence or happiness?
71. Would you rather be a zombie or vampire? Why?
72. Would you rather be carried in a tanker or submarine?
73. How do you do it, wet the toothbrush before or after you have placed toothpaste?
74. Do you ever think of getting mad at me?
75. Would you rather not hear or not see?
76. Would you prefer to scream each time you sneezed or fart each time you yawn?
77. What would be the most interesting game if players were to get drunk before going to the field?
78. For how long can you hold your breath? Would you try it?
79. If you are given one hour with a stranger what things would you ask him or her?
80. Have you ever been attacked by a gang while you are with your girlfriend?
81. Do you look at me as a wife or a girlfriend?
82. What thing can you do with your girlfriend but not your wife?
83. What would you do if your ex- that you loved most brings you a gift during your wedding?
84. Do you like skinny dipping?
85. Do you think you immediate neighbor gets disturbed when you do it loud?
86. What would you do if your neighbor knocks at your door in a bikini?
87. Have you ever been attracted to your cousin?
88. When were you blindfolded last?

Also Read: 190+ Family Questions To Ask Your Parents, Siblings (Interesting and Funny)

Hope you’ve enjoyed our list of questions to ask a guy. Make sure to contribute to the topic by leaving your question(s) on the comment section below.

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