205 Interesting Questions to Ask a Guy: Get to Know Him Better

Asking questions is an excellent way to spark conversations and get to know someone better. 

Whether you’re getting to know a new crush or deepening your connection with a longtime partner, asking the right questions can lead to meaningful and engaging conversations.

 In this article, we’ve compiled a list of 205 Random & Interesting Questions to Ask a Guy specifically tailored for guys.

155 Engaging Questions to Get to Know Someone Deeply

50 Romantic Questions to Ask Your Boyfriend for a Deeper Connection

 From random and fun inquiries to deeper and more i*ntimate discussions, these questions will help you learn more about him while having a great time.

Questions to Ask a Guy

1. What’s your favorite thing to do in your free time?

2. If you could travel anywhere in the world, where would you go?

3. What’s your biggest passion or hobby?

4. What’s your favorite movie or TV show?

5. Do you have any pets? If so, what are their names?

6. What’s the most adventurous thing you’ve ever done?

7. What’s your idea of a perfect day?

8. What’s your favorite book or author?

9. What’s your dream job or career?

10. What’s one thing on your bucket list that you haven’t done yet?

11. What’s your favorite type of music or favorite band?

12. Do you have any hidden talents?

13. What’s the best piece of advice you’ve ever received?

14. What’s your favorite food or cuisine?

15. What’s something you’ve always wanted to learn or try?

16. What’s your fondest childhood memory?

17. What’s your biggest goal in life right now?

18. What’s one thing that always makes you laugh?

19. What’s your favorite way to relax or unwind after a long day?

20. If you could have dinner with any three people, living or dead, who would they be?

Random Questions to Ask a Guy

Kickstart the conversation with these random questions that are sure to lead to interesting discussions and surprising revelations.

21. If you could have any superpower, what would it be and why?

22. What’s the most interesting thing you’ve ever learned recently?

23. If you could instantly become an expert in any subject, what would it be?

24. What’s your favorite childhood memory involving your family?

25. If you could live in any fictional universe, which one would you choose?

26. What’s the weirdest food combination you’ve ever tried that surprisingly tasted good?

27. If you could time travel, would you go to the past or the future, and why?

28. What’s your favorite way to relax and unwind after a long day?

29. If you could switch lives with someone for a day, who would it be and why?

30. What’s the most spontaneous thing you’ve ever done?

31. If you could have dinner with any historical figure, who would it be and why?

32. What’s the most adventurous thing you’ve ever done, and would you do it again?

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

34. What’s the best piece of advice you’ve ever received?

35. If you could have any job in the world, what would it be?

36. What’s your favorite thing about yourself?

37. If you could eliminate one thing from your daily routine, what would it be?

38. What’s something on your bucket list that you’re determined to accomplish?

39. If you could meet any fictional character in real life, who would it be and why?

40. What’s the most memorable dream you’ve ever had?

41. If you could own any exotic pet, what would it be?

42. What’s the most embarrassing thing that’s ever happened to you?

43. If you could instantly become fluent in any language, which one would you choose?

44. What’s your favorite season and why?

45. If you could live anywhere in the world, where would it be?

Interesting Questions to Ask a Guy

Dive deeper into his thoughts and experiences with these thought-provoking questions that will keep the conversation flowing.

46. If you could have dinner with any historical figure, who would it be and why?

47. What’s the most memorable dream you’ve ever had?

48. If you could switch lives with someone for a day, who would it be and why?

49. What’s your favorite conspiracy theory, and do you believe in it?

50. If you could live in any time period other than the present, when would it be?

51. What’s the weirdest food combination you’ve ever tried that surprisingly tasted good?

52. If you could have any job in the world, what would it be?

53. What’s your favorite unsolved mystery?

54. If you could be fluent in any language instantly, which one would you choose?

55. What’s your biggest fear, and have you ever faced it?

56. If you could travel anywhere in the world right now, where would you go?

57. What’s the most interesting fact you know that most people don’t?

58. If you could have any talent or skill, what would it be?

59. What’s the most adventurous thing you’ve ever done?

60. If you could have any superpower, what would it be and why?

61. What’s the most profound lesson you’ve learned from a difficult experience?

62. If you could relive one day of your life, which day would it be and why?

63. What’s the most beautiful place you’ve ever been to?

64. If you could know the answer to any question, what would you ask?

65. What’s your favorite book/movie/TV show, and why?

66. If you could eliminate one thing from your daily routine, what would it be?

67. What’s your go-to method for relaxation or stress relief?

68. If you could have a conversation with your future self, what would you ask?

69. What’s the most interesting hobby or interest you have?

70. If you could have any animal as a pet, mythical or real, what would it be?

Questions to Ask a Guy to Get to Know Him

Forge a stronger connection by asking these insightful questions designed to foster meaningful and heartfelt conversations.

71. What’s your favorite childhood memory?

72. What’s one thing that always makes you laugh?

73. If you could have any job in the world, what would it be?

74. What’s your biggest passion or hobby?

75. What’s the best piece of advice you’ve ever received?

76. If you could travel anywhere in the world, where would you go?

77. What’s your favorite book or movie, and why?

78. What’s your idea of a perfect day?

79. What’s something you’ve always wanted to learn or try?

80. What’s your favorite way to relax or unwind after a long day?

81. What’s a hidden talent or skill you have?

82. What’s one thing on your bucket list that you’re determined to accomplish?

83. What’s your favorite type of music or favorite band?

84. What’s the most adventurous thing you’ve ever done?

85. What’s your biggest goal or aspiration in life?

86. What’s your favorite thing about yourself?

87. What’s something you’re passionate about that not many people know?

88. If you could have dinner with any three people, living or dead, who would they be?

89. What’s your favorite season, and why?

90. What’s one thing you want people to remember about you?

Good Questions to Ask a Guy

91. What are your long-term goals, and how do you plan to achieve them?

92. What motivates you to get out of bed every morning?

93. What’s the most important lesson you’ve learned in life so far?

94. What’s your favorite way to spend a day off?

95. If you could change one thing about the world, what would it be?

96. What do you value most in a friendship or relationship?

97. What’s your idea of a perfect date?

98. What’s a cause or issue that you’re passionate about?

99. How do you handle stress or difficult situations?

100. What’s a skill or talent you’ve always wanted to learn?

101. What’s the best piece of advice you’ve ever received, and who gave it to you?

102. What’s a book or movie that has had a profound impact on you?

103. What’s your favorite way to unwind after a busy day?

104. What’s a dream you’ve yet to accomplish, but hope to in the future?

105. What’s your favorite thing about yourself, and why?

106. If you could travel back in time, what era would you visit and why?

107. What’s something you wish more people knew or understood about you?

108. How do you define success, and do you think you’ve achieved it?

109. What’s your favorite memory from your childhood?

110. What’s one thing you want to accomplish before the end of this year?

Flirty Questions to Ask a Guy

111. What’s your idea of the perfect date?

112. If you could take me anywhere in the world, where would it be?

113. What’s the most attractive quality you look for in a partner?

114. If we were stranded on a desert island together, what three things would you want to have with us?

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

116. If you could kiss me anywhere right now, where would it be?

117. What’s your favorite way to be flirted with?

118. If you could change one thing about our current situation, what would it be?

119. What’s the s*exiest thing a person can do?

120. If we were in a movie together, what genre would it be?

121. What’s your biggest turn-on?

122. If you could ask me anything and I had to answer truthfully, what would you ask?

123. What’s the most adventurous thing you’ve ever done in the bedroom?

124. If we were playing 20 Questions, what’s the first question you’d ask me?

125. What’s your idea of the perfect kiss?

126. If we could only communicate using emojis for the rest of the day, what emojis would you send me?

127. What’s your favorite thing to do to relax after a long day?

128. If we were at a party together, would you rather dance with me or talk with me in a quiet corner?

129. What’s the hottest fantasy you’ve ever had?

130. If we were in a crowded room right now, how would you let me know you’re thinking about me?

131. What’s your favorite part of my body?

132. If we were to go on a spontaneous adventure together, where would we go?

133. What’s the s*exiest thing you’ve ever worn?

134. If you could be any fictional character for a day, who would you choose and why?

135. If you could read my mind right now, what would you hope to find?

Add a playful and flirty touch to your conversation with these fun questions that are sure to bring a smile to his face.

Dirty Questions to Ask a Guy

136. What’s your biggest turn-on?

137. What’s your favorite position?

138. Have you ever fantasized about me?

139. What’s the d*irtiest dream you’ve ever had?

140. Where’s the craziest place you’ve ever had s*ex?

141. What’s your favorite part of my body?

142. Have you ever tried any k*inky activities in the bedroom?

143. What’s the naughtiest thing you’ve ever done?

144. Do you prefer to be dominant or submissive in bed?

145. What’s your favorite thing for me to do to you in bed?

146. Have you ever used any s*ex toys?

147. What’s your favorite type of lin*gerie?

148. What’s your biggest se*xual fantasy?

149. What’s the longest you’ve ever lasted in bed?

150. Have you ever had a one-night stand?

151. What’s your favorite kind of foreplay?

152. Do you enjoy watching a*dult films?

153. What’s the dirtiest text you’ve ever sent or received?

154. Have you ever had a threesome?

155. What’s your favorite way to te*ase me?

156. Do you enjoy dirty talk during se*x?

157. What’s the most adventurous thing you’ve ever done in the bedroom?

158. Have you ever experimented with role-playing?

159. What’s your favorite part about having se*x with me?

160. Would you ever try anything new or taboo in the bedroom if I asked?

Funny Questions to Ask a Guy

161. If animals could talk, which one do you think would be the rudest?

162. What’s the funniest joke you know by heart?

163. If you could switch lives with an animal for a day, which one would it be and why?

164. What’s the weirdest thing you’ve ever eaten and actually enjoyed?

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

166. What’s the most embarrassing thing you’ve ever done in public?

167. If you were a superhero, what would your superpower be and what would your costume look like?

168. If you could only listen to one song for the rest of your life, what would it be?

169. What’s the silliest thing you believed as a child?

170. If you could be any fictional character, who would you be and why?

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

172. If you could only watch one genre of movies for the rest of your life, what would it be?

173. What’s the most ridiculous rumor you’ve ever heard about yourself?

174. If you were a vegetable, which one would you be and why?

175. What’s the most embarrassing thing that’s ever happened to you on a date?

176. If you could only use one emoji for the rest of your life, which one would it be?

177. What’s the funniest movie you’ve ever seen?

178. If you could be invisible for a day, what would you do?

179. What’s the weirdest talent you have?

180. If you could create your own holiday, what would it be called and how would we celebrate it?

181. What’s the most useless talent you have?

182. If you could have any animal as a pet, mythical or real, what would it be?

183. What’s the weirdest thing you’ve ever seen someone do in public?

184. If you could only wear one color for the rest of your life, what would it be?

185. If you could live in any fictional universe, which one would it be and why?

20  Important Questions to Ask a Guy Before Dating

1. What are your long-term goals in life?

2. What do you value most in a relationship?

3. How do you handle conflicts or disagreements?

4. What are your views on commitment and m*onogamy?

5. How do you like to spend your free time?

6. What are your passions and interests?

7. Can you describe your family dynamics and relationships?

8. What role do you see communication playing in a relationship?

9. How do you handle stress or difficult situations?

10. What are your expectations for the future of your career?

11. What are your views on finances and budgeting?

12. How important is spirituality or religion to you?

13. What qualities do you admire most in a partner?

14. Can you describe your past relationships and what you learned from them?

15. What are your boundaries when it comes to physical i*ntimacy?

16. How do you prioritize self-care and personal growth?

17. What role do friendships play in your life?

18. How do you envision balancing your personal life with your career?

19. What are your thoughts on starting a family someday?

20. How do you define love and what does it mean to you?

These questions can help you understand the guy’s values, beliefs, and compatibility with your own desires and goals in a relationship.

Take things up a notch with these daring and provocative questions designed to spice up your conversation.

Engaging in meaningful conversations is essential for building strong and lasting relationships.

 By asking the right questions, you can deepen your connection with a guy and create memorable moments together. 

So, don’t be afraid to start the conversation and explore new topics together. Who knows what fascinating insights and experiences you’ll discover along the way?