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160 Interesting Questions to Ask a Guy You Like To Get To Know Him

A photo of Tom who is the Co-Founder of Questions About Everything

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Wondering what questions to ask a guy to get to know him? It can be hard to know what to ask the men in your life at times. That’s why we’ve compiled this post to give you a helping hand.

These interesting questions to ask a guy you like are a brilliant way to better understand the man in your life. We have talking points about what they’re looking for in a woman, their goals and their hobbies.

Ensure that you follow up on our good questions to ask guys by asking more questions. This way you can get into deeper conversations and find out what makes the boy in your life tick.

What we can guarantee with this list of good questions to ask boys is that you’ll have plenty of great conversations and get to know the man in your life better.

Questions To Ask A Guy List

  1. Can you imagine yourself as a househusband?
question to ask a guy on whether they could be a househusband

2. If you were dating a girl who earns more money than you, how that make you feel?

3. What do you think is the most attractive trait in a woman?

4. Would ever change career paths in the future?

5. Have you been with someone you knew was bad for you but stayed in the relationship anyway?

6. Did you ever get into serious trouble with your parents? What did you do?

7. Is there any topic you could talk about for hours?

8. Do you think you’re a positive or negative influence on those closest to you?

9. Do you have any female friends barring a girlfriend or wife?

10. Does it turn you on when women make the first move?

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11. What’s the funniest thing that happened while you were in high school?

12. If the girl you were dating made a drastic change to their appearance, how would that make you feel?

13. Would you rather go on a planned date or one that’s spontaneous?

14. Who’s the one person you’d choose to spend the rest of your life with if you had to choose now?

15. What three words would you use to describe yourself?

16. When did you have your first kiss? Who was it with?

17. How long do you wait before you sleep with a girl?

18. Are you a showoff in front of the girl you like or do you play it cool?

19. If you could evolve like a pokemon, what would you look like and what would you call yourself?

20. How far have you traveled to hook up with a girl?

21. How would you describe yourself on a dating profile?

question to ask a guy on how they would describe themselves on a dating profile

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22. How do you know when you love someone?

23. Is there any advice you wish you’d received when you were a teenager?

24. Is there a couple you’d like to emulate?

25. Have you been friends with benefits with anyone?

26. Should men and women have different roles in a relationship or should it be based on individual strengths and weaknesses?

27. Would you father your children like your Dad, or in a very different way?

28. What’s most important – wealth, power, or love?

29. What are your biggest goals for the future?

30. Do people trust you with their secrets? Should they or do you blab to everyone?

31. What attributes don’t you like about yourself?

32. Growing up, which fictional character did you find you identified with the most? Why?

33. Are you superstitious? If not, is there anything you have some level of superstition about such as double-checking something or not eating things past their best before date?

34. Are you thankful for what you have, or do you find yourself constantly wanting more?

35. What’s something people think about you that just isn’t true?

36. What’s the most important thing you need in your job? A solid paycheck? A sense of achievement? Good work colleagues?

37. Do you believe in God or some form of creator deity?

38. Have you ever done anything illegal? Why did you do it?

39. What’s your most embarrassing moment?

40. Are you an extrovert or an introvert? Do you think those labels are accurate or even helpful?

41. What’s your meaning in life? Do you think there is one overall meaning for everyone?

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42. What song gets you up and dancing at a wedding?

43. What thing is happening in the world right now that makes you most angry?

44. If you had a day to live, how would you spend that day?

45. What or who do you not appreciate in life as much as you probably should?

46. Do you have a plan for your life? What does it contain – career, family, or other life goals?

47. Will wealth inequality always be a thing? Is it necessary for a functioning society as higher paychecks can cause people to strive to be better at their jobs?

48. Who do you know that is not fulfilling their true potential? Do you think you are fulfilling yours?

49. If you could be the same age forever, but never mature mentally past that age, which age would you choose?

50. Where does morality come from? Is it just a human construct or something put in nature? If a construct, what right is it for us to impose it on others, if in nature, where did it come from?

51. What historical event would you have loved to live through?

52. What good thing are we losing in the 21st Century that past generations loved and appreciated?

53. Who has done the most to shape your beliefs about religion, society, and politics?

54. Have you ever been depressed? What was it like? Did you find others were supportive or dismissive?

55. If you were to become the leader of your country, what would be the first thing you’d fix?

56. What thing from the past could help us as a society right now, even if unpopular or seen as old-fashioned?

57. Do you think that machines will one day become more intelligent than human beings? Is there something to fear about that?

58. What most easily annoys you about someone else?

59. What thing we do now, will future generations look back on as barbaric or even evil?

60. What do you know is wrong but you struggle not to do even with that knowledge?

61. Why do people stay in bad relationships? Have you ever done that?

question to ask a guy on why people stay in bad relationships

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62. Do you think it’s good that modern medicine has meant that people live longer, or does it just mean that old people die in care homes now with dementia, instead of younger at home with their families?

63. Do you think the human race will ever colonize other planets or is it a stupid pipe dream?

64. Are there any problems with our current democratic systems that you can think of? How would you reform it?

65. Do you think humans will ever be able to be cloned? Would a clone of you be you, or someone new?

66. Is there a food, drink, or something else you put into your body, that you know is bad for you, but you do it anyway? Why do you do this?

67. What attributes do you like about yourself?

68. Would you call yourself religious or spiritual in any way?

69. What was the best year of your life? What made it so much better than all the others?

70. Have you ever cheated in any way? How do you feel about it now?

71. Is there anyone that you can tell, just by looking at them, what’s going on in their head?

72. What are you most proud of in your life?

73. What do you find most exhilarating?

74. What’s a mistake you keep making over and over again?

75. What action from the past would you do differently if you could re-live it again?

76. Do you think there’s more to us than just our base desires, or is everything we do just based on some primal need to survive?

77. How do you deceive yourself the most, or how do others deceive themselves?

78. What’s your greatest inner strength? Would others say the same thing?

79. What hobbies do you have? Any that you’re embarrassed about?

80. Which celebrity would you like to go on holiday with?

81. What’s the deepest thing in life that you’ve questioned?

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82. Is there something you have consciously deprived yourself of because you know it will benefit you in the future to do so?

83. If you could do any job in the world, what would it be?

84. Do you thrive on busyness or do you struggle under the weight of stress?

85. What death has most impacted you and those around you?

86. Do you believe in free will, or are we hardwired to make the decisions we make?

87. What were you really bothered by when you were a kid that seems ridiculous now?

88. When things are going well in life, do you just enjoy it or worry about when things will go wrong again?

89. What part of yourself do you hide from others?

90. What’s the biggest change you’ve seen someone go through?

91. Is anything unforgivable in your opinion?

92. What fictional character would you go on a date with?

93. If you were not allowed to work, what would you do with your time?

94. Do you listen more to reason or impulse?

95. Do you think pain is helpful? How has it benefited or ruined your life?

96. What action, in your mind, is a no-brainer that the government should be doing right now?

97. Do you read much? Is it something you wish you did more but find it hard to focus on when you do?

98. What are your greatest flaws?

99. Has anything ever happened in your life that you couldn’t explain rationally?

100. Do you ever wish you could be a child again? Why or why not?

101. Do you believe in life after death?

question to ask a guy on whether they believe in life after death

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102. What big thing would you change about your upbringing?

103. Have you ever had a brush with death? What happened? Was it actually exhilarating?

104. Are you addicted to something, even something socially acceptable? Have you ever been?

105. What habit would you love to stop, but have never been able to?

106. What most scares you about the future?

107. What’s your biggest regret and would you change it if you could?

108. What’s something you’re terrible at that everyone thinks you’re great at?

109. If you can’t sleep at night, what runs through your mind?

110. Is there someone’s life or some aspect of their life that you’d like to replicate in some way?

111. What did your parents pass on to you, that you’d like to pass on to your children?

112. What’s something you know you need to cut out of your life, but you just can’t seem to be able to?

113. What’s your greatest gaming accomplishment? A kill on CoD, 100 percent-ing a difficult game, or something else?

114. Do you listen to different music depending on what you’re doing?

115. What was the best meal you’ve ever eaten?

116. What would cause you to become vegetarian or vegan?

117. What’s your favorite food? What’s the food you like that others generally hate?

118. Is there a saying, poem, or verse that you remember at certain times of your life for a specific reason?

119. Do you have a movie or TV show you’ll always put on when you’re ill?

120. What terrible thing has happened to you that’s hilarious in hindsight?

121. What have you seen that you wish you could un-see?

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122. Do you find it easy to hide the fact that you don’t like someone and be polite to them anyway, or do you show it without meaning to?

123. Who or what made you laugh the most when you were a child?

124. What’s your biggest fear? Is it rational or irrational to be scared about it?

125. Do you think actors should lecture us on morality and social justice when they accept awards? Are their hearts genuinely in the right place or are they just trying to look good?

126. Do you find yourself guessing or worrying about what others are thinking about?

127. Do you know what your name means? Do you think names mean something deep about a person or are they just a name?

128. Do you think we ever crossed paths with one another before we actually met?

129. Would you prefer to live in a house in the country or a flat in the city?

130. Have you ever tried writing a novel or some kind of creative writing? Does that appeal to you? Are you creative in some other way?

131. What’s the worst thing you’ve ever done?

132. If you could choose one animal to anthropomorphize, as in giving them human intelligence and attributes, which would you choose and why?

133. Do you think fear is a good thing? In what ways does it hold you back? In what ways does it help you?

134. What do you find you’re judgemental about in others? Are you judgemental about yourself?

135. What’s something you started you hated but with persistence, you learned to love?

136. What memory haunts you to this very day? Why do you think it’s so prevalent in your mind even now?

137. What socially unacceptable thing do you secretly wish you could do?

138. When have you been the most down or even depressed? What got you through it?

139. Have you ever been through heartbreak? Have you ever put someone else through heartbreak?

140. What are some of your favorite activities to do on a date?

141. What celebrity tragedy makes you the saddest?

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142. Do you find it easy to focus or do you get distracted easily?

143. Do you think the best things in your life are gone or are they yet to come?

144. What was the greatest cinematic experience of your life?

145. What do you find most upsetting that is going on in the world right now?

146. What do you have to do every day that you hate doing?

147. Are you a morning bird or a night owl?

148. What’s the most comfortable bed you’ve ever slept in?

149. Have you ever made a decision that later you don’t understand your reasoning behind?

150. What movie do you love, but the more you watch it, the more you see the mistakes or plotholes?

151. Is there a colloquial phrase or saying that you say a lot?

152. What’s the oddest thing you’ve found in your bag, wallet, or pocket?

153. What makes you most happy?

154. How do you think society would cope if the internet was cut off?

155. What moment in your life has made you feel most alive?

156. What’s your favorite food that you love to snack on?

157. How much money do you think would be enough? If you had it, do you think it would then feel like it wasn’t enough?

158. What do you feel ‘they don’t make like they used to’?

159. What do men really think of women?

160. What’s your most memorable dream?

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A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.