Asking questions is one of the best ways to engage with and get to know a guy you like. But sometimes, it can be confusing to know exactly what to ask. 

“What if he finds I question offensive?” “What if I ask a dumb question?”

But here’s the thing: The trick is to keep the questions casual and open-ended. And more importantly, you don’t need to ask a lot of questions. Each question you ask him is probably going to provide endless topics to discuss. 

That said, here are 101 random fun questions you can ask a guy you like to get him talking. Remember, you don’t need to ask him all the questions on this list. Pay attention to his answers and build on what he says. Don’t interrogate him.  

1. What do you find most attractive in a girl? 

2. What do you do for fun?

3. What’s your worst day ever?

4. Do you think the guy should always pay for a first date? 

5. Who do you want to be like? 

6. If you had all the money you wanted, what would you do? 

7. Which town did you grow up in? 

8. How was your experience growing up? 

9. What’s your best day ever? 

10. Which celebrity do you admire the most? 

11. Would you like to be famous? 

12. Which movie can you never get tired of watching? 

13. Which female celebrity do you find most attractive? 

14. What’s your favorite book of all time? 

15. Have you ever had a life-changing experience? What was it like? 

16. What do you do to relax? 

17. What skill are you a natural at? 

18. What’s your favorite sport?

19. What’s your most cherished memory of your childhood? 

20. What did you want to be as a kid? 

21. What do you think about superhero movies? 

22. What do you wish people understood about you? 

23. What trait quickly catches your attention in a lady? 

24. Have you ever been in love? 

25. What’s your best accomplishment? 

26. What’s the most dangerous thing you’ve ever done? 

27. Do you consider yourself introverted or extraverted? 

28. What do you wish people knew about you? 

29. Do you have a best friend? 

30. Where would you like to be in the next five years? 

31. What’s your favorite TV show? 

32. What did you first notice when you saw me?

33. What’s your best food? 

34. Do you like pets? 

35. What’s your favorite pet? 

36. Do you think you would enjoy working under someone? Or would you prefer to build your own thing?

37. What were your previous relationships like?

38. What’s your dream job? 

39. Have you been in a serious relationship? 

40. What do you think about dating a coworker? 

41. What’s the best thing you do for pleasure? 

42. Which is most important to you? Looks or attitude? 

43. What do you think is the ideal age to get married?

44. If you could come to this world again, would you still like to be you? 

45. Do you consider yourself a trustworthy person? 

46. Would you prefer a casual or a serious relationship at this point in your life? 

47. Would you prefer to be self-employed or have a corporate job? 

48. What do you like the most about yourself? 

49. What big changes have you undergone in the past few years? 

50. Why did your last relationship end? 

51. What’s your favorite color? 

52. Are you dating anyone? 

53. What’s your favorite dish?

54. Do you like football? And what team do you support? 

55. What are your dos and don’ts? 

56. What kind of girl would you like to date? 

57. What position are you in your family? 

58. What turns you off in a woman? 

59. What calms you down when you’re angry? 

60. Who is your favorite person in the world? 

61. Can you cook?

62. Do you love watching movies? 

63. What’s your shoe size? 

64. What are your plans for the future? 

65. Can you date an older woman? 

66. How would you describe yourself in three words? 

67. Can you drive? 

68. What’s your favorite song? 

69. What’s the funniest thing you’ve ever done? 

70. What irritates you the most about people? 

71. What trait do you find most attractive in a woman? 

72. What’s your biggest fear in life? 

73. What’s your biggest regret? 

74. Can you tell me a secret about yourself? 

75. Are you proud of where you are right now in your life? 

76. What’s your favorite snack? 

77. How would you describe your family? 

78. What do you value most in life? 

79. What does an ideal life look like for you? 

80. What’s the craziest thing you’ve ever done? 

81. If you could relive your past, what would you change? 

82. Which school did you go to? 

83. What was your favorite subject? 

84. Where do you work? 

85. What did you want to be growing up?

86. What caused your break up with your ex?

87. Who do you like more, you mum or dad? 

88. What thing about you do you think people underestimate? 

89. What have you failed at? 

90. What are you most proud of about yourself? 

91. Did you enjoy school? 

92. Are you a religious person? 

93. Do you believe in God? 

94. Do you have a nickname? 

95. Do you have a pet? 

96. What cool things do you know how to do? 

97. Can you sing? 

98. Where did you grow up? 

99. What’s the best thing about being you?

100. What’s your best valentines day experience? 

101. What do you have passion for? 


The type of question you ask a guy will depend largely on the level of relationship you already have. If you’ve just met, then surface-level questions are the best to go. 

But if you’ve known each other for a while and you just want to deepen the bond and know him better, then you can go for the more personal stuff. 

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