104 Interesting and Funny Questions to Ask a Guy

If you are a funny woman and want to surely stroke a guy’s ego while making him feel super excited and wanted, then just ask him confidently lots of questions. Then really listen to their answers carefully. You will certainly have the guy on a hanging string in a few seconds!

It is to keep in mind that the ego-stroking may happen with the act. But if you ask and really listen to there will be also a genuine side of the picture as well. Because the people who are actually interested in someone else and directly ask logical and great questions are the only people who are always popular, accepted and well liked by all. Showing faking interest is the worst thing you can do to others. And at the end of the day, you will not be a natural listener! If this is the scenario you decide for others, and then put yourself to that test and practice. You will start to discover more people and learn so much about so many things, truly, knowing people worth at the end of the day!

Interesting and Funny Questions to Ask a Guy

Here’s I have compiled 103 interesting and funny questions to ask a guy that you can ask to get your conversation rolling with a guy!

Personal Question to Ask A Girl

1. Among all who was your most beautiful girlfriend?

2. What persona in me pulls you towards me the most?

3. If you get an option, is there anything you would like to change about me?

4. Have you ever got slapped by your ex girlfriends or any other girl?

5. Do you hate anything about yourself?

Relationship Questions to Ask A Guy

6. Who is that one person you mostly and secretly hate in your family?

7. What’s your real thought of marriage?

8. Do you believe in marriage?

9. With which girl in your life do you want to get married?

10. Are you comfortable in a live-in relationship?

11. What were the first words you spoke at your very first date? What happened exactly? Where did you take her?

12. Do you love the girl with whom you dated last night?

13. What do you really hate about your best friend?

14. What was the worst date that you have been on?

15. Have you ever got a crush on your best friend’s girlfriend?

16. Have you ever cheated on someone before?

17. Have you cheated any of your girlfriends?

18. Do you shy away or scared of real love?

19. Are you going to marry your girlfriend?

Questions to Ask A Guy About Profession

20. Does your boss really like you or always does he take you as for granted?

21. How much money do you hope to make in life?

22. Are you ever jealous of me and my career?

23. Have you ever been jealous of your closest friends?

Spiritual Questions to Ask A Guy

24. If now you could go on a sudden dream holiday, where on earth would it be?

25. What is the wildest thing you have ever done so far?

26. If you were lucky enough to win the lottery, what would you do with the money?

27. If you were unluckily caught in a fire and had to decide between saving the life of your dog and new TV, which one would you choose?

28. Who do you talk to more when in a problem, your mother or father or girlfriend?

29. If suddenly you came across a genie who would offer to make three of your wishes instantly come true, what would those wishes be?

30. Do you have any addictions other than girls?

31. What are your fetishes?

32. What habit of yours makes you less desirable to the girls? What do you think?

33. Do you believe that ghosts and demons exist in the real world?

34. Do you believe in God and worship?

35. If you were stranded alone on a remote island, how could you get away?

36. Do you believe in the concept of life after death?

37. Do you pray?

38. Do you ever read a single page of the bible?

39. What super power do you dream of having? Or which super hero you desired to be in the early days?

40. Which famous person would you like to be?

41. Do you get scared of the dark?

42. Who or what do you look up to most in life?

General Questions To Ask A Guy

43. What is the one most embarrassing thing you have ever experienced?

44. Are you fond of children?

45. How many children you cherish to have?

46. What is the one single thing you want to change about yourself?

47. What is your biggest dream in life?

48. Describe the greatest and funniest adventure you have ever been on?

49. Name on expensive thing that you bought and now regret buying?

50. What would you buy for your wife as the first anniversary gift?

51. Have you ever sat before a girl and asked the girl to marry you?

52. If you had to choose between me and your closest friend, who must you pick?

53. What is the one thing that you are most ashamed of doing to a friend so far?

54. Would you go out of your way just to help a friend?

55. Have you ever asked the girl to pay for the date because you forgot your wallet at home?

56. What’s your favorite sports car? Name single car!

57. Do you lie very often?

58. Who is your favorite actress?

59. If you could go on a date with your favorite actress, where would you take her? What would you tell her on first eye contact?

60. Do you keep secrets?

61. What is your favorite childhood memory?

62. Would you ever go hunting for sport?

63. Are you interested about pets? What pet would you have if given a chance to keep one?

64. Which cartoon did you like the most in childhood?

65. In which class was you when you had your first crush?

66. Were you ever drunk at college?

67. At what age did you start smoking and drinking?

68. Have you ever tried to steal?

69. Do you believe that there is only one love for everyone?

Questions To Ask A Guy About Sexual Ideology

70. Have you ever kissed a guy?

71. Are you virgin?

72. Do you think you are perfectly happy with your life?

73. Do you still think about your first love when got upset?

74. Do you have any wild and sexy fantasies?

75. What’s the highest priority for you when considering your partner – good looks, hotness, intelligence, rich, personality, or something else?

76. What’s the difference between having sex and making love for you and which do you prefer?

77. If you could change the age at which you have lost your V (virginity), should you?

78. What’s your biggest sexual ‘turn-on’ and ‘turn-offs’ of your life?

79. Have you ever been caught touching yourself sexually? If you did so how old were you? Who caught you?

80. Do you like experimenting with new girls and things in life?

81. Do you think my friends are sexy and hot?

Weird and Funny Questions To Ask A Guy

82. Do you believe there are aliens outside world?

83. Have you ever cried in bathroom for being dumped by someone?

84. What was the wildest dare ever given to you by your friends? Could you chase the dare?

85. How old were you when you went on your first date?

86. Do you ever want to win a Nobel Prize of any sort?

87. Describe me in one word.

88. How would you represent me before your mother?

89. Would you ever consider putting your parents in an old age home?

90. Have you ever been arrested?

91. What was the strangest and peculiar punishment your parents ever gave you?

92. Do you like going for parties only to check out beautiful girls?

93. Are you Eco conscious?

94. Have you ever had a date with a person that is much fatter or slimmer than you? When you saw them for the first time what did you think?

95. If in an instant you could become an unseen man, what must you do at very first? Where must you go?

96. Have you been to a party and being the one asking all the questions and doing all the listening?

97. If you’re a waiter and a customer became extremely rude, what would you do? Would you drop food unintentionally on them or think about doing something like this?

98. What was your favorite cartoon character as a kid and why did you enjoy them?

99. If you could choose to have dinner with only 5 people from your real life or imaginary, who would you call and what will be the reason behind that?

100. If someone made a funny comedy movie about your life, which part of the story you think would be the funniest and why?

101. What have you been sorry and feel regret the most of happening in your life?

102. What’s the worst lie you’ve ever told in your life? Did you catch out?

103. If you instantly turned into a woman for a single day, how would you spend that day?

104. When you meet someone for the very first time and you do not like them at all what would you normally do?

So, what else you want to ask your guy or the guy you never meet? Popping any question in your mind? Let us know in the comment box. Ohh, don’t forget to SHARE this with your gang NOW!


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