100+ Deep Questions to Ask a Guy to Get Him to Open Up

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deep questions to ask a guy

It is an open truth that men rarely open up about their emotions, lives or past.

According to this article on Medium, it is even harder for men raised in hardened backgrounds or those with strong Christian or traditional beliefs to open up and share what they feel, think and sometimes what they are doing.

But how do you make your guy open up about his life without making him feel intruded? Well, asking the right sets of questions at the right time has been known to work time and again.

In a question game manner or playing cards, asking the right questions will give you a good peek into your man’s life in a way direct probing will never do.

In this article, I came up with the right sets of deep questions to ask a guy that will get him talking. They range from normal life questions to flirty ones and in some instances very deep and personal ones. Have fun!

100 Deep Questions to Ask a Guy

Here are your deep questions to ask a guy and get him talking. They are ideal for a crush you just met, your boyfriend or for couples trying to explore more about each other. Enjoy.

1. What do you consider a waste of time?

2. How do you define a life wasted?

3. What is your life philosophy?

4. How do you define love?

5. What relationship advice would you give a younger you?

6. What is your take on relationships and sex?

7. How do you define a successful life?

8. How do you measure progress in life?

9. What is your love language?

10. In what ways do you achieve happiness for your life?

11. What is your take of the debate between beauty and brains?

12. What lessons have you learned as far as relationships are concerned?

13. Whose love life do you consider near perfect?

14. How do you want your relationship to be?

15. What do you think is a waste of one’s precious time?

16. What book did you read last?

17. What book genre do you prefer the most?

18. What music genre do you listen to?

19. Who is your favorite musician?

20. What are some of the life luxuries under your possession?

21. What do you consider as necessary little life luxuries?

22. What song touches your heart every time you hear it?

23. What are some of your expensive habits?

24. What is your all-time best movie?

25. What movie would you advise everyone to watch?

26. What book would you advise everyone to read before they hit 40 years?

27. What do you consider a good life?

28. Is there a connection between money and happiness?

29. How fulfilled are you with your current state of life?

30. Do you think polygamy to solve a single-parenting issue is a good idea?

31. Apart from masturbation, how else do you pleasure yourself?

32. Do you sometimes feel capitalism is destroying our planet?

33. What is your take on the existence of another intelligent life form in the galaxy other than humans?

34. Can socialism be part of the solution to a contended society?

35. Which book shaped a large part of your life?

36. Do you think love is a one-way highway?

37. Is the country going in the right direction?

38. Who are you likely to vote for in the upcoming elections? Why?

39. Should there be a limit to the amount of wealth an individual should have?

40. Which society do you feel is the best to raise a family?

41. Do you stay friends with your exes?

42. What type of parent do you think you will be?

43. Do you sometimes judge someone by how they look and carry themselves?

44. What do you feel most thankful for in life?

45. What do you do when angry?

46. What is in your bucket list for this year?

47. What are some of your biggest regrets in life so far?

48. What worries you often?

49. What do you mostly think of when alone?

50. What are some of your favorite hobbies?

51. What do you think is a waste of time?

52. What do people say about you that you disagree with?

53. Can you describe three of your best friends?

54. How do you spend your ‘quality time alone’?

55. Do you have phobias?

56. Do you think I love you enough?

57. Do you feel understood most of the time?

58. Do you feel loved by the people around you?

59. What did you learn from your father?

60. What is your greatest fear in life?

61. What keeps you awake late at night?

62. What terrifies you every time you think about it?

63. What is your favorite drink?

64. What sport do you like the most?

65. What indoor game do you think you are unbeatable?

66. Do you believe giving friends small gifts every now and now is a good thing?

67. How long is your longest relationship?

68. Have you ever taken someone’s virginity?

69. At what age did you first have sex?

70. What is the shortest relationship you have ever had?

71. Have you ever had a pet?

72. When is the last time you took a charitable cause of action that made you feel fulfilled?

73. How good are you at dancing?

74. What risks have you ever taken?

75. Do you think people around you see you for what you are?

76. What are some of the things people don’t understand about you?

77. What are some of the biggest regrets you have in life?

78. If you are to die today, what will you be remembered for?

79. What are some of your past lives you wish to forget?

80. What are some of the strangest nightmares you have encountered in your dream?

81. Who is your favorite person in the world?

82. Whose life would you like to emulate?

83. Do you sometimes work out? Do you think it is healthy to workout once in a while?

84. Is it a good thing to tell a lie if it serves the greater good?

85. Apart from my body and looks, in what other ways do you find me attractive?

86. Do you believe in life after death?

87. Do you think we can be soulmates?

88. What do you consider important in your life?

89. Who are the most important people in your life?

90. In what ways have you changed in the past five years?

91. What are some of the bad decisions you have made recently?

92. Am I romantic enough?

93. Do you like these deep questions to ask a guy?

94. How likely are you to suggest these deep questions to ask a guy to one of your close friends?

95. How likely are you to play these deep questions to ask a guy again soon?

96. Are all people equal in the world?

97. Is money the source of all evil in the world?

98. Do you think true love exists?

99. What are some of the small things that matter in life?

100. What are some of your expensive small habits?

There you have a list of deep questions to ask a guy. You can ask them in person face to face or over text for long distance relationship. Make sure to be nice and have fun while asking.

More Questions to Ask a Guy:

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Dirty Questions to Ask a Guy

Questions to Ask a Guy (A Complete List)

Deep Questions to Ask a Guy