Eager to get close to your guy? Try asking him some of these deep personal questions, you will find out some hidden secrets about him. At first the questions might sound funny or uncomfortable, but by the time he starts answering, a lot of mysteries are going to be unraveled and you will get to know him better. Here we have a huge list of such questions.

100+ Deep Personal Questions To Ask A Guy or Boyfriend

1. What are some of the morals you live by?

2. What is your goal in life?

3. Do you like the lights on or off?

4. Do enjoy one on one outings or do you prefer big groups?

5. What is your favorite body part on a female?

6. What is one thing you don’t like about me?

7. Are you a virgin?

8. How many times have you been in love?

9. Have you ever longed for a woman that was much older than you?

10. What is the worst date you’ve ever been on?

11. What is a deal breaker for you?

12. Are you religious?

13. What is your strangest habit?

14. Have you ever had a wet dream?

15. Are you financially stable?

16. Do you usually stay friends with your exes?

17. Have you ever lost someone close to you?

18. If you are in a bad mood, do you prefer to be left alone or have someone to cheer you up?

19. What’s an ideal weekend for you?

20. What do you think of best friends of the opposite sex?

21. Do you judge a book by its cover?

22. Are you confrontational?

23. Do you consider yourself an introvert or an extrovert?

24. Which parent are you closer to and why?

25. What was the best phase in your life?

26. What was the worst phase in your life?

27. Is what you’re doing now what you always wanted to do growing up?

28. What makes you feel accomplished?

See Also: 110 Really Stupid Questions To Ask People

29. What is the most embarrassing thing that has ever happened to you?

30. What is the biggest lie you’ve ever told?

31. Would you give up a poker night with the boys to take care of your sick girlfriend?

32. What would you do if your ex-girlfriend suddenly wanted to get back together?

33. What do you think of open relationships?

34. What’s your favorite book/movie of all time and why did it speak to you so much?

35. What is a relationship deal breaker for you?

36. Are you more into looks or brains?

37. Would you ever take back someone who cheated?

38. How do you feel about sharing your password with your partner?

39. When do you think a person is ready for marriage?

40. Do you have any phobias?

41. What makes you angry?

42. What is your deepest, darkest secret?

43. Have you ever wanted to be a woman?

44. What is one question you absolutely refuse to answer?

45. What are you most insecure about?

46. What does love mean to you?

47. What kind of parent do you think you will be?

48. What would you do if your parents didn’t like your partner?

49. Who is that one person you can talk to about just anything?

50. When was the last time you broke someone’s heart?

51. Did you ever write a journal?

52. What are you most thankful for?

53. Do you believe in second chances?

54. What’s the one thing that people always misunderstand about you?

55. What is your idea of a perfect vacation?

56. What did your past relationship teach you?

57. What are your thoughts on online dating or tinder?

58. What’s on your bucket list this year?

59. When have you felt your biggest adrenaline rush?

60. Would you relocate for love?

61. Do you have any enemies? Why?

62. On a scale of 1 to 10, how would you rate me?

63. How did your last relationship work out?

64. What is your dream tattoo?

65. What is the craziest thing you’ve ever done and would you do it again?

66. If a genie granted you 3 wishes right now, what would you wish for?

67. What’s your biggest regret in life?

68. What do you think about when you’re by yourself? TC mark

69. What’s your biggest fantasy?

70. What is your biggest turn on?

71. What is your biggest turn off?

72. How many girls have you been with?

73. Have you ever cheated on a girlfriend?

74. Have you ever had a one night stand?

75. Who is the most important person in your life?

76. What are you attracted to in a woman?

77. What’s your philosophy in life?

78. What’s the one thing you would like to change about yourself?

79. Are you religious or spiritual?

Also See: 100 Good Questions To Ask Your Crush

80. Who is your favorite family member/sibling?

81. Do you like to talk dirtily on the phone or online?

82. What about your pet peeves?

83. What was the worst lie that you told your parents?

84. What is your happiest memory from the past?

85. How do you spend your week?

86. Do you ever feel the need to have total privacy?

87. What are the things that you like to do alone?

88. How would you describe your version of a perfect home?

89. If one song were to describe your life, what song would it be?

90. If you ever got into a disagreement with any one of my family members or best friends, how would you deal with it?

91. Do you have any close female friends, other than me and any of your female family members?

92. Do you have feelings for any of your ex-girlfriends or a best friend who you liked in the past?

93. Everyone has regrets about their past. Which is the one thing in your past you would like to change?

94. What did you think of me, when we first met (be honest)?

95. How do you think you would react if you found out I was cheating on you?

96. How would you find out or realize if there is no one more perfect for you than me?

97. Are you a person who keeps enemies, grudges or any negative thoughts about a person?

98. Where and how serious do you see the both of us as a couple in five years?

99. What are the experiences that have made you, who you are today?

100. What according to you is a perfect life, and how you would you try to make it for yourself and me?

101. What do you think is the best quality in me, which attracts you?

102. What is that one thing in me, which you would like to change if given a chance?

103. Would you ever consider moving in together, and if you do, how comfortable would you be with privacy?

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