100+ Freaky Questions to Ask Your Boyfriend

100+ Freaky Questions to Ask Your Boyfriend

Freaky Questions to Ask Your Boyfriend Photo
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Your list of the best freaky questions to ask your boyfriend at any time in-person or over a text message.

An unemotional relationship is as boring as it is dead even when all other relationship parameters are all green.

But how do I make my relationship emotional and not a boring one?

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Ask wacky questions.

In as much as you get to know each other better, freaky questions are emotional in nature.

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Most often, they seek deep answers on things we rarely think of but are very important for a healthy relationship like “who am I to you?”

In this article, we came up with some of the best freaky questions to ask your boyfriend at any time, be it in person or over a text message.

The aim of the questions is to not only have fun and know each other better but also to know your position in the relationship and if there is a future for you two.

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Freaky Questions to Ask Your Boyfriend Over Text (or In-Person)

Here is a complete list of unique freaky questions to ask your boyfriend over text or in person.

You can copy and paste the most appropriate questions to your text messaging app for your boyfriend at any time.

You can opt to print your copy for intentional discussion when you meet next time and fun at the same time.

Here are your 100 freaky questions to ask your boyfriend:

1. Do you keep tabs with your exes?

2. Have you ever cheated on me?

3. What are your innermost fears about us?

4. How many girlfriends have you had so far?

5. Who is your best girlfriend ever?

6. Who among the persons you have ever dated built the most memories with you?

7. Why do you love me?

8. What is the worst response you have ever received for “I love you”?

9. Have you ever dated more than one lady at the same time? What happened in the end?

10. Have I ever broken your heart?

11. What do you think I should change about myself first?

12. Which part of me do you wish could be better?

13. What do you admire the most out there that I might be lacking in?

14. If you are to re-live a day in your life, which day would it be?

15. If you are to re-live just one moment with me, what moments will that be?

16. On a scale of 1-10, how likely are you to have me as wife?

17. What do you think the future holds for us?

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18. What have you wanted to tell me but never find courage?

19. Have you ever tried dating someone else while we are still in a relationship?

20. Who is your celebrity crush? What makes you have a crush on her?

21. Who is the most beautiful person you have ever seen?

22. When last did you text your former girlfriend?

23. Do you have a crush on anyone at the moment? If yes, who are you crushing on?

24. Whom do you think is most likely to to ask for a break up first?

25. Who do you think loves more?

26. Have you ever cheated on someone in your love life?

27. What is the best outfit you ever seen me wear?

28. What outfits would you not prefer I wear?

29. On a scale of 1-10, how much do you like me with makeup on?

30. On a scale of 1-10, how beautiful am I?

31. On a scale of 1-10, how smart am I?

32. Does the idea of having someone staying with you in the same house sound good?

33. What are your views on polygamy?

34. What will you do if you find me cheating on you?

35. What will you think of me if you find out I am still in communication with my ex?

36. What is love to you?

37. Do you feel I love you enough?

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38. What puts you off often as far as I am concerned?

39. What lessons has life tough you so far?

40. What are your values in life?

41. What is your worst experience of a heartbreak?

42. Is it okay to lie to the person you love if it is for their own good?

43. What is your take on confrontations in a relationship?

44. Do you take drugs sometimes?

45. What drugs have you ever been on in the past three years?

46. Have you ever had a scary moment with your girl? What was it?

47. What is the one thing that got you attracted to me?

48. Do you think I am beautiful?

49. Do you think I am in the same class as you?

50. What do your friends say about me?

51. Have you ever thought of dumping me?

52. What is the worst you have ever heard about me?

53. What is the worst comment you have ever heard concerning me?

54. Have you ever felt like I am growing distant from you?

55. When is the last time you felt jealous when I am around another guy?

56. What is the one secret you have never told anyone in your life?

57. Does your family know anything about us?

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58. Do you think your mother will like me?

59. Have you ever bragged to your friends about me? What did you brag about?

60. When do I look more beautiful to you?

61. What if I proposed to you right now?

62. What will you think of me if I propose to you?

63. Can you share with me a few examples of your dirty talk?

64. What is your opinion of a possessive relationship?

65. Have you ever owned an adult toy?

66. When last did you m#sturb#te while we are in a relationship?

67. Would you prefer big bottoms or bigger bursts?

68. What have you ever wanted to say to me but always felt it is inappropriate?

69. What is your opinion of a dp?

70. What is your take on a 3s#m?

71. How likely will you accept us not having anything until marriage?

72. Have you ever felt like I am ending the relationship? Did it freak you out?

73. How comfortable will you be if I asked for a breakup right now?

74. Do you think I am romantic enough?

75. What is your idea of a perfect relationship? How do we fare?

76. Do you still have your exes numbers on your phone? If yes, how many?

77. What is your thought on an open relationship?

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78. What are your thoughts on a possessive girlfriend? Is it romantic or not?

79. What is your best experience of us that you will never forget?

80. Do you like it when I am the one initiating it every time?

81. How willing are you to meet my parents?

82. How do you feel when we are apart?

83. Why do you think fate brought us together?

84. Do you think we can ever reach soulmates status?

85. Do you remember the exact date, place and time when we first met?

86. What was your first impression of me when we first met? Has anything changed?

87. What are some of your opinions about me that have changed over time?

88. Why do you love me?

89. What am I best at between intimacy, romance and kissing?

90. What will you do if you learn I cheated on you at one time?

91. What would you never want I do to you?

92. Would you kiss me in public?

93. Would you kiss me in front of your best friends?

94. Can I go through your chats with your buddies?

95. Who are you most likely to cheat on me with?

96. Do you like the kind of friends I have?

97. How okay are you with me being friends with guys?

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98. What is one quirky thing about me that you love?

99. Would you risk your life to save mine?

100. Do I make you happy?

There you have your complete list of 100 freaky questions to ask your boyfriend. Have fun asking!

More Questions to Ask Your Boyfriend:

Good Questions to Ask Your Boyfriend

Funny Questions to Ask Your Boyfriend

Deep Questions to Ask Your Boyfriend

Dirty Questions to Ask Your Boyfriend

Freaky questions to ask your boyfriend

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