100 Deep Questions to Ask Your Boyfriend

100 Deep Questions to Ask Your Boyfriend

Deep Questions to Ask Your Boyfriend Photo
Photo by Andrea Piacquadio from Pexels

All relationships that last a lifetime have one thing in common – an understanding for each other and respect that comes with it.

There is no better way to know and understand how your boyfriend or girlfriend feels about you and the direction your relationship is taking than by asking subtle questions every now and then.

One BIG mistake we commit most often is assuming that everything is right. Just because you are happy and no issues are popping up doesn’t mean everything is okay.

There is a need for you to get to know each other in a more meaningful way especially when everything seems to be going in the right direction.

In this article, I have prepared a list of deep questions to asked your boyfriend over text or in-person the next time you meet.

Unlike fun questions, deep questions to ask your boyfriend help you understand your position in the relationship, how much you are valued and the direction the whole relationship is taking.

100 Deep Questions to Ask Your Boyfriend

Here is your list of 100 deep questions to ask your boyfriend at any time. They are short for in-text conversation and simple enough for him to understand without the need for explanations.


2. Who am I to you?

3. What are we?

4. Do you love me?

5. What is love to you?

6. Am I romantic?

7. What is romance to you?

8. What makes me different from any other person out there?

9. How comfortable are you introducing me to your parents and siblings?

10. Would you like to see my parents and siblings?

11. In your view, what will your mother think of me?

12. Do you wish to have kids soon? When is that and how many kids?

13. What makes you stand out above other people around you?

14. Do you think we would be together if you become a billionaire?

15. Do you have a best friend in life apart from your girlfriend?

16. What are you mostly misunderstood for?

17. Who is your role model?

18. How much do you love me?

19. Do you think we have a future together?

20. How long was your longest relationship?

21. How short was your shortest relationship?

22. When last did you have a serious relationship?

23. When was the first time you had sex?

24. Have you ever stayed with a partner for more than three months?

25. Have you married before?

26. Have you ever been engaged?

27. Do you still remember where we met, how and what happened that day?

28. What is your view on the current political scene?

29. Will you vote this coming election?

30. What are you voting for?

31. Tell me more about your dreams and aspirations in life.

32. What are you most afraid of?

33. Do you honestly think money can buy happiness?

34. To what extent can money buy love?

35. What accomplishments are you most proud of this far?

36. What is the one thing you want to accomplish in your lifetime?

37. Do you have any addiction?

38. Have you ever used hard drugs before?

39. Are you introverted or extroverted?

40. What is your personality type in the 16 personality types?

41. What do you do when mad at someone?

42. Do you hold grudges?

43. Have you ever been in a relationship you considered abusive before?

44. How likely are you to forgive cheating in a relationship?

45. Describe yourself in 3 words?

46. Which one word describes you the most?

47. Do you have a nickname? What is it?

48. How is your typical weekend?

49. What are you currently working on as far as a better future in for yourself is concerned?

50. What are your views on polygamy?

51. What do you do when feeling low?

52. What are your preferences between blue color executive job Vs. SME entrepreneurship?

53. Choose one between political career vs. business?

54. What is your favorite music?

55. What are your life values?

56. Who or what inspires you the most?

57. What did you first think of me when we first met? Has anything changed since then?

58. What are your favorite memories of us so far?

59. What is in your bucket list for us this year?

60. What is the one thing you feel our relationship is lacking?

61. What made you fall in love with me?

62. What are you most scared to ask me yet you want to know the answer?

63. What secret have you been wanting to tell me but often find it hard?

64. How would you love to receive affection?

65. What is the biggest strength of our relationship?

66. What was your most vulnerable moment in our relationship?

67. What are your goals in this relationship?

68. What do you want the world to remember you for?

69. What habits do you find yourself struggling with right now?

70. What is the most important lesson you have learned so far in regards to relationships?

71. What lesson have you learned t so far as life is concerned?

72. What is the most dangerous decision you have ever taken? How did it end?

73. If you have to change one thing about your past, what will it be?

74. What are the biggest lessons you learned from the previous relationship?

75. What are your thoughts on having a family in the next five years?

76. What is the worst gift you have ever received?

77. When young and growing up, what did you want to be? Did you try to achieve it?

78. What would you change in our relationship as it stands right now?

79. Who loves more in our relationship?

80. How much do you value me?

81. How much do you value our relationship right now?

82. Are we soulmates?

83. How would you prefer I express my love for you?

84. What secret haven’t you told me yet?

85. What have you wanted to ask but never found the right time?

86. What gets you frightened in our relationship?

87. What frightens you the most when it comes to love and relationship?

88. Are we compatible partners?

89. Have you been open with me so far?

90. Why did you fall in love with me?

91. What memory of us makes you smile instantly every time?

92. Do you believe in true love?

93. Do you believe in love at one sight?

94. Who is your hero? What qualities make your hero?

95. Would you rather be rich and lonely or be poor and be loved very much?

96. Who was your first girlfriend? What happened between you two?

97. How much has your life and relationship priorities changed over time?

98. What do you look for in a spouse?

99. What is your view on open relationships?

100. Do you think people should be close friends with their exes?

There you have your complete list of deep questions to ask your boyfriend. Feel free to print your copy and have a blast the next time you meet.

Remember the deep questions to ask your boyfriend is a step towards understanding each other is a more meaningful way.

More Questions to Ask Your Boyfriend:

Good Questions to Ask Your Boyfriend

Funny Questions to Ask Your Boyfriend

Freaky Questions to Ask Your Boyfriend

Dirty Questions to Ask Your Boyfriend

Deep Questions to Ask Your Boyfriend

The Smartbackyard