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120 Deep Questions to Ask Your Boyfriend

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It isn’t always easy finding new things to talk about. When you have just started to date, you may feel tongue-tied and find it impossible to say anything around a guy who used to just be a crush. If you have dated for years, you may quickly run out of things to talk about. These deep questions to ask your boyfriend are designed to help you start a conversation and connect with your boyfriend. Plus, these questions can help you learn how your boyfriend thinks, how well read he is and what he wants out of life. All of these answers can be used to help you improve your relationship and keep the romance alive.

Political and Current Event Questions

1. What is the one thing that small business owners can do to be more successful?

2. Do you think that it is acceptable to require young adults to join the military and go to war?

3. If you were running for president or governor, what are the three things that you would make a central part of your campaign?

4. What do you think is the biggest issue with the military-industrial complex?

5. Should there be laws giving more rights to children?



6. Do you think that there is anything that is too serious to be joked about?

7. What invention do you think has done the most for humanity?

8. Do you think that it is extremely important for someone to do well in school in order to become successful?

9. Do you think that genetically modified food is a good thing?

10. Are you pro-choice or pro-life?

11. What are your political views? Do you side with any particular political party?

12. Why do you think that the divorce rate is so high in the country now? Do you think that there is a way to fix it?

13. Do you think that the way someone looks or dresses says a lot about who they are as a person?



Deep, Serious, and Spiritual Questions

14. Look at your life now. Is there one area of your life that you feel like is missing or that you could work on? What is it?

15. If I was in the middle of giving birth to our child and the doctor says that only one of us can make it, which one of us would you choose to save?

16. Imagine how you dreamed your life would be as a child. Is your life today anything like you expected it to be while growing up?

17. Do you believe that soul mates exist?

18. Who are three people in your life that you would be wiling to give your life for?

19. What is the biggest problem that you are facing in your life right now?

20. If you could return to any moment in your previous existence and give yourself advice, what moment would you return to? Why?

21. Would you rather have the best house in an awful neighborhood or the worst house in a nice neighborhood?

22. When someone hurts you, do you forgive and forget about it or do you forgive and remember it?

23. Would you rather have a happy life full of love or a life full of money?

24. If you were to die in the next day, would there be anything that you regret?

25. Do you believe that it is true that opposites attract? What do you look for in a partner?

26. Would you be willing to let me help you with your problems in life?

27. Where do you think that we go when we die?

28. What would you want people to say about you at your funeral?

29. How do love and affection play a role in your life?

30. Do you believe that everyone is born innately good?

31. Out of everyone in your family, whose death would you find the most disturbing?

32. Do you think that having children is a blessing or just another burden?

33. What is the largest struggle that you have ever faced?

34. Do you think that having a positive outlook on life make any situation better?

35. Tell me about your life story. How did you get to be the person that you are today.

36. Suppose that you have children some day. What would your greatest hope and fear be about them?

37. Do you think that significant others should always be best friends as well as lovers?

38. Finish this sentence. “I wish that I had someone who I could share ____.”

Hard Questions to Make Him Think

39. Imagine that my birthday is coming up, and I want a puppy. Would you get a purebred dog from a breeder or adopt a puppy from the Humane Society?

40. If you were able to fix just one problem in the world today, what would it be?

41. If you could live anywhere in the world and money was not a problem, where would you live?

42. If I were missing and no one ever recovered my body or knew what happened, would you move on or would you spend your life looking for me? If you chose to move on, how long would you wait?

43. If you could have chosen your own first name when you were born, what would it have been?

44. You believe that your neighbor could be abusing their child. Do you stay out of it and mind your own business or call the police?

45. If you could gain one magical ability, what would it be?

46. If you were given just one more week to live and an unlimited amount of money, what would you choose to do?

47. If you had only $200 to spend on a special gift for me, what would you buy with it?

48. If one of your family members needed to have a kidney and you were a match, would you be willing to give up one of your kidneys?

49. If you were able to invite any three people, living or dead, to a dinner, who would it be?

50. What types of advice would you give to someone who was just about to graduate from high school?

51. Would you be willing to sacrifice your life to save a stranger?

52. If your home suddenly caught on fire and you were only able to grab three things, what would you take?

53. If you were given a crystal ball that could tell you anything about your life, the future or anyone else, what would you want to ask it?

54. If you were told that you had a terminal illness, how would you take the news?

55. If you could live in any era in history, what time period would you live in?

Questions to Learn How He Feels About Relationships

56. How important do you think it is to invest your money?

57. Do you think that emotional cheating is just as bad as physical cheating?

58. Do you want to have kids someday once you have the right partner?

59. What are your spiritual views? Why?

60. Do you believe that people can or should be friends with their exes?

61. If one of us had to move out of state or out of the country, would you be able to handle a long distance relationship?

62. What qualities do you look for in a spouse?

63. Do you think that it is more important to spend time with your family or at work?

64. How important do you think that sex is in a relationship?

65. What is your opinion on open relationship?

66. Do you think that it is important for you to save money?

67. What are the three things needed in every successful relationship?

68. What do you believe about premarital sex?

69. What is the one think that you think would automatically destroy a relationship and could never be forgiven?

Personal Questions to Learn About How He Sees Himself and What He’s Like Inside

70. What is your biggest fear about becoming older?

71. Do you pay more attention to the people or the things around you?

72. What are you thankful for?

73. What is your favorite thing about yourself?

74. Would you rather go out or stay in for a date?

75. What inspires you the most?

76. How do you handle failure?

77. If someone calls me something terrible, do you jump in to defend me or let me fight my own battles?

78. When things break, do you replace them or fix them?

79. Would you consider yourself more motivated by external factors versus internal factors?

80. If you were famous, would you enjoy it or would you miss your privacy?

81. If you were able to live until you were 90 and either had the mind or body of a 30-year-old, what would you choose?

82. If you were given three wishes, what would they be?

83. If you were offered $2 million on the condition you gave up all your family and friends, would you take it?

84. Do you feel that you are materialistic?

85. What would be your perfect date night?

86. Do you think that it is okay to have close female friends when you are in a relationship?

87. If you could change anything about yourself, what would it be?

88. What is the one thing that you absolutely cannot start your day without?

89. Would you rather be buried or cremated after you die?

90. You notice an old man living in a shopping cart. What is the first thought that comes to your mind?

91. What are three things that you are willing to splurge on?

92. When you are under stress, how do you relax?

93. Do you ever rehearse what you will say on a phone call before you call someone?

94. What are some things that offend you?

95. Is there something that you have dreamed about doing for a long time? Why haven’t you done it?

96. Would you rather live in the moment or prepare for the future?

97. What is one thing that no one else knows about you?

98. Do you think that you are an optimist or a pessimist?

99. What would you consider a perfect day?

Questions to Learn About Your Relationship and How He Feels About You

100. Do you think that stay-at-home moms or career moms are more admirable?

101. Is there anything that you would never compromise over?

102. When did you first realize that you wanted to date me?

103. What are three things that you think that we have in common?

104. What was your first impression of me?

105. What fictional or famous couple reminds you of us?

106. Would you rather leave a big impact on the world or on your family?

107. Would you rather be good in the bedroom or good in the kitchen?

108. What do you appreciate the most about me?

109. What song do you think describes our relationship?

110. Would you rather surprise me with an expensive gift or consult me first to make sure that I will like it?

111. Is there anything in our relationship that you think we should work on?

112. Do you think that a proposal should be a private intimate moment or a public display?

113. Are you looking for a commitment?

114. What are the biggest differences between us?

115. If we had children, which features would you want them to inherit from me and which from you?

Questions to Know More About His Past

116. When was the last time that you were in love?

117. What is your worst memory?

118. What is your happiest memory?

119. Have you ever done something you regretted?

120. What is a tradition you did as a child that you would want your children to share?

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