140 Deep Questions To Ask Your Boyfriend

Ever wished you could connect with your boyfriend more emotionally? Here are 140 deep questions to ask him to help you achieve this.

By Emmanuel Onitayo
140 Deep Questions To Ask Your Boyfriend

Relationships Are Built And Not Bought

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No amount of money can buy a good relationship. It's simply priceless. Parties involved have to make a mutual sacrifice to make it work. And one of such sacrifices entails asking the right questions. Questions have a way of connecting hearts together, especially ones that are deep. A question is considered deep if answering it would elicit more information than the question literally carries on the surface. As you ask your boyfriend questions and he responds, something happens to you both. You both get closer and learn more about each other. You are better aware if you both are intellectually compatible because the deep questions would make him think and from his thoughts, you get to know who he is. So, straight to business. Here are those deep questions to ask your boyfriend.

Questions To Ask Your Boyfriend To Get His View Of Life

1. Does it bother you that you’re growing older daily? 2. Ever been in a situation that you will be eternally grateful for? 3. Have you been dreaming of accomplishing some specific goals for some time now? 4. Have you ever had the opportunity to sing for yourself or someone else? 5. Do you think it's right taking one's life because of life challenges? 6. Would you prefer me writing you a letter or sending you an e-mail? 7. Do you think a truth or dare question matters in a relationship? 8. In your opinion, how much is too much to spend on a wedding ceremony? 9. Can you tell if someone is being original or pretending? And how? 10. Do you see yourself as an optimistic or a pessimistic person? 11. What is your source of motivation during bad moods? 12. Do you prefer people to be cremated or buried? And why? 13. What are the things that irritate you the most? 14. What do you do to ease your stress? 15. What is your definition of having a perfect date? 16. Do you like amassing wealth? 17. Can you describe your personality in three words? 18. Do you prefer repairing faulty appliances or replacing them with new ones? 19. Do you love meeting new people? 20. Do you have the mental strength to cope with failure? 21. What truth or dare scenario have you found yourself in life? 22. Do you think you are a self-motivated person? 23. Have you ever failed or messed up something or someone before? 24. What do you love most about yourself? 25. If you have the opportunity of changing something about yourself, what would you change? 26. If you have the opportunity of making three wishes, what would the wishes be? 27. What are the principles you think relationships should rest upon? 28. What can you not miss doing or getting involved in every day? 29. What is your take? Living on what is presently available or saving the best for the appropriate time? 30. How do you cope with conflict?

Hard And Trivia Questions To Make Your Boyfriend Think

31. If you were the president of our country, what would you do on the issue of gender equality? 32. If you have the opportunity of having a second wife, what qualities would she have? 33. Suppose you were given a huge sum of money to spend, would you spend all of it on me? 34. If you were told that I am pregnant, what would your first reaction be? 35. Can you sacrifice your job for the love you have for me? 36. If you had the power to recreate me, would you still create me like this or into something else? 37. Let’s say you are to attend a dinner with three girls, what would those girls look like? 38. If you had the opportunity of choosing where you were born, where would you have chosen? 39. If you have the chance of choosing your parents all over again, do you see yourself choosing your current parents? 40. If you are famous today, how would you manage your fame? 41. What would your advice be for someone who failed his entrance exam? 42. What would your advice be for someone who lost his / her both parents on the same day? 43. What would your advice be for an individual who has been without a job for about five years? 44. What would your advice be for someone who just got into a relationship? 45. How would you advise someone who is broke and has nothing to do for a living? 46. What would your advice be for an individual who is easily angered? 47. What would you do to help someone suffering from an illness? 48. What would you do for someone who has the intention of lying to you? 49. What would you do for someone who saved your life from a dangerous animal? 50. What would you do if you were in a situation of saving just one of these people: a baby, your mother, or your best friend?

Questions To Ask Your Boyfriend To Get His Views On Relationship Issues

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51. What is your definition of a perfect relationship? 52. Can you sacrifice your life for your wife and children? 53. Do you prefer a long distance relationship to a closer one? 54. What is your perfect description of a happy home? 55. What do you consider essential to a long-lasting relationship? 56. Do you love being with children? 57. Which do to you prefer, a couple having a joint or private bank account? 58. What is your view about sex in marriage? 59. Do you believe marrying someone’s best friend makes a happy home? 60. Do you think a long distance relationship has a larger percentage of survival? 61. What are the qualities you expect to see in your spouse? 62. Do you believe in sex before marriage or sex after marriage? 63. Do you think cheating is bound to happen in any relationship? 64. What is your idea of an open relationship? 65. Do you believe in saving money or investing it? 66. What is the sign to watch out for in a relationship to make it last? 67. Do you think it is good to still be in touch with someone’s ex? 68. Do you prefer a housewife or a career wife? 69. Would you give room for family influence in your relationship? 70. What is your description of a perfect weekend with one’s family?

Questions To Know How He Feels About You

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71. If everyone were to be asked to come to their places of work with their girlfriend, would you be proud to take me along? 72. If you were to write me a letter on my birthday, what would the content be like? 73. What was the first impression you had towards me? 74. What got you attracted to me? 75. Would you rather seek my opinion before buying a gift or you prefer springing up surprises? 76. What do you love most about me? 77. What do you dislike most about me? 78. If you have the power of giving me a talent, what talent would that be? 79. What kind of clothes do you love seeing on me? 80. Do you love my family and friends? 81. Can you donate one of your kidneys to save my life? 82. How would you like us to take care of our children in the future? 83. When was the first time you started thinking of being with me? 84. To what length or extent can you go to show that you truly love me? 85. If your friend or a family member told you to break up with me because they don’t like me, what would you do? 86. Would you rather rebuke those that are gossiping about me or just walk away? 87. How do you feel anytime you see guys checking me out? 88. How would you describe me in just three words? 89. Do you love me asking you some truth or dare questions? 90. Do you feel we need to change some things to make our relationship work out?

Some Political And Truth Or Dare Questions To Ask Your Boyfriend

91. Do you believe that beauty is in the eye of the beholder? 92. Considering the cons of social media, do you think it should be limited? 93. If you are to make a law on gay marriage, what would your decision be? 94. Is politics really a dirty game? 95. What is the essence of going to school when many successful people are impacting the economy of the country with little or no education? 96. Do you think that outward dressing reveals the person you are inside or not? 97. Are you proud of your country? 98. Do you think it is good for kids to be using cell phones? 99. What is your stance on religion and politics working together? 100. Should transgenders be given equal rights as a normal human being?

Questions To Know Of His Past Experiences

101. What did you aspire to become when you were still a teen? 102. When did you first experience loving a girl? 103. When did you first say “I love you” to a female friend of yours? 104. Are you ashamed of your past? 105. How did you relate to your peers in high school? 106. Do you have any past experience that is worth sharing in a book? 107. Ever written a love letter before? If yes, to who? 108. What one letter have you received in the past that has changed your life positively? 109. What experience did you have as a kid and you wish your kids could have? 110. Describe your first date experience. 111. Do you wish you had the power to change your past? 112. How do you see yourself in the next 30 years? 113. Can you recall the last time you cried? Why and because of what? 114. Describe your happiest moment. 115. What is the moment you’ve spent with me that you can never forget? 116. Has your look changed since you graduated from high school? 117. What is your stand on husbands maltreating their wives? 118. Have you ever learned to stop a habit in a hard way? 119. Who was your hero as a kid, Superman or Spiderman? 120. Do you have a criminal record?

Questions To Know His Stand On Moral Issues

121. Do you think everyone has the mind of being good to others? 122. How easily do you forgive and forget? 123. Do you believe in love at first sight? 124. Would you prefer having lots of money to finding a true love? 125. Do you wish to live amidst people or isolate your house from people? 126. What would come to your mind seeing me early in the morning in front of your house? 127. Do you really think school is worth it? 128. Do you believe that we shall all die? 129. Do you believe that there is life after death? 130. Do you prefer me looking natural or make use of makeup? 131. Do you have a life story to tell your kids? 132. What role would you love to take if you were an actor? 133. What is the biggest challenge you have ever been faced with? 134. Do we have anything in common? What are they? 135. What is your view on heaven and hell? 136. Do you attend church regularly? 137. Who should be more committed to a relationship, the guy or the girl? 138. Do you love watching comedy films? 139. Would you force me to attend the same church with you? 140. Do you love pets being around you?

To Wrap It Up

For these set of questions to be effective in achieving your aim, you need to present them to your boyfriend in the proper way. You don’t make him feel as if you are obligating him to answer them. Ask the questions during your normal conversation. Do not bombard him with too many questions. If you follow the necessary principles, you will get more answers than you are even expecting from him.


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