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110 Deep Questions to Ask Your Boyfriend

List of 110 deep questions to ask your boyfriend to help you jumpstart the talking, and ultimately bring the two of you closer together. Read more ⇣
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Written By Erica
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I'm Erica. I love to help people in their relationships and spiritual lives. I've been through a lot of ups and downs, and I want to share my insights with you.
Deep Questions to Ask Your Boyfriend

It is a known fact that men are not good at expressing their feelings and emotions.

However, there is no reason why you should not try to make him open up to you.

Asking your boyfriend deep questions is a good way to get to know him better. It also gives you an opportunity to see how he thinks and feels about things.

You may find that the answers he gives you are not what you expected. This can be very insightful, especially if it’s something that’s important to you and your relationship.

110 deep questions to ask your boyfriend to help you jumpstart the talking, and ultimately bring the two of you closer together

With all of this being said, I’ve come up with 110 deep questions to ask your boyfriend.

You can use this to get inside your head in strengthening your relationship further and getting to know him better.

110 Deep Questions to Ask Your Boyfriend

  1. Can you remember a time when you changed your values or beliefs?
  2. Are there any things in life that you would be afraid to tell your parents about?
  3. What is the saddest experience you have had in your life so far?
  4. Do you think it is important for people in a relationship to make each other laugh?
  5. What do you usually notice first about a girl when you first meet them?
  6. If someone offered to give you $1 million (about £750,000), but in return, everyone that you know would lose their memories of ever knowing you, would take the offer or not?
  7. Is there something that I’m doing now that makes it harder for us to talk about something serious like this?
  8. What are some things you really hate about your friends?
  9. What is the weirdest thing you find attractive in a woman?
  10. What is the one thing you want to change when you look at yourself in the mirror?
  11. What are your feelings about sharing your password with your partner?
  12. Do you ever compare yourself to other guys? Which qualities do you wish you had?
  13. What would be the one thing that would make life worth living if you had only six months to live?
  14. How important is it for you to make physical contact when showing affection for someone?
  15. How often do you talk about your feelings with people you love?
  16. Who has been your biggest influence in life so far?
  17. f there was one thing that I could do differently as a guy to make my relationship a happy one, what would it be?
  18. What’s one thing that would always put a smile on your face, no matter the situation?
  19. Do you believe everything happens for a reason, or do we just find reasons after things happen?
  20. What’s the worst thing you’ve done and got away with?
  21. What are you most afraid of and what triggered that fear?
  22. At what moment did you realize life wasn’t as simple as you thought it was as a child?
  23. What hobby would you get into if time and money weren’t an issue?
  24. If we were in a group at a party and you told a horrible joke that no one else laughed at, what would you do?
  25. Do you believe that there are things that can’t be understood with logic and reason?
  26. If you could go back in time and relive one day of your life what would it be?
  27. What is a relationship deal-breaker for you?
  28. What are some of your past experiences that have shaped who you are today?
  29. What do you think is the most important value someone can have? Why is it important to you?
  30. What do you wish your parents had done differently when raising you?
  31. What’s your favorite non-sexual thing to do with me?
  32. When you’re old, what would it be worth being remembered for?
  33. If a close friend or family member told you they were cheating on their spouse, what would you tell them?
  34. What is something you saw that was confusing at first but ended up being amazing?
  35. Is there anything you’re secretly worried about at this point in your life?
  36. What has been the biggest change for you so far in the last few years, and how has it affected you?
  37. Do you ever wonder what it would be like to live somewhere else besides where you are now?
  38. Have you ever experienced any kind of psychic phenomenon and if yes, how was the experience?
  39. How have the people close to you changed over the years?
  40. Can you share with me the happy and best moments of your life so far?
  41. What is the most difficult experience you’ve ever had, and what did it teach you?
  42. Do you have pet peeves? If yes, what are they?
  43. Do you think feeling happiness and pain are interconnected with one another?
  44. If a genie granted you three wishes right now, what would you wish for?
  45. If there was one thing about your life that you could change without consequence what would it be?
  46. What is one thing that is important for me to know about your family?
  47. How do you show love for the people close to you?
  48. If you had the power to change one law, what law would you change?
  49. If you were given a choice between loving me and breathing, which would you choose?
  50. If you were stuck on an island for three days, what three things would you bring with you?
  51. If there was one regret that you have in life, what would it be?
  52. If there was one superpower that I could have, what superpower would it be?
  53. How would you describe a perfect date night with me?
  54. What’s the best advice your dad has given you?
  55. What’s the worst advice your mom has given you?
  56. If you could meet anyone in history, who would you want to meet?
  57. What’s the one thing you’ve done that no one else knows about?
  58. Have you ever been hurt emotionally? How did you heal and move forward?
  59. Do you think it’s better to follow your head or your heart when making important decisions?
  60. What advice would you give to someone younger than you?
  61. Do you think human nature is mostly guided by self-interest or altruism?
  62. Do parents have an obligation to keep their kids with them if they’re severely disabled, or is it okay for them to put their kids in foster care instead?
  63. Is making money a top priority for you, or are there more important things in life to focus on?
  64. Are there any issues that can’t be made better through compromise of some kind?
  65. What is something you wish you did more of in your life and something you wish you did less of?
  66. If we had kids one day, how do you think we’d handle parenting them?
  67. Do you think a couple should go to counseling?
  68. Are you socially awkward in real life or on social media? Why do you think this is so?
  69. If you could create a rule that everyone in the world would have to follow, what would it be and why?
  70. Describe your idea of a perfect day.
  71. If I asked you to give me a full body massage, how would you react?
  72. If you had to rate our relationship on a scale of 1 to 10, what number would you give it?
  73. Does it hurt to think about how your parents will feel when they die?
  74. Have you ever saved someone’s life before? And did that make you feel good about yourself?
  75. At what moment in your life have you felt the most fulfilled?
  76. Which is the one thing that has made you stronger than ever before?
  77. Would you like to know the day and hour of your death? Why or why not?
  78. If a doctor told you that only by donating one of your organs would save five other lives, would you do it? Why or why not?
  79. What is your personal definition of success?
  80. What is one thing you would like to change about me if given a chance?
  81. If you could spend one whole day with me and do whatever you wanted, what would it be?
  82. Who was the most influential person in your life for you growing up?
  83. How would your ex describe you? Would you agree or disagree with them?
  84. When was the last time you were really nervous about doing something?
  85. Talk about a time when you felt like an outsider.
  86. Are there any causes that are particularly close to your heart?
  87. Do you feel like I am your best friend or just your girlfriend?
  88. What is the purpose of life according to you?
  89. Do you think our relationship will stand the test of time? Why or why not?
  90. Do you consider yourself to be an emotional person?
  91. How often do you find yourself getting annoyed with people?
  92. How do you define cheating in a relationship?
  93. What is the best decision of your life so far and what makes it so special?
  94. Would you rather be able to see 10 minutes into your own future or 10 minutes into the future of anyone but yourself?
  95. Do you think there is such a thing as a soulmate?
  96. Do you believe in God and life after death, or are we just the product of random chance over billions of years with no greater meaning or purpose for our existence?
  97. Do you believe you tend to hold grudges against people or forgive them easily?
  98. What do you feel is the best decision you’ve made in your life so far?
  99. What’s the biggest lack of faith you’ve ever experienced?
  100. What is a political issue that you’re really passionate about?
  101. How important do you think it is to marry someone of the same religion as yours?
  102. What do you think is one thing all men should do when looking for a partner?
  103. Take four minutes and tell your partner your life story in as much detail as possible.
  104. Is there something that you’ve dreamt of doing for a long time? Why haven’t you done it?
  105. If you could wake up tomorrow having gained any one quality or ability, what would it be?
  106. What is one thing you have done in your life that has made you really proud of yourself?
  107. What is the one thing that makes you feel alive?
  108. When do you feel most free?
  109. What is something random that people don’t know about you?
  110. How important is sharing success or failure with each other at home?


If you want to get to know your boyfriend better, and want to find out more about him, then try asking these profound questions. 

These are deep and substantial questions that can be the most effective in showing you how he thinks, and what he values in life.

Check out my list of deep questions to ask your girlfriend here

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