100 Deep Questions to Ask Your Boyfriend

Being in a relationship is a beautiful feeling and having a good partner makes it more beautiful. 

When you’re dating a guy you like, you can notice that you don’t know him as well as you’d want. It’s possible that your boyfriend is difficult to read, or that you’re fresh to the relationship and want to learn more. 

Whatever your scenario, having a chat with your boyfriend, observing him in various situations, and interacting with him can all help you discover more about him.

I have listed 100+ questions you can ask your boyfriend.

Deep questions to ask your boyfriend

  1. What would you alter about me if you had the chance?
  2. Men or women, do you believe, have it tougher?
  3. What are your concerns for the future?
  4. What about you most frightens you?
  5. What was the most terrifying dream you’ve ever had?
  6. What causes you to become extremely emotional?
  7. What is the quickest way to irritate you?
  8. What would it be like to live in your own little hell?
  9. What’s your softness level?
  10. What is the most banal task you have mastered?
  11. On a regular basis, what creepy or cringey activity do you do?
  12. What peculiarities does your body possess?
  13. Can you tell me a brutally honest truth about yourself?
  14. How much of what goes wrong in your life is your fault?
  15. How does it feel to be you?
  16. What do you consider to be the best time in a person’s life?
  17. What do you believe has become overly socially acceptable?
  18. What is the nastiest thing you’ve ever witnessed?
  19. What is the most worthwhile activity a person can engage in?
  20. What kind of behaviour makes you think someone is well-dressed?
  21. What is the worst experience that everyone should have to go through?
  22. What would you like to be able to stop doing?
  23. What event accelerated your personal growth the most?
  24. Who do you believe is the most attractive person you can think of?
  25. Can you explain to me how menstruation works and why it happens?
  26. Can you explain me why it appears like the sun rises and sets?
  27. Can you think of ten female authors?
  28. What is your favourite outfit that you’ve ever seen me in?
  29. What’s the most amusing thing I’ve ever said to you?
  30. What is your favourite feature of mine?
  31. Do you believe I’m more successful in my career or in my personal life?
  32. Why would you choose to be a stay-at-home parent over a working parent?
  33. Do you still text with any of your ex-boyfriends or girlfriends?
  34. What about a woman appeals to you the most?
  35. What is your most crazy ability?
  36. What is it about you that everyone always gets wrong?
  37. How do you unwind after a long day?
  38. Who do you look up to as a role model?
  39. Which celebrity do you most want to meet?
  40. What is one thing you’ve never been very good at?
  41. What is the one thing about a woman that you always notice first?
  42. Which of your childhood memories is your favourite?
  43. What is the one thing about a woman that you always notice first?
  44. Which of your childhood memories is your favourite?
  45. What have you accomplished that you are really proud of?
  46. What have you done that you’re not very pleased with?
  47. What has been the most terrifying thing you’ve ever done?
  48. Which sport would you choose if you could be a pro at anything?
  49. Who would you marry if you could only marry one celebrity?
  50. Why do you consider your best buddy to be your best friend?
  51. What do you consider to be the best aspect of being in a relationship?
  52. Which animal is your favourite?
  53. When you need to relax, where do you prefer to go?
  54. Do you prefer to work out at the gym or at home?
  55. What was the most recent event that caused you to cry?
  56. What is one thing a lady could do that you would never forgive?
  57. Have you ever had a friend betray you?
  58. What do you like best about your friends?
  59. What was the first time you met your best friend?
  60. On a first date, what question do you always ask women?
  61. Do you wish to have children?
  62. What is your ideal automobile?
  63. What is the title of your favourite book?
  64. What is the most dreadful film you’ve ever seen?
  65. Which superpower would you most like to have?
  66. What is the most enjoyable activity you’ve ever shared with your friends?
  67. Do you have a stronger bond with your mother or father?
  68. Which member of your family is your favourite?
  69. What do you consider to be your most outstanding accomplishment?
  70. What’s the strangest habit you have?
  71. What is your most terrifying fear?
  72. Which condiments do you keep in the fridge and which do you keep in the pantry?
  73. What are some non-traditional ice cream toppings that you think would be fantastic?
  74. How much ice cream should you put on an ice cream cone?
  75. What kinds of employment might particular animals be uniquely qualified for if they were as clever as humans?
  76. Is it true that fish have necks? Am I your fish?
  77. If you ever get wealthy, what crazy things will you do?
  78. What would the world be like if there were health potions?
  79. What was the last item you looked up on Google?
  80. What’s a cheesy joke you tell all the time?
  81. What’s the strangest wrong-number text or call you’ve ever received?
  82. What would keep you from accepting immortality if it came with a condition?
  83. What would be the most epic name you could choose if you could alter your first name?
  84. What’s the most creative “who would win in a fight A vs. B” you can think of?
  85. What sentence could you utter to everyone in your country at the same moment that would instantaneously make the largest number of people detest you?
  86. What makes you want to start a family?
  87. What’s the worst situation you’ve ever found yourself in?
  88. What is the most thoughtful thing a woman has done for you?
  89. What is your biggest dating stumbling block?
  90. What is your earliest recollection from childhood?
  91. What is one thing that consistently irritates you?
  92. So far, what has been your proudest achievement?
  93. What is one aspect of your current location that you adore?
  94. What is one feature about your current location that you despise?
  95. What is your favourite Starbucks drink?
  96. What would you get if you could only get one present?
  97. If you ever get wealthy, what crazy things will you do?
  98. What would the world be like if there were health potions?
  99. What was the last item you looked up on Google?
  100. What’s a cheesy joke you tell all the time?
  101. What’s the strangest wrong-number text or call you’ve ever received?
  102. What would keep you from accepting immortality if it came with a condition?
  103. What would be the most epic name you could choose if you could alter your first name?

Suggested questions to ask your boyfriend

  1. Where would you travel if you were to leave everything and go on a road trip?

This question is identical to the one above about “where would you live.” Rather than figuring out where your lover wants to settle down, you can figure out what kind of trip he enjoys.

It’s always better if you both enjoy the same things. It means more activities to do together and more topics to discuss.

  1. Would you rather be a queen or a happy spiritual person?

These days spirituality is gaining focus which means people are seeking calmness and enlightenment. According to where you stand, you can come to know if your man is the right match for you or not.

  1. What is something you tried your hardest to like but couldn’t?

You can figure out who forced him into liking the thing by looking at who he attempts to please. You can also tell how willing he is to confront that person or group. You’ll also learn more about his likes and dislikes.

  1. What was the finest aspect of your parents’ upbringing?

Family can be a difficult subject, yet learning about someone’s childhood can reveal a lot about them. Just remember to let him speak for himself, avoid making assumptions, and never criticise family members. When you criticise someone’s family, they become enraged.

  1. What makes you nervous?

Nervousness is a universal human characteristic. So, why don’t you find out what makes your guy feel uneasy? There’s a strong likelihood that speaking in front of a large gathering of people makes him uneasy, but if you can, urge him for more examples.

The bottom line

These questions are great for guiding the conversation and gaining insight into the type of person these guys are.

Because every guy is different, your results may vary with all of these questions to ask your lover. 

Some questions will spark the interest of some boyfriends while failing to catch the attention of others.

Choose the best according to your boyfriend.

About the Author

Sasha Aun
Sasha Aun
Hi, I am Sasha, a professional relationship expert, and a blogger. At Datinghelpguide, I write tips to create an attractive dating profile and guides on managing dating profiles on multiple apps.
×

Table of Contents