100+ Deep Questions to Ask a Guy to Get Him to Open Up

It can be difficult to figure out just what to say to a person in order to deepen your bond if you want to get to know him better. 

Guys are easy to impress but some of them (the ones you pick) can be a bit difficult. So, here are 100+ deep questions to ask a guy to get him to open up.

Questions to ask a guy to get to him to open up

  1. What is your favourite sport?
  2. What do you love to do in your leisure time?
  3. When was the last time you cried?
  4. What hurts you the most?
  5. Have you ever talked abot your feelings?
  6. What kind of girls you like?
  7. Who is that one person you can call as your crying shoulder?
  8. What is your biggest regret?
  9. When you are happy what you love to do?
  10. Do you know how to respond to a compliment? Or
  11. How do you usually respond to a compliment? 
  12. Do you celebrate your birthday? If not, why?
  13. Are you a listener or a speaker?
  14. Do you like memes? Which one is your favourit?
  15. Do you like dark jokes or are you a pun lover?
  16. Do you support LGBTQ?
  17. Do you have any friend who is not straight?
  18. Did you ever think of dating a girl?
  19. What is your zodiac sign?
  20. Do you practice mindfulness?
  21. What kind of people are your pick?
  22. What is your biggest flaw?
  23. Do you want to get married someday?
  24. What are your thoughts on Pink Floyd?
  25. What kind of dancing do you prefer?
  26. What’s your favourite record?
  27. What was the worst thing you’ve ever experienced?
  28. How many times have you went on a date with a random person?
  29. Have you ever been in love?
  30. What was your proudest accomplishment?
  31. Do you enjoy being around animals?
  32. What was your favourite music when you were a teenager?
  33. What makes you ecstatic?
  34. If you could possess a planet, would you call yourself a god?
  35. Have you heard about the oldest library that was set on fire?
  36. Is happiness a myth?
  37. Do you think we are all like a robot made by aliens?
  38.  As a kid, what were your thoughts about the world?
  39.  What do you think you should have done differently in your life?
  40. What are your thoughts on large parties versus tiny house parties?
  41. What age do you think is the most enjoyable in your life?
  42. What age do you consider to be the most difficult in your life?
  43. What are the top three things you want to do before you die?
  44. So far, what has been your proudest achievement?
  45. What is one thing you wish you could do but know you’ll never be able to?
  46. What is it that you are most scared of?
  47. What is the most daring thing you’ve ever done?
  48. Tell me about the wisest piece of advice you’ve ever received.
  49. When are you the happiest?
  50. What has been your craziest dream recently?
  51. What is your all-time favourite book?
  52. What is the total number of countries you have visited?
  53. What was the designation of your first job?
  54. What is your current job title and how long have you been there?
  55. Are you a person who thrives on competition?
  56. What is one of your favourite words?
  57. What is it that keeps you up at night?
  58. What is your ideal automobile?
  59. What is the title of your favourite book?
  60. What is the most dreadful film you’ve ever seen?
  61. Which superpower would you most like to have?
  62. What is the most enjoyable activity you’ve ever shared with your friends?
  63. Do you have a stronger bond with your mother or father?
  64. Which member of your family is your favourite?
  65. What do you consider to be your most outstanding accomplishment?
  66. What’s the strangest habit you have?
  67. What is your most terrifying fear?
  68. What’s your go-to phrase when you’re in a hurry?
  69. What’s one foolish, childish item you still keep stashed away in your room?
  70. Who has had a significant impact on your life?
  71. Who helped you grow into the person you are today?
  72. What is one thing you wish to accomplish before you pass away?
  73. What abusive word you use the most? And why?
  74. What would you say is the definition of ‘love’?
  75. Have you had your heart broken before?
  76. What is one thing you’ve discovered about yourself as a result of a previous relationship?
  77. What is your most vexing pet peeve?
  78. What is one thing that completely turns you off?
  79. What is one thing that completely turns you on?
  80. What would you alter if you could redo your history?
  81. What do you consider to be your most attractive physical feature?
  82. What is one aspect of your personality that you find appealing?
  83. Who or what is your go-to person or activity when you’re feeling down?
  84. What would you eat if you could only eat one food for the rest of your life?
  85. What is one thing about which you are extremely enthusiastic?
  86. What three words would you use to describe yourself if you had to?
  87. What is the most interesting place you’ve ever visited or travelled to?
  88. Which alcoholic beverage is your go-to?
  89. What kind of first date would you go on?
  90. What three wishes would you make if you had the opportunity?
  91. What would you do if you had a full day without any duties or responsibilities, a day to do whatever you wanted?
  92. What’s the most flattering praise you’ve ever gotten?
  93. What is one thing about you that others would never guess just by looking at you?
  94. What is it about the other sex that you find appealing?
  95. What are the top three attributes you look for on a date?
  96. What do you think is the sweetest thing you’ve ever done for a girl?
  97. What would others say about you if I approach them?
  98. Which of your five senses would you give up if you had to lose one, and why?
  99. What is the most physically demanding thing you’ve ever done?
  100. Have you ever made a decision that completely transformed your life? If yes, what was it?
  101. What are your favourite weekend activities?
  102. What is your horoscope sign? And do you believe it applies to you?
  103. What is your greatest remorse?
  104. What can always bring a smile on your face?
  105. What’s your favourite junk food, drink, or snack?
  106. Which two fast food restaurants would you choose if you had to eat fast food every meal?
  107. What is the most mentally challenging thing you’ve ever done or experienced?
  108. What is the most enjoyable aspect of your job?
  109. .What is one characteristic that characterises you?
  110.  What would you do in your last 24 hours if tomorrow was your last day on Earth?
  111. Have you ever taken part in a protest?
  112. Would you go out with two different girls on the same day?
  113. Would you ever date a deafeningly deafeningly deafeningly de
  114. Please tell me about the one who escaped.
  115. What is the total number of pairs of shoes you own?
  116. What is you favourite food and beverage?
  117. Which sports car you love?
  118. Do you watch football?
  119. Do you watch F1 race?
  120. Do you love X-trials? If yes, who’s your favourite?
  121. Dhoni, Ronaldo, Messi or Toni, who would you choose to take a picture with?

Suggested question to ask him

  1. What is it about your job that you enjoy the most?

Asking this work-related question will not only bring you closer together by exposing more about his daily life, but it will also show his priorities. This can assist you to uncover what he’s most enthusiastic about in his work, regardless of what element of the job he enjoys the most.

  1. Where Would You Go If You Could Travel Anywhere?

Travel questions are not only a terrific way to start a pleasant conversation, but they may also lead to a couple’s getaway down the future.

  1. What Kind of Relationship Do You Want?

This is a crucial question to ask a guy in order to determine whether you and he are on the same page. If you want a serious relationship but he’s only interested in friends with benefits, it’s not a good match.

  1. What is your all-time favourite film?

Is he a lover of action movies? Horror? Drama? Knowing what kinds of movies he enjoys will help you learn more about his interests and passions while also assisting you in planning future movie dates.

  1. What is something that just a few people are aware of about you?

This inquiry can help you learn something about your partner that he only shares with the individuals that matter to him.

  1. What does a perfect date mean to you?

This is a fantastic method to learn about his interests while also offering you ideas for a future date!

  1. What is it that you are most afraid of?

Inquiring into his anxieties might be a fascinating technique to get to know him better if you want to understand more about him than the surface.

  1. What’s the best present you’ve ever gotten?

This inquiry is a terrific technique to learn more about what your boyfriend finds meaningful and notable if you want to know what he actually values.

  1. What are some of the things on your bucket list?

Is he hoping to go skydiving, travel to Greece, or win the Pulitzer Prize? A query about his bucket list is a fun way to discover more about what he hopes to achieve in the future and if you and he have similar aspirations.

Summing up

These are wonderful questions to ask while you’re still getting to know someone, such as if you’re on your first, second, or third date with a boy and want to learn more about him. 

They’re also good to remember even if you’ve been dating for a while and aren’t sure what to chat about over dinner. 

You’ll learn more about each other and potentially be able to have more personal conversations. Some of the questions are lighthearted and playful, while others are deep and unpredictable.

Use these and share your experience.

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.
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