These deep personal questions are designed to get to know a person you’re interested in, to find more information that will help you get close to them and try to sweep them off their feet.

If your questions are good and interesting, you can really capture a person’s attention, which will definitely get you to the answers you want to hear.

These types of questions don’t have to be used only when you’re interested romantically in someone, you can also use them when you are new to a group and you want to fit in.

Sure, these questions are not something you can’t live without but wouldn’t it be nice to have an ice-breaker line when you meet someone new or when you’re in an awkward situation and you want to save the day by breaking an awkward silence.

Deep personal questions to ask a guy:

100 Deep Personal Questions To Ask A Guy And A Girl

1. What do you think about online dating and would you ever try something like that?

2. Would you make a bucket list and try to complete it within a year?

3. What’s your ideal weekend?

4. Since we’re sharing things, what’s the craziest thing you’ve ever done?

5. What’s your relationship deal-breaker and is there something you just can’t stand?

6. Have you ever lost someone close to you?

7. Off the top of your head without too much thinking, what’s your biggest regret in life?

8. Do you have a person in your life you can talk to?

9. What’s your opinion about online dating on Tinder?

10. What phase in your life do you think you are at right now?

11. What’s your idea of a perfect life?

12. I’m a big, old bookworm—do you have a favorite book or movie?

13. If you could choose a location anywhere in the world to go for a vacation, where would it be and what’s your idea of a perfect vacation?

14. Are you happy with yourself, or is there something you would like to change, something that you’re not proud of?

15. Do you like the way you look?

16. How much time do you spend getting ready before going out? And be honest!

17. Do you believe in God or in any kind of a higher force or do you think that there is nothing out there?

18. What do you think about where we go when we die and is there something more, or is this it?

19. Is your personality extrovertive or introvertive?

20. Have you ever dated a crazy chick?

21. What’s the worst thing a girlfriend did to you?

22. What’s the best thing that happened to you in life?

23. What’s the worst thing that happened to you in life?

24. Where do you see yourself 10 years from now?

25. What does the word success mean to you?

26. What does the word love mean to you?

27. What’s the most romantic thing you’ve ever done for a girl and how did she react?

28. Are looks more important to you than brains?

29. Are you a boob or a butt guy?

30. What do you think—can enemies be friends?

31. Can men and women be friends without sexual tension between them?

32. Have you ever cheated on someone?

33. How would you react if someone cheated on you, would you forgive them and why?

34. Would you raise your kid exactly like your parents raised you, or would you do something different, and if the answer to the latter is yes, what would it be?

35. Do you stay in contact with your exes?

36. Do you lose your temper easily?

37. If you fell in love and that person had to move to another country, would you follow her?

38. Is it easier for you to sometimes put your thoughts down on paper and do you feel better afterward?

39. Do you think life gives you second chances?

40. Would you ever stay in a toxic relationship?

41. What is the thing that makes you the most nervous?

42. Are you an adrenaline junkie?

43. Do you like music?

44. What three words would you use to describe your best friend?

45. Do you have a pet?

46. Do you like being single?

47. What’s your biggest fear?

48. Can you name the three most important people in your life?

49. Who is your role model, who do you look up to?

50. Where do you go when you want to be alone?

51. What’s your favorite beer?

52. What was your craziest drinking experience?

53. If you could change one thing to make the world a better place, what would it be?

54. What’s your favorite sport to watch and to play?

55. What’s your favorite meal?

56. On a scale of 1 to 10, how weird are you?

57. NSYNC or Backstreet Boys?

58. How good of a person are you on a scale of 1 to 10?

59. What’s your dream job?

60. What’s your favorite food?

61. Are you a dog or a cat person?

62. What’s the closest you’ve ever come to being arrested?

63. If you were to catch a goldfish, which three wishes would you have?

64. Who’s your favorite Marvel character and why?

65. Do you believe in destiny?

66. If you had the ability to travel through time, to which period would you go and why?

67. If you could, what would you change about your past?

68. If you had a task to ask a person just one question, what would it be?

69. What are your priorities in life?

70. Money or love?

71. What’s your favorite female body part?

72. How many times have you been in love?

73. When you are in a bad mood, do you prefer whether someone tries to cheer you up or leaves you alone?

74. What is the one question you will never give me an answer to?

75. What advice would you give to the younger version of yourself?

76. Do you want to have kids?

77. Would you ever forgive yourself for doing a girl wrong?

78. Would you ever hide your girlfriend from your friends?

79. What is the one thing you’re the most insecure about?

80. Do you think you’re going to be a good parent?

81. Do you keep a journal?

82. Are you musical?

83. Are you into politics?

84. What’s the weirdest conversation you’ve ever had with someone?

85. What’s your favorite movie scene?

86. What’s your perfect date outfit?

87. When did you lose your virginity?

88. What’s your middle name?

89. Is there something about your life that you just keep ignoring because you aren’t ready to face it?

90. What’s the one thing that can always bring a smile to your face?

91. What is the one thing you can’t live without?

92. What’s the biggest decision you ever had to make?

93. What was the most stressful moment of your life?

94. Would you ever break the law?

95. What’s the most inspiring thing you saw someone do?

96. What empowers you?

97. Have you ever been depressed?

98. Do you believe in heaven and hell?

99. Are you a workaholic?

100. Would you ever put your life in someone else’s hands and if you would, who would that person be?

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