When you’ve just met someone new, it is natural for you to want to know everything there is to know about this person. Most importantly, you want to know who they are as a person and if the two of you have anything in common and to see if you can imagine yourself being with them.

You’ll probably ask them some basic things and you’ll cover some of the typical conversation topics; you’ll want to know how they’ve spent their day and you’ll ask them to tell you more about their hobbies, education or career.

But the truth is that none of this will help you see the real them. If you want to know the essence of the person sitting next to you, you’ll have to think outside of the box and you’ll have to make your date a little bit different.

Because sadly, most of the initial conversation topics typical of the starting stage of a relationship are actually pretty shallow and are just small talk, without any follow-up questions. It’s like nobody even tries to get to the bottom of the other person and to get to know them for real.

A similar situation is with couples who have been together for a long time. You spend years of your life with a person but after a while, you get to the point where you ask yourself if you can say that you know your partner for real.

Yes, you know their habits and routines and you know some basic stuff about them but have the two of you ever tackled any deep topics or philosophical questions? Or have you been asking them the same types of questions for as long as you can remember?

So, here are 100 deep personal questions to ask a guy or girl you are just getting to know or to debate over with your life partner.

The truth is that talking about deep topics can be quite challenging but trust me—it will be worth it. You just have to pay attention and listen to their answer to every question if you want to make the best of this.

1. What was the last time you were truly happy?

2. Can you say you already had the love of your life?

3. Do you tend to stay friends with your exes?

4. How would your perfect day look?

5. If you could choose one person, alive or dead, to have lunch with, who would it be?

6. Who do you think has affected your life the most?

7. What was the saddest moment of your life?

8. What was the happiest moment of your life?

9. Which song really moves you?

10. If you could choose to spend the rest of your life in one place on earth, what place would it be?

11. Do you believe that two people can love one another for the rest of their lives?

12. Do you believe in the institution of marriage?

13. Are you religious and if so, what do you think is the purpose of human life?

14. What does spirituality represent to you and do you connect it with religion?

15. What are your biggest fears and insecurities?

16. What is your biggest regret?

17. If you could change one thing about yourself, what would it be?

18. Do you consider yourself an extrovert or an introvert and why?

19. If you knew you would die tomorrow, who would you want to call?

20. If you knew you only had a few days left to live, how would you spend them?

21. Where do you see yourself in ten years?

22. What would you like to tell your younger self?

23. If you had to choose between your career and love, which would you choose?

24. What would you wish for from a genie?

25. Do you hope that your future will be better than your present?

26. Is there someone or something you would sacrifice your life for?

27. What do you consider to be a healthy and mature relationship?

28. How long did your longest relationship last?

29. What do you think are your best qualities as a person?

30. What are your biggest personality flaws?

31. What do you have to offer in a relationship?

32. What do you look for in a relationship?

33. When was the last time you lied and what was it about?

34. Do you think there is something good in everyone?

35. Do you believe people can change?

36. Do you think you could change and what would it take for you to change some essential things about yourself?

37. What is the craziest thing you’ve done for the sake of love?

38. What is the most romantic thing you’ve done for a partner?

39. How would your perfect life look?

40. Do you want children?

41. How would you like to raise your children, if you want to have any?

42. Did you become the person you wanted to become when you grew up?

43. Do you think you could forgive a person who cheated on you with someone else?

44. Why do you think people cheat?

45. Do you think that you are a fighter or a quitter?

46. What do you usually do to cheer yourself up when you are in a bad mood?

47. What are your biggest concerns in life?

48. Have you ever broken someone’s heart?

49. Have you ever had your heart broken?

50. What are you most grateful for?

51. Who would you say was guilty for your last break-up?

52. Does your career make you happy and do you see yourself doing this job for the rest of your working years?

53. Which qualities do you look for in a person?

54. What was the most important lesson your parents taught you?

55. What movie affected you the most?

56. Is there a celebrity you identify with?

57. What are you most proud of in life?

58. Who are the three people you love the most?

59. What is the most exciting thing that has ever happened to you?

60. What was your favorite school subject and why?

61. Can you remember a teacher who impacted you the most?

62. If you had to choose between having an attractive partner and having a partner with a nice personality, which would you choose?

63. Have you ever done something illegal and if so, what was it?

64. What do you honestly think about drugs?

65. What is your favorite book and why?

66. If you had the ability to change one thing from your past, what would it be?

67. If you could trade your life with someone else, who would it be with?

68. Do you think we create our own happiness or are we impacted by life circumstances?

69. Do you usually follow your heart or your mind?

70. Does there exist a person in your life who knows all of your deepest secrets?

 

71. How many real friends do you have?

72. What is your biggest failure in life so far?

73. What is your biggest success in life so far?

74. Do you believe in love?

75. When was the last time you cried and why?

76. What is the first thing that goes through your mind when you remember your childhood?

77. What do you think is the biggest difference between men and women?

78. What would be the first thing you would do if you could spend one day as a person of the opposite sex?

79. What is your biggest weakness?

80. What is your biggest strength?

81. What are your biggest deal-breakers in a new relationship?

82. If you had one day to spend a million dollars, how would you spend it and what would be the first thing you would buy?

83. What do you do when you have trouble sleeping?

84. What is your life motto?

85. How do you think the people closest to you would describe you in a few sentences?

86. Would you rather live a boring life for a hundred years or an exciting one for half of that time?

87. If you could pick one person to ask anything in the world and they would have to answer you honestly, who would that person be and what would you ask them?

88. What was the thing that caused you the most emotional pain so far?

89. What is the most memorable lesson you’ve learned from the opposite sex?

90. What was the best day of your life so far?

91. What would you sacrifice for the sake of money?

92. What is the one thing that you can’t imagine living without?

93. Who is the one person you can’t imagine living without?

94. What moves you the most?

95. How many people do you trust completely?

96. What is your biggest accomplishment in life?

97. What do you think is the first impression people have about you when they meet you?

98. What activity relaxes you the most?

99. What was the last thing you dreamed about?

100. What is the one thing you want to do before you die?