When we ask important questions, we want to accomplish more than just knowing something. We also want to arouse curiosity and tie our inquiries to what learners find interesting and relevant. We also want to encourage people to ask more detailed questions.

Because it is a discipline we apply every day, asking meaningful questions is the basis of learning and life. In fact, the majority of our success in life is determined by our ability to ask the right questions and make the right decisions.

If you want to know someone better then you are the one who needs to initiate a conversation with the right set of questions. To ease things for you, this article has 100 questions deeper enough to open up the person and know them. 

100 questions to get to know someone deeper

1. What three new habits do you want to adopt this year?
2. What comes to mind when you hear the word “future”?
3. Which of your childhood memories stands out the most to you?
4. What’s the one thing about yourself that you’d like to change?
5. Is it easier for you to be an introvert or an extrovert?
6. How harsh do you think you are?
7. Do you have any regrets in your life?
8. What are three things that you want to do before you die?
9. What piques your interest the most?
10. What do you think about while you’re alone?
11. What does “success” mean to you?
12. Do you aspire to be well-known?
13. What would you like to be remembered for?
14. What is the most important invention of our time?
15. What do you believe will be the final cause of humanity’s extinction?
16. Do you have a good time when you’re on social media?
17. What would the title of your life be if it were a novel, and why?
18. Have you ever been a witness to a miracle?
19. Is there any value in art in today’s society?
20. On a scale of one to ten, how satisfied are you with your life?
21. When was the last time a film brought you to tears?
22. What does “a life well lived” mean to you?
23. If you died today, what regrets would you have?
24. Is it possible for humans to avoid falling in love?
25. Is there such a thing as unrestricted liberty?
26. How did you get along with your parents as a kid?
27. What has been the most enjoyable period of your life thus far?
28. What were your feelings regarding school?
29. What was the most memorable trip you’ve ever taken?
30. Who was the first person you ever had a crush on?
31. What is the most significant chance you have squandered?
32. What was the length of your longest relationship?
33. What was the most defiant decision you ever made as a kid?
34. What has been the most significant change in your life since you were a child?
35. What was the craziest thing you’ve ever done?
36. What would your ideal metropolis look like if you were granted complete creative freedom?
37. Is it possible to achieve long-term peace?
38. Will you encourage your children and grandchildren to use social media?
39. Which circumstance is preferable: being broke or being alone?
40. Would you rather be alone or surrounded by people you know when you die?
41. What has been your lowest point this year?
42. What has been the happiest moment of your life this year?
43. Who is hiding behind the mask you wear in public?
44. Is your life heading in the right direction?
45. Are you willing to go above and beyond for something or someone?
46. Which comes out on top: reality or fantasy?
47. When was the last time you told your parents, “I love you?”
48. Who do you admire in life?
49. Do you give others advice, and if so, why?
50. Which is preferable: breaking hearts or being broken hearts?
51. Who would you choose to live with for a day if you could, and why?
52. What does your life mean to you?
53. What brings significance to your life?
54. What three wishes would you make if someone could grant them?
55. Are you willing to put your life on the line for someone, and if so, who?
56. What are the top five lessons you’ve had to learn the hard way?
57. Do you believe in science or magic?
58. How different would the world be if you hadn’t been born?
59. What does an ideal weekend look like to you?
60. Have you recently shattered someone’s heart?
61. Are you willing to move for the love of your life?
62. Do you keep a journal, and if so, how frequently do you update it?
63. Do you believe in giving cheating partners a second chance?
64. What is it about you that folks consistently misunderstand?
65. What would you say is the best way to describe your ideal vacation?
66. What are the two most important lessons you’ve taken away from a previous relationship?
67. What book or film impacted you the most, and how?
68. Are you a pushover or an assertive person?
69. In a romantic connection, what is your biggest turnoff?
70. Would you go to such lengths for a friend?
71. What are the realities or truths about which you are in denial?
72. Do you believe that the way you live your life makes a difference?
73. Why do you think you’d be willing to disclose your password with your romantic partner?
74. What are your thoughts on a cheating partner?
75. What age do you believe people should marry?
76. Why do you think you’ll make a good parent?
77. What would you do if your parents didn’t like your boyfriend or girlfriend?
78. Do you think persons of different sexes can be the best of friends?
79. Have you ever experienced the loss of someone close to you?
80. Who is the one person with whom you can discuss any topic?
81. Is your current career what you said you wanted to be as a child?
82. Do you think the present is truly superior to the past?
83. Would you consider relocating to a place where you have no relatives or friends?
84. What is a secret trait about yourself that you wish people were aware of?
85. What is your personal life philosophy?
86. Do you consider oneself to be religious or spiritual?
87. How would you define your life five years from now if all of your wants were granted today?
88. At your funeral, what will people say about you?
89. Do you believe in an afterlife, and if so, why?
90. Do you enjoy the person you’ve become?
91. When was the last time you burst out laughing?
92. Is it more important to have good looks or to have good brains?
93. What is your most traumatic elementary school memory?
94. Do you believe in tarot cards or fortune tellers?
95. What would it be if you could know one thing about your future right now?
96. Is there anything about the future that makes you nervous?
97. Have you ever made an important prediction about your future that came true?
98. Would you rather have a young body or a young mind until the end of your life?
99. What do you believe will be the most amazing invention made in your lifetime?
100. Do you believe we have the ability to modify our destiny, or do you believe it has already been written?

The bottom line

The only method to actually learn what lies beneath someone’s face is to ask them hard, intimate, and insightful questions. 

Furthermore, discovering a side of someone you may not have seen before can be a really enjoyable experience! 

Pick the best ones and share your experience.