Do you want to find out more information about someone, but you don’t want to be overly intrusive? If you have questions you seek answers to, and you don’t want to influence their answer or make them feel as if you’re pressuring them, you should ask them open-ended questions. 

Open-ended questions can be an incredible tool when you are trying to uncover more about someone you want to get to know. However, not many people truly understand the art of open-ended questioning or what it even is. 

When you ask an open-ended question, you prompt the beginning of a conversation that isn’t going to end abruptly. If you want to engage in a lengthy discussion, you need to avoid closed-ended questions that begin with “what if,” “why,” and “how.” Questions that start with these words can end with single-word answers like “yes” and “no.” 

Close-ended and open-ended questions have their place in various conversations in our daily lives, but it’s essential to establish which situation requires open-ended questioning. Essentially when you’re getting to know someone, whether it be for work purposes, dating purposes, or friendship purposes, you need to lead your conversation with open-ended questions. 

To help you understand what constitutes open-ended questions, we have compiled a list of the 101 best open-ended questions we think will help you in a variety of different situations. 

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The 101 Best Open-Ended Questions of All Time

1. What are your plans for today?
2. Could you tell me what you are thinking about?
3. How did you complete this task so well?
4. What do you believe constitutes having a good life?
5. Can you tell me how to make your favorite dinner dish?
6. Why do you like the music that you do?
7. What are the main strategies you employ when making monumental decisions?
8. What policies do you believe governmental institutions could implement to improve people’s lives?
9. Can you tell me some of the plans you have for your future?
10. Do you have a specific person in your life who has influenced how you go about life?
11. Could you tell me about something that you have done in your life that you are proud of?
12. What is the one moment that you wish you could take back?
13. Are there any social constraints that you despise?
14. What are your thoughts on the education system?
15. Are you facing any challenges in life?
16. What was your favorite subject in school, and why was it your favorite subject?
17. What are the various ways you can solve the current problems in your life?
18. If you were a teacher, what subject would you teach, and how would you teach your students?
19. What are your current dreams?
20. Is there a particular profession you wanted to pursue as a child, and why did you want to pursue it?
21. Why do you believe that happiness is easily achieved by some but hard to attain by others?
22. How do you think humankind will fight future wars?
23. Can you explain a few of the life hacks that you have found to help you?
24.  If you could invent a television show, what genre would it be, and what would it address?
25. Why do you think people react to the same situation differently?
26. How would you explain your country’s justice system to an extraterrestrial being?
27. How do you think society’s standards of beauty have changed during your lifetime?
28. How would you define love?
29. What is your biggest motivation to succeed in life, and why is it your biggest motivation?
30. What rules do you have that govern how you live your life?
31. How did you discover what you are passionate about in life?
32. What do you find to be your most annoying habit, and why?
33. What do you like to do when you are not working, sleeping, or eating?
34. How do you think your country would change if those under 18 were allowed to vote during presidential elections?
35. What is the very best story you have from the time when you were in high school or university?
36. What do you consider the best part of your day and why?
37. What rules do you want to break at your school or place of work?
38. Do you believe that professors and their students should be allowed to have relationships and if not, why not?
39. Do you think most punishments fit their crimes, and if not, why not?
40. How would you explain your life to a complete stranger you just met at an event?
41. Can you explain the various personality traits that you are seeking in a partner?
42. What is your most controversial opinion, and what is your reasoning for it?
43. Why do you think humankind builds monumental structures?
44. What are the most valuable lessons you feel humankind needs to learn from events of the past?
45. Do you think your values differ from the majority of people, and how do they differ?
46. What is the one thing you would instantly change about your country to make it better, and how can someone change that aspect?
47. Why do you think it’s so challenging to learn from the mistakes we make?
48. What is the very first and last thing you notice about someone when you first meet them, and why do you think you notice that thing first?
49. What are the things that attract you to a person romantically?
50. Why is it important for people to have free will? 
51. Why should religion be allowed to exist?
52. Why do you believe governments should continue governing? 
53. What are a few of the best pickup lines you were ever told on a night out?
54. What are your favorite games, and why do you enjoy playing them?
55. What was your favorite storybook as a child, and how has it influenced your life?
56. Why do you feel animals can understand us?
57. Why do you like to spend so much time alone?
58. What are the things in life that you are most grateful for having?
59. How would you describe your appearance to me?
60. What do you think you would be famous for, and why do you think you would be famous for it?
61. What do you believe is the recipe for succeeding in life and achieving one’s hopes and dreams?
62. Why are your family members inspiring?
63. Can you list the 10 best places you have visited and why they have made your top 10 list?
64. Who is currently your favorite social media influencer, and why do they matter to you?
65. Can you describe the ideal man or woman?
66. If you could start any baseless conspiracy theory, what would it be, and do you think people would believe it, and why would they believe it?
67. Why is makeup a deceptive tool, and do you think it is harmful to society?
68. How would you change sporting events to make them more enjoyable for everyone?
69. Why are routines imperative to success?
70. What are the most significant life events you have lived through, and how have they changed you?
71. In your opinion, what does the media do well at, and what do they do poorly at?
72. How would you manage your family during an environmental crisis?
73. What is the place you find yourself visiting often and why?
74. What are the traits you find to be the most destructive in a person, and why?
75. How would you define yourself, your dreams, your goals, and your aspirations in life?
76. How do you choose to spend your Sundays, and what do you look forward to most on the weekend?
77. Can you explain your worst nightmare in detail?
78. Can you explain the moments in life when you were happiest?
79. Do you believe money can honestly buy happiness, and if so, why?
80. How are you going to make your dreams come true in life?
81. Can you tell me three of the best jokes you know right now?
82. Could you describe the home you grew up in and your favorite memory from living in that home?
83. How do you go about making yourself face your worst fears and how do you make yourself live without regrets?
84. Why shouldn’t people live in the past and instead look to the future?
85. Can you explain your most prized possession and why it’s important to you?
86. What is the true story behind how you met your husband or wife?
87. Why do you think people enjoy listening to music or watching movies that upset them or make them sad?
88. Can you explain the most important parts of your favorite movie or novel?
89. How exactly would you prepare if you found out a zombie apocalypse or other dystopian event was imminent?
90. What types of people would you take with you if you were creating a colony on Mars?
91. How do you think humankind would react if the internet went offline and never started back up?
92. How do you think people would react if it were uncovered that the supernatural exists?
93. What do you think makes someone a hero?
94. How would the world change if men could suddenly hear women’s thoughts?
95. Why do you think the current generation of people is different from your generation?
96. Can you explain what would feature in a playground created for adults?
97. Do you feel the cost of technology is too dear to pay?
98. How do you think television shows will be in 20 years?
99. How would you introduce someone to everyday life if they had been in a frozen sleep for 200 years?
100. What do you believe are the limitations of capitalism, and do you feel democracy is a better political system?
101. How do you react to stress, and do you have any coping mechanisms? 

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