101 Thoughtful and Provoking Questions To Ask To Get To Know Someone

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Excerpt: Looking for questions to ask to get to know someone? This list has you covered. Good for getting to know someone new or old, known or unknown, stranger or friend. Questions are the key to meaningful connection. Enjoy.

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Introduction: Questions Are The Key

I am semi-obsessed with questions. I think that questions are the ultimate mind hack. I think questions can help direct focus and productivity. I think questions can help you find your life path. I think that the people who ask the best questions are the ones who get the best answers and resultantly, get the best results in life. And, of course, I think that questions are the key to meaningful conversation and deeper connections—something we all crave and instinctually desire.

For, how better to get to know someone than by asking them better questions? Questions that get them to share who they are, what they think, how they feel, that go beyond the normal inquisition, and get them to express all that is going on inside of them that’s hidden from the naked eye? There are, as far as I can tell, but two ways to get to know a person for who they are on the inside—either by waiting and letting them express it themselves or by asking them the question(s) that get them to reveal the part of their insides that the question begets.

You can sit and wait, but I fear what you might find is more people hiding than spontaneously sharing. Which leaves your prompting. Questions are the secret. They are the key. They are the bread and butter of every good conversation. The only real question is, will you have the courage to ask? And, I suppose this is a real question, too, what will you ask when the opportunity is there? Enter our list of 101 thoughtful and provoking questions to ask to get to know someone.

I compiled for you below, 101 of the most amazing questions I could think of and find that would help prompt much more than a one or two word answer in reply. In fact, that’s really the key to all good questions—they’re framed in a way that allows space for explanation, elaboration, description, intrigue, challenge, and reflection. What’s even more interesting about this whole process, is that while the questions may remain the same, the answers will almost always differ—even when asked to the same person. For, we are not a stagnant, unchanging organisms. We are very much alive and constantly evolving, learning, changing, and experiencing new things.

So, this is not a list that is to be explored and marked as being completed. Rather, it’s a list that can be enjoyed today and enjoyed again tomorrow. These are questions that can be shared with a friend, with a lover, with a stranger, and back again with the same person again in the future. And, of course, there’s no format. You can answer only the ones that appeal to you. You can challenge yourself and/or the person you’re sharing this list with to answer all of them with you. Or you can pick randomly!

Enjoy this list how you may. My hope, is that it will prompt dialog that goes much further than the usual exchange. We are so much more than one or two word answers. We are divine and infinitely complex being on the inside and conversation helps us unravel and make sense of that complexity. Let’s dive a little deeper into each other’s minds and unravel together. Let’s share some of our uniquenesses, insights, and vulnerabilities. Let’s go beyond the superficial and make some space for more of what’s real. Let’s start connecting more and hiding less. And, perhaps most importantly, let’s be the one who asks the first question. Good luck.

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101 Thoughtful and Provoking Questions to Ask To Get To Know Someone

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1. How are you, really?
2. What is your perfect day?
3. What makes you nervous?
4. What’s your claim to fame?
5. Is there a feeling you miss?
6. What would you rate 10/10?
7. What do you crave more of?
8. What risks are worth taking?
9. What keeps you up at night?
10. What is your guilty pleasure?
11. What lie do you tell most often?
12. Has anyone ever saved your life?
13. What is a dream you’ve let go of?
14. What do you hope never changes?
15. What’s your favorite season? Why?
16. What do you do to deal with stress?
17. How often do you stay up past 3am?
18. What takes up too much of your time?
19. What do you think is weird about you?
20. Has a stranger ever changed your life?
21. What’s the last adventure you went on?
22. What would your last meal on earth be?
23. What’s your favorite way to waste time?
24. What smell brings back great memories?
25. Are you lying to yourself about anything?
26. What do you want to be remembered for?
27. What are you absolutely determined to do?
28. What three words best describe you? Why?
29. What is something you will NEVER do again?
30. What are you still trying to prove to yourself?
31. How do you think traveling changes a person?
32. What restaurant do you eat at the most? Why?
33. Who in your life brings you the most joy? Why?
34. When was the last time you surprised yourself?
35. What is something that you are obsessed with?
36. What do you think of tattoos? Do you have any?
37. What’s worth spending more on to get the best?
38. What is the strangest dream you have ever had?
39. Which of your scars has the best story behind it?
40. What are some goals you have already achieved?
41. What’s the furthest you’ve ever been from home?
42. Where do you usually go when you have time off?
43. What do you spend the most time thinking about?
44. What title would you give this chapter of your life?
45. What have you created that you’re most proud of?
46. What do you think your Instagram says about you?
47. What’s been your happiest memory this past year?
48. What are the three best apps on your phone? Why?
49. What mystery do you wish you knew the answer to?
50. What life lesson took you longest to learn? Unlearn?
51. What is the most annoying habit someone can have?
52. What are you more afraid of, failure or success? Why?
53. What’s the most spontaneous thing you’ve ever done?
54. What has been your earliest recollection of happiness?
55. What are the three most important things in life to you?
56. What’s something you like to do the old fashioned way?
57. Who is your longest standing friend? How did you meet?
58. Are there any songs that always bring a tear to your eye?
59. What part of your life works? What part of your life hurts?
60. Do you usually achieve the goals you set? Why or why not?
61. Was there ever an event in your life that defied explanation?
62. When people look at you, what do you think they see/ think?
63. If you opened a business, what kind of business would it be?
64. What challenging thing are you working through these days?
65. If you were the only human left on earth, what would you do?
66. What are some of your personal “rules” that you never break?
67. What are some events in your life that made you who you are?
68. What is a compliment you wish you received more frequently?
69. What’s the most pain you’ve ever been in that wasn’t physical?
70. Have you ever saved an animals life? How about a person’s life?
71. What do you regret not doing/ starting when you were younger?
72. What is something you wouldn’t want to change about yourself?
73. How would you describe the feeling of being in love in one word?
74. What would you do if you knew you were going to die in one day?
75. What is the craziest, most outrageous thing you want to achieve?
76. If you didn’t have to sleep, what would you do with the extra time?
77. What’s the most unexplainable thing that’s ever happened to you?
78. Who has had the biggest impact on the person you have become?
79. What question are you trying to answer most in your life right now?
80. What has been the best compliment a stranger has ever given you?
81. Time freezes for everyone but you for one day. What would you do?
82. What do you do to improve your mood when you are in a bad mood?
83. If you have, when was the moment you realized you weren’t invincible?
84. How much time do you spend on the internet? What do you usually do?
85. Have you ever told someone, “I love you,” but didn’t mean it? If so, why?
86. When people come to you for help, what do they usually want help with?
87. if you could make one rule that everyone had to follow, what would it be?
88. If you could have a video of any one event in your life, what would it be? Why?
89. Which app has helped society the most? Which one has hurt society the most?
90. What could you give a 40 minute presentation on with absolutely no preparation?
91. What’s something about you that others would never guess just by looking at you?
92. What does your own personal hell look like? How about your own personal heaven?
93. Do you think the image you have of yourself matches the image people see you as?
94. If you could get to know someone in your life on a deeper level, who would it be and why?
95. Who would be the worst person to be stuck in an elevator with? Who would be the best person?
96. If you could call up anyone in the world and have a one-hour conversation, who would it be and why?
97. What do you think is the most strange or unfamiliar thing about you from other people’s perspectives?
98. How should success be measured? And by that measurement, who is the most successful person you know?
99. If you could have it your way: who would you be with? Where would you be? And what would you be doing?
100. Would you rather leave your hometown and never be able to return again, or stay in your hometown but never be able to leave?
101. Imagine you are at the end of your life and you are granted the ability to repeat one day. Which period of your life do you choose to repeat?

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