100 questions to ask people

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13-09-2025

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100 Questions to Ask People: Spark Engaging Conversations and Deepen Connections

This extensive list of 100 questions is designed to spark engaging conversations and help you deepen connections with others. We've categorized the questions for easier navigation, ranging from lighthearted and fun to more profound and introspective. Use these questions to break the ice, learn more about someone, or simply foster a richer, more meaningful conversation.

I. Getting to Know You: Lighthearted & Fun

1. What's your favorite way to spend a lazy Sunday?
2. What's the most embarrassing song you secretly love?
3. If you could have any superpower, what would it be and why?
4. What's the most ridiculous thing you've ever done?
5. What's your go-to karaoke song?
6. What's the funniest movie you've ever seen?
7. What's your favorite childhood memory?
8. What's the weirdest food combination you enjoy?
9. What's one thing you're really good at?
10. What's your favorite animal and why?
11. What's your favorite season and what do you love about it?
12. What's your favorite type of weather?
13. If you could travel anywhere in the world, where would you go?
14. What's your favorite holiday tradition?
15. What's the most spontaneous thing you've ever done?
16. What's your favorite board game or card game?
17. What's your favorite type of music?
18. What's your favorite way to relax?
19. What's the best concert you've ever been to?
20. What's a skill you'd like to learn?

II. Exploring Interests & Passions:

21. What are you passionate about?
22. What's a hobby you're currently pursuing?
23. What's a book that has impacted you?
24. What's a movie or TV show that you've recently enjoyed?
25. What's a cause you care deeply about?
26. What's something you're proud of accomplishing?
27. What's your favorite thing about your job (or what you do)?
28. What's a skill you wish you were better at?
29. What are you currently learning or studying?
30. What's a dream you're working towards?
31. What's a place you'd love to live?
32. What's your favorite historical period?
33. What's a subject you're fascinated by?
34. What's your favorite type of art?
35. What kind of music inspires you?

III. Deeper Conversations & Self-Reflection:

36. What's your biggest fear?
37. What's your biggest regret?
38. What's something you're grateful for?
39. What's a lesson you've learned the hard way?
40. What's a quality you admire in others?
41. What's a quality you're working on improving in yourself?
42. What's your definition of success?
43. What's your personal philosophy on life?
44. What's something you're struggling with right now?
45. What makes you feel truly alive?
46. What's a moment in your life that changed you?
47. What's something you're proud of overcoming?
48. What's your biggest accomplishment?
49. What's a goal you hope to achieve in the next year?
50. What's your biggest strength?

IV. Opinions & Beliefs:

51. What's your opinion on [current event]?
52. What's your political viewpoint?
53. What's your stance on [social issue]?
54. What's something you believe strongly in?
55. What's a belief you've changed your mind about?
56. What's a common misconception about you?
57. What's a stereotype you'd like to break?
58. What's a topic you're passionate about debating?
59. What's your opinion on technology's impact on society?
60. What's your view on the future?

V. Relationships & Connections:

61. What's your favorite thing about your family?
62. What's your favorite thing about your friends?
63. What's the best piece of advice you've ever received?
64. Who's someone who inspires you?
65. What kind of relationship do you value most?
66. How do you maintain healthy relationships?
67. What's the most important quality in a friend?
68. What do you look for in a romantic partner?
69. How do you define love?
70. What are you most thankful for in your life?

VI. Dreams & Aspirations:

71. What's your ideal career?
72. What kind of impact do you want to make on the world?
73. What's your definition of happiness?
74. What does your perfect day look like?
75. What's something you've always wanted to do but haven't yet?
76. What are you most excited about for the future?
77. What are some things you want to accomplish before you die?
78. What legacy do you want to leave behind?
79. What's something you're working towards that might seem impossible?
80. What's a skill you'd like to master?

VII. Creative & Imaginative:

81. If you could live in any fictional world, which would it be?
82. If you could invent anything, what would it be?
83. If you could have dinner with any three people (living or dead), who would they be?
84. If you could time travel, where would you go?
85. If you were a superhero, what would your name and powers be?
86. If you could change one thing about the world, what would it be?
87. If you were stranded on a desert island, what three things would you take with you?
88. What would be the title of your autobiography?
89. Describe yourself in three words.
90. If your life were a movie, what genre would it be?

VIII. Fun & Quirky:

91. What's your favorite joke?
92. What's the weirdest dream you've ever had?
93. What's your favorite quote?
94. What's your guilty pleasure?
95. What's the most unusual talent you have?
96. What's something you collect?
97. What's your favorite scent?
98. What's your spirit animal?
99. If you could only eat one food for the rest of your life, what would it be?
100. What's a fun fact about yourself?

Remember to tailor the questions to the context of your conversation and your relationship with the person you're speaking with. Listen actively to their responses and engage in thoughtful follow-up questions to create a genuine and meaningful connection.