There’s something so underrated about a great question.
Not the surface-level stuff.
I mean the kind of questions that cause someone stop and think. The kind that spark completely new thoughts.
I put this list of questions to get to know someone together because I’m tired of hearing people say they want a deeper connection… while recycling the same three boring questions that never go anywhere.
(I’m looking directly at you, single people who think it’s a swell idea to plop down on a first date and immediately ask, “why are you single?”)
Anyway…
If you want to really get to know someone, you need to ask better questions and listen more.
These questions to ask aren’t clinical or overly scripted.
They’re thoughtful, open-ended, and flexible enough to use with anyone— friends, new connections, longtime partners, or someone you just met in the airport security line.
Some of these are light. Some go deep.
All of them are designed to help you actually connect.
Here are 101 of the best secret-weapon questions to get to know someone:
Personal Growth & Self-Discovery
1. What’s a dream you’ve tucked away for the moment?
2. What’s one value you wish more people lived by?
3. What’s a lesson you had to learn the hard way?
4. What’s something you’re proud of that most people don’t know about?
5. What belief have you outgrown?
6. What’s a fear you’re learning to let go of?
7. What’s a truth you wish everyone knew?
8. What’s something you’re currently working on within yourself?
9. What’s one thing you’ve never said out loud but think about often?
10. What’s something you secretly wish people would notice about you?
11. How do you know when you’re growing?
12. What’s one thing you’re actively trying to unlearn?
13. What’s something you’ve changed your mind about recently?
14. What’s one risk you’re glad you took?
15. What’s something you used to be afraid of that no longer scares you?
16. How do you define success for yourself?
17. What’s a moment that changed your perspective?
18. What’s something you’re learning to forgive?
19. What’s one way you’ve changed for the better in the last year?
20. What’s a habit or routine that brings you joy?
Relationships & Emotional Intimacy
21. How do you know when you’re in love?
22. What’s something that makes you feel truly understood?
23. What does emotional intimacy mean to you?
24. What’s your relationship to silence?
25. How do you process big emotions?
26. How do you like to be comforted when you’re upset?
27. How do you express affection?
28. What’s the most thoughtful thing someone has done for you?
29. How do you define emotional safety?
30. What does “home” mean to you?
31. How do you show affection?
32. What brings you a sense of peace?
33. What does vulnerability mean to you?
34. How do you know when you’re connecting with someone?
35. What’s a lesson you’ve learned from a past relationship?
36. What’s your favorite memory with someone you love?
37. How do you handle feeling misunderstood?
38. What makes love last?
39. How do you feel about public displays of affection?
40. What kind of people feel easiest to be around?
MORE: 101 Spicy Questions To Ask Your Boyfriend Tonight
Life & Purpose
41. What’s your idea of a meaningful life?
42. What’s something you long for more of in your life?
43. What inspires you to keep going when things get hard?
44. What would your younger self be proud of today?
45. How do you stay grounded?
46. What’s something you’ve never tried but have always wanted to?
47. How do you define a fulfilling life?
48. What’s a personal milestone you hope to reach?
49. What’s your personal definition of happiness?
50. What’s something you’ve changed about your life for the better?
51. What do you hope to achieve in the next year?
52. What’s your dream for your future self?
53. What would you want people to remember about you?
54. How do you measure success in your life?
55. What motivates you to keep improving?
56. What’s something you’ve learned from a failure that set you up for success?
Values & Beliefs
57. What kind of legacy do you want to leave?
58. What does honesty mean to you in relationships?
59. What’s a belief you’ve outgrown?
60. What do you think is the most misunderstood aspect of your personality?
61. How do you approach forgiveness?
62. What are you most passionate about in your life right now?
63. What’s a truth you believe that others might think is crazy?
64. What do you think is the key to a good life?
65. What role does creativity play in your life?
66. What’s one value you think people should embody more?
67. What’s a common misconception about love that you disagree with?
68. How do you approach conflict resolution?
69. How do you evaluate the ethics of a situation?
70. How do you prioritize your personal and professional responsibilities?
71. How do you balance personal happiness with social responsibility?
Meaningful Connection
72. What’s a story from your life you love telling?
73. What makes a conversation feel meaningful to you?
74. What’s something you wish more people asked you about?
75. What brings you a sense of peace?
76. What’s something you would love to discuss more often with others?
77. What’s the best piece of advice you’ve ever received?
78. What’s a topic you could talk about for hours?
79. What do you most admire in other people?
80. What’s a skill or talent you wish more people knew you had?
81. What’s your favorite question to ask someone to get to know them?
82. What’s the most important thing you’ve learned about human connection?
83. What’s something people often misunderstand about you?
84. How do you express love in everyday actions?
85. What’s one thing you wish people would ask you more often?
86. How do you balance listening and sharing in conversations?
Fun & Playful
87. What’s your most embarrassing moment?
88. What’s the funniest way you’ve been injured?
89. What’s a myth or rumor you’ve heard about yourself?
90. What’s your most ridiculous fear?
91. If you could be any fictional character, who would you be?
92. What’s your favorite way to unwind after a tough week?
93. What’s the silliest thing you’ve ever done?
94. What’s the worst pickup line you’ve ever heard (or said)?
95. What’s something that always makes you laugh?
96. What’s a funny tradition in your family or culture?
97. If animals could talk, which would be the rudest?
98. If your life were a movie, what songs would be on the soundtrack?
99. What’s the weirdest thing you’ve ever seen?
100. What’s the most embarrassing thing you’ve worn?
101. What’s a guilty pleasure TV show or movie?
Great conversation doesn’t happen by accident.
It happens when we truly listen and allow ourselves to get to know someone.
If you want more connection, emotional depth, or just fewer awkward silences, keep these questions to get to know someone in your back pocket.
You never know where one great question might lead.
MORE: 115 Deep Questions To Ask Your Boyfriend
