No matter how comfortable you feel with your close friends, there are going to be times in your relationship when you have to fill awkward silences or times when you want to dig a little deeper into their psyches. “Just like any relationship, the way to get to know people is to ask them about themselves. When you ask these questions, you get to learn different parts of them that you might not know just by going through everyday life together,” says Meaghan O’Neil, a Seattle-based licensed marriage and family therapist associate. She adds that one question “can then spark a new topic for you all to keep deep diving, which just allows you to keep going into new parts of them that maybe you wouldn’t have discovered otherwise.”
There are plenty of times to spark these sorts of conversations (like on a vacation together, maybe, or when you’re out to dinner). But what do you ask? To inspire your conversation, here are a bunch of great options from serious to silly.
Personal Questions
1. Are you happy about where you are in your career?
2. Which of your family members are you closest to?
3. How did you picture your life at this age when you were young?
4. What is the first thing you do when you wake up in the morning?
5. Do you try to spend time at night without your phone?
6. When is the last time you wrote a letter to someone?
7. What was your favorite hobby as a kid?
8. What is your love language?
9. Do you believe in astrology? Why or why not?
10. Do you feel like the internet has had more of a positive or negative effect on society?
11. If you could change one thing about your personality, what would it be?
12. Do you ever procrastinate?
13. Where do you want to travel to the most?
14. Who was your first crush?
15. What was your most embarrassing moment?
16. What is your biggest pet peeve?
17. What is your favorite place to be in the world?
18. What is the craziest lie you’ve ever told?
19. How do you deal with stress?
20. What habit are you trying to quit — or form?
21. What traits, if any, do you think you got from your parents?
22. What is your attachment style?
23. Do you have a morning routine? If so, walk me through it.
24. Do you believe in soulmates?
25. What activity makes you feel the most fulfilled?
26. What’s your biggest fear in life?
27. What’s something you wish you were better at?
28. When was your first heartbreak?
Fun Questions
29. If you had to get a tattoo right now, what tattoo would you choose?
30. If you could eat only one thing for the rest of your life, what would it be?
31. What is the best gift you’ve ever received?
32. Do you believe in aliens?
33. What do you think the most overrated holiday is?
34. Do you think you’ve ever encountered a ghost?
35. What is your favorite scent?
36. What is your favorite outfit?
37. Would you rather get a facial or a massage?
38. Would you rather go swimming in a pool or in the ocean?
39. What is your favorite type of vacation?
40. What is the most you’ve ever spent on something you absolutely did not need at all?
41. Have you ever accidentally sent a text complaining about someone to the exact person you were complaining about?
42. Would you ever considering naming a kid after yourself?
43. If you could either never have coffee again or never have dessert again, which would you choose?
44. What is the last time you laughed really hard?
45. When did you stop believing in Santa?
46. Did you ever pull out a tooth just to get money from the tooth fairy?
47. Is there a food you’ve surprisingly never had?
48. Would you rather take a shower or a bath?
49. How would you describe your personal style?
50. What song would you put on a “do not play” list at your wedding?
51. What’s the best Halloween costume you ever wore?
52. If you could only wear one brand for the rest of your life, which would you choose?
53. What’s the best gift someone ever gave you?
54. What’s your favorite Halloween candy?
55. Have you ever seen a psychic?
Pop-Culture Questions
56. What is the first book you remember really loving?
57. What is your most hated movie?
58. If you had to live in a home from one book, TV show, or movie, which home would you choose?
59. Which TV show could you watch over and over again?
60. Which actor would play you in a movie?
61. Do you care about the Academy Awards, or do you think they’re dumb?
62. Who do you think is the best reality-show villain of all time?
63. If you had to be in a musical, which musical would you choose and who would you play?
64. Have you ever seen anything on Broadway? What would you want to see?
65. What was the first CD you ever bought?
66. What was the first band you ever saw live?
67. What is the first movie you remember seeing in a theater?
68. Do you like to listen to albums in full, or would you rather listen to a playlist?
69. Do you have a favorite painting?
70. Would you say you know a lot about art, or would you say you know pretty much almost nothing about it and actually you’re not even particularly interested in it at all?
71. What is your favorite TV franchise?
72. Who is your biggest fictional crush?
73. What would you want to find inside the Criterion Closet?
74. Do you think movies should be shorter in general, or no?
75. What is the most inspiring book you’ve ever read?
76. If you had to go on one existing reality-TV show, which would you choose?
77. Which fictional character would you pick to be your best friend?
78. What’s your favorite red-carpet look of all time?
79. If you could see any stand-up comedian live, who would you pick?
80. Which former Real Housewives of New York star do you wish was still on TV?
81. What do you think are the three best rom-coms of all time?
82. Who’s your favorite nepo baby?
83. Which outlandish celebrity rumor is your Roman Empire?
Dangerous Questions
84. Who is your best friend?
85. What aspect of my personality do you think I need to change the most?
86. If you had to choose to never see me or your partner ever again, which one would you choose?
87. If you could change one thing about our friendship, what would you change?
88. Have you ever fallen in love with a friend but been too afraid to tell them?
89. Do you actually like Sally Rooney’s novels?
90. Do you feel like you maybe post to social media too much, or no?
91. What is the biggest lie you’ve ever told to me specifically?
92. Did you really read all of Proust or were you lying?
93. When was the last time you were annoyed with me?
94. Who was your least favorite of my exes?
95. Have you ever kept a secret from me?
96. Who are you jealous of?
97. Would you ever work for me?
98. Who are you voting for?
99. Who do you have muted on social media?
100. Should I get bangs?