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 just times when you want to dig a little deeper into their psyches. (Like during a Zoom hangout, maybe?) But what do you ask? To inspire your conversation, here are a bunch of great options, from serious to silly.
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. If you had to get a tattoo right now, what tattoo would you choose?
22. If you could only eat one thing for the rest of your life, what would it be?
23. What is the best gift you’ve ever received?
24. Do you believe in aliens?
25. What do you think the most overrated holiday is?
26. Do you think you’ve ever encountered a ghost?
27. What is your favorite scent?
28. What is your favorite outfit?
29. Would you rather get a facial or a massage?
30. Would you rather go swimming in a pool or in the ocean?
31. What is your favorite type of vacation?
32. What is the most you’ve ever spent on something you absolutely did not need at all?
33. Have you ever accidentally sent a text complaining about someone to the exact person you were complaining about?
34. Would you ever considering naming a kid after yourself?
35. If you could either never have coffee again or never have dessert again, which would you choose?
36. What is the last time you laughed really hard?
37. When did you stop believing in Santa?
38. Did you ever pull out a tooth just to get money from the tooth fairy?
39. Is there a food you’ve surprisingly never had?
40. Would you rather take a shower or a bath?
Pop Culture Questions
41. What is the first book you remember really loving?
42. What is your most hated movie?
43. If you had to live in a home from one book, TV show, or movie, which home would you choose?
44. What TV show could you watch over and over again?
45. Which actor would play you in a movie?
46. Do you care about the Academy Awards, or do you think they’re dumb?
47. Who do you think is the best reality-show villain of all time?
48. If you had to be in a musical, which musical would you choose and who would you play?
49. Have you ever seen anything on Broadway? What would you want to see?
50. What was the first CD you ever bought?
51. What was the first band you ever saw live?
52. What is the first movie you remember seeing in a theater?
53. Do you like to listen to albums in full, or would you rather listen to a playlist?
54. Do you have a favorite painting?
55. 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?
56. What is your favorite franchise?
57. Who is your biggest fictional crush?
58. Who would you cast in The Secret History movie?
59. Do you think movies should be shorter in general, or no?
60. What is the most inspiring book you’ve ever read?
61. Who is your best friend?
62. What aspect of my personality do you think I need to change the most?
63. If you had to choose to never see me or your partner ever again, which one would you choose?
64. If you could change one thing about our friendship, what would you change?
65. Have you ever fallen in love with a friend but been too afraid to tell them?
66. Do you actually like Sally Rooney’s novels?
67. Do you feel like you maybe post to social media too much, or no?
68. What is the biggest lie you’ve ever told to me specifically?
69. Did you really read all of Proust or were you lying?
70. Should I get bangs?