80 questions to ask someone anonymously

You've opened someone's link and the box is empty. What now? Here are 80 questions that work well anonymously, grouped by mood, plus a few notes on asking questions people actually want to answer.

Light and fun

1. What's your go-to karaoke song?
2. What's the most useless talent you have?
3. Cats or dogs, and you have to defend it.
4. What's a food you'll never eat again?
5. What would your walk-up song be?
6. Which fictional character would you swap lives with for a week?
7. What's the last thing that made you laugh out loud?
8. What's your most-used emoji, honestly?
9. What would you do with a free day and no phone?
10. What's the worst haircut you've ever had?
11. Which app could you never delete?
12. What's your comfort film?
13. If you had a talk show, who's your first guest?
14. What's your toxic trait, but a funny one?
15. What's the most random thing in your bag right now?
16. Beach holiday or city break?
17. What's a song you secretly love?
18. What would you name a boat?
19. What's the best thing you've ever eaten at a party?
20. What's your hottest take about something completely unimportant?

Getting to know them

21. What does a perfect weekend look like for you?
22. What are you most looking forward to this year?
23. What's something you're weirdly good at?
24. Who taught you the most about life?
25. What's a skill you wish you'd learned as a kid?
26. What's your favourite memory from school?
27. What's the best advice anyone's ever given you?
28. Where would you live if money didn't matter?
29. What are you reading, watching or listening to right now?
30. What's the most spontaneous thing you've ever done?
31. What do people usually get wrong about you?
32. What's a small thing that makes your day better?
33. Which three words would your best friend use for you?
34. What's something you changed your mind about recently?
35. What would you do if you knew you couldn't fail?

Deeper ones

36. What's something you've never told anyone?
37. When did you last feel really proud of yourself?
38. What's a fear you've got over?
39. What's something you wish people asked you about more?
40. What do you need more of in your life right now?
41. Who do you miss?
42. What's the hardest thing you've had to forgive?
43. What would your younger self think of you now?
44. What's a moment that changed how you see things?
45. When do you feel most like yourself?
46. What are you still figuring out?
47. What's a promise you've made to yourself?
48. What do you hope people say about you when you're not around?
49. What's one thing you'd tell everyone if you knew they'd listen?
50. What's something you're quietly working on?

About them, from you

These work best when you know the person. They're compliments and observations framed as questions.

51. Do you know your laugh makes everyone else laugh?
52. How are you always so calm in a crisis?
53. Where do you get your style from?
54. Did you know you're the reason I started doing what I do?
55. How do you always know the right thing to say?
56. Has anyone told you you're a great listener?
57. What's your secret to being so organised?
58. Do you know how much that thing you did last month helped me?
59. Why are you so good at making new people feel welcome?
60. Have you ever thought about doing what you're good at for real?

Would you rather

61. Would you rather always be ten minutes late or always be an hour early?
62. Would you rather lose your phone or your wallet for a week?
63. Would you rather be famous for something embarrassing or unknown for something great?
64. Would you rather never hear music again or never watch a film again?
65. Would you rather know when you'll fall in love or who with?
66. Would you rather read minds or be invisible?
67. Would you rather have free food for life or free travel for life?
68. Would you rather relive one day or skip one day?
69. Would you rather be the funniest or the smartest person in the room?
70. Would you rather only text or only call for the rest of your life?

A little bold

Keep these for people who'd enjoy them, and keep them friendly.

71. Who in your life do you have a soft spot for?
72. What's your type, honestly?
73. Have you ever had a crush on a friend?
74. What's the boldest thing you've done for someone you liked?
75. What's the worst date you've ever been on?
76. Do you believe in love at first sight?
77. What's a green flag you look for in someone?
78. Have you ever been in love?
79. What's something someone did that made you like them instantly?
80. If I told you who I was, would you be surprised?

How to ask questions people want to answer

• Be specific. "What's your favourite film?" gets a title. "What film do you watch when you're sad?" gets a story.
• One question per message. A list of five gets one answer, or none.
• Ask about them, not about other people. Questions about someone's friends or exes put them in an awkward spot, and they usually go unanswered.
• Leave room for a no. People share more when a question doesn't corner them.
• Follow up. On DropAsecret a message is a conversation, so when they reply you can ask the next thing. See how replies work.

And keep it kind. Anonymity makes it easy to be blunt, and blunt is rarely what gets a real answer. Our guide to being a good sender has more.