60 questions to ask your best friend

These 60 questions to ask your best friend get you past “so, what’s new?” and into the kind of conversation you both remember. They start with easy catch-ups and get a little more personal as you go.

Best friends often know each other’s coffee order and worst ex, yet still run dry on a Tuesday night call. Every question here was written fresh for this page, so pick one, send it, and see what comes back.

What to ask instead of “how are you?”

These are just as easy to answer, and you’ll get a lot more back.

1. What’s been the best part of your week so far?
2. What are you watching, reading, or listening to right now that I should know about?
3. What’s something small that’s been annoying you lately?
4. What are you excited about this month?
5. Which part of your routine are you enjoying at the moment?
6. What’s the most interesting thing you’ve learned recently?
7. Who have you been spending the most time with lately?
8. What’s a bit of news you’ve been saving to tell me in person?
9. What would make this week a little easier for you?
10. What did you eat today that was actually good?
11. What’s your energy like these days, honestly, out of ten?
12. What’s on your calendar that you’re secretly excited about?

Fun questions to ask your best friend

Once you’re caught up, have a bit of fun. These are quick, a little ridiculous, and they work just as well in a group chat.

13. If we were a famous duo, who would we be?
14. What would be the title of the film about our friendship?
15. Which of us would get lost first on a road trip?
16. What’s a trend you secretly want to come back?
17. If you could only eat at one restaurant forever, which one?
18. What’s your most irrational fear?
19. If we opened a business together, what would it be, and who would be the boss?
20. What’s a song you’d put on a playlist called “us”?
21. What would your dream job be if money didn’t matter at all?
22. If you could swap lives with any celebrity for a week, who would it be?
23. What’s the strangest compliment you’ve ever received?
24. Which of our friends would survive the longest on a desert island?
25. What’s your go-to order at a bakery?
26. If you had to wear one outfit for the rest of your life, what is it?

Questions about your memories together

You’ll be surprised how differently two people remember the same day. Expect at least one “that’s not how it went”.

27. How would you describe the day we met to someone who wasn’t there?
28. When did you realise we were going to be close friends?
29. What’s a day with me you’d happily repeat?
30. What’s the story about us you tell at parties?
31. Which trip of ours had the best story, even if things went wrong?
32. What’s an inside joke of ours that still makes you laugh?
33. Was there a moment I showed up for you that you never forgot?
34. Which of your first impressions of me turned out to be completely wrong?
35. Which old picture of us makes you laugh every time?
36. What’s a tradition we have that you’d never want to lose?
37. What’s something I did years ago that you still tease me about?
38. Which season of our friendship has been your favourite so far?

Deeper questions for real talk

Save these for a quiet moment, when it’s just the two of you. Listen more than you talk, and let your friend pass on anything.

39. How are you, really, underneath the usual answer?
40. Is there anything you’ve been carrying on your own that you’d like to share?
41. What’s an achievement of yours that deserves more celebrating?
42. How can I be a better friend to you right now?
43. Who do you turn to first when something big happens, good or bad?
44. On a rough day, would you rather I call, text, or turn up with snacks?
45. What’s a lesson you learned the hard way?
46. Who in your life do you feel most yourself around?
47. Is there something you think I should hear, even if it’s awkward?
48. What’s one thing you’d like to change about how we keep in touch?
49. What part of getting older has surprised you most?
50. What do you admire most in the people you love?

Questions about dreams and the future

To finish, look ahead. Some of these answers might surprise you, even after years of friendship.

51. Where do you see yourself living in five years?
52. What’s one thing you want to do before next year ends?
53. What trip should we take together someday?
54. What do you want your life to feel like at fifty?
55. Is there a skill you’d love us to learn together?
56. What’s a dream you haven’t told many people about?
57. Picture us at eighty. What are we arguing about?
58. Which part of our friendship would you protect at all costs?
59. Where should we go to celebrate a big birthday someday?
60. What would you love us to still be doing together in ten years?

How to keep the conversation going

Answer your own questions too. A good conversation runs both ways, and so does a good friendship.

Go slow. Two or three good questions can easily fill a whole evening, so there’s no need to race through the list.

And if life gets busy, make it a habit. One question a day by message keeps you close through the hectic seasons. Need one right now? Send them today’s question of the day and pick the Friends option.

Our Little Thing works for friends too

When you set up Our Little Thing, you choose the kind of relationship first. Pick “Close friend” and the whole app is worded for friendship, with no romance. Friends get their own question packs: Everyday and Play are free, and Premium adds Real Talk, Deeper, Memories, Support and Dreams. The date ideas become things to do together.

You each answer the day’s question on your own, and both answers are revealed together once you’ve both replied. It works on one phone you pass back and forth, or you can pair two phones.

Want more? For a lighter game with friends, try our would you rather questions. For the people at home, there are 50 questions for family dinners, and if you’re after something for a partner, try these 100 questions to ask your partner.