50 Questions to Ask Your Best Friend (That You've Never Asked)

You've been friends for years. You know their embarrassing stories, their relationship history, their family drama. You can communicate in looks and half-sentences.

But here's the thing: people change. Your best friend isn't the same person they were five years ago, and neither are you. These questions help you discover who they're becoming.

Questions You've Probably Never Asked

1. What's something you've changed your mind about recently?
2. What do you wish more people asked you about?
3. What's the hardest thing about being you right now?
4. What's something you're better at than you give yourself credit for?
5. What do you want but feel guilty wanting?

Questions About Your Friendship

6. What did you think of me when we first met?
7. When did you realize we were going to be real friends?
8. What have I taught you without knowing it?
9. What do you wish we talked about more?
10. What's something you've never thanked me for?

Would You Rather (Best Friend Edition)

11. Would you rather know everything I'm thinking or have me know everything you're thinking?
12. Would you rather always have to tell the truth or always have to lie?
13. Would you rather we live in the same city forever or both live abroad?
14. Would you rather I tell you hard truths or comfortable lies?
15. Would you rather we start a business together or travel the world together?

Deep Questions for Late Nights

16. What are you afraid to want?
17. What would you do differently if no one would judge you?
18. What's the loneliest you've ever felt?
19. What do you need to hear right now?
20. What part of yourself are you still trying to understand?

How to Use These Questions

Don't barrage your friend with 20 questions in one sitting. Pick 2-3 that feel right for the moment. The goal is conversation, not interrogation.

And remember: these questions work both ways. Be ready to answer what you ask.

Want an endless supply of friendship questions? Spark organizes hundreds of questions by mood and depth level.

[Try Spark Free →]