50 Questions to Ask Your Best Friend
Some questions start a laugh, some start a two-hour conversation. Here are fifty of both — steal them for your next hangout, road trip or 1am call.
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You can know someone's coffee order, their ringtone and the exact face they make when they're annoyed — and still get surprised by their answer to a good question. That's the fun of it.
Use this list on a road trip, a slow afternoon, or one of those calls that was supposed to be five minutes. Skip around freely; there's no correct order.
Funny questions to warm up
- What's the most ridiculous thing you've ever cried about?
- If your life had a loading screen, what tip would it show?
- What's a food opinion you'd defend in court?
- Which of us would survive longer in a zombie movie, honestly?
- What's the weirdest compliment you've ever received?
- If you had to swap wardrobes with someone we both know, who's the least painful option?
- What's your most useless talent?
- What would the title of your autobiography be?
- Which cartoon character is basically you?
- What's the pettiest hill you're willing to die on?
Deep questions for real talk
- What's something you're proud of that you never bring up?
- When did you last change your mind about something big?
- What do you think people misunderstand about you?
- What's a fear you've mostly beaten?
- If you could redo one year of your life, which one and why?
- What does a perfect ordinary day look like for you?
- What's the best advice you've ever ignored?
- Who in your life do you wish you'd thanked properly?
- What are you quietly working toward right now?
- What's something you wish you'd learned earlier?
- When do you feel most like yourself?
- What's a compliment you've never forgotten?
- What would you do with a completely free year?
- What's the hardest thing you've ever had to say to someone?
- What do you hope stays exactly the same in five years?
Memory lane
- What's your very first memory of us hanging out?
- Which of our inside jokes has the strangest origin story?
- What's the hardest we've ever laughed together?
- What moment made you think 'okay, this is my person'?
- What's a small thing I did that you still remember?
- If we could relive one day we've spent together, which one?
- What's the best trouble we've ever gotten into?
- What did you think of me when we first met — be honest?
- Which photo of us is the most 'us'?
- What tradition of ours should we never drop?
Rapid fire — no thinking allowed
- Texting or calling?
- Beach trip or mountain trip?
- Big party or small dinner?
- Sweet or salty?
- Morning person or night owl?
- Plan everything or wing it?
- Rewatch a classic or try something new?
- Window seat or aisle seat?
- Cook together or order in?
- Board games or video games?
- Deep talk or dumb jokes (you can only keep one)?
- Would you rather know every secret I have, or have me know all of yours?
- Matching tattoos: yes, no, or 'only if tiny'?
- Who says sorry first, usually?
- Five more minutes or let's go now?
Frequently asked questions
How should we use these questions?
Take turns, don't rush, and follow the tangents — the detours are usually better than the list. Ten questions over good snacks beats fifty in a hurry.
Are these okay for new friendships?
Yes. Start with the funny and rapid-fire sections, and save the deep ones for when the friendship is ready for them.
What if we want to compare answers instead?
That's exactly what our two-player friendship test does — you both answer the same 15 questions separately, then see your match percentage side by side.