Maybe it’s her birthday and you want something better than a card. Maybe you’re on a girls’ weekend and someone said, “Bet I know you better than you know me.” Or maybe a recent phone call made you realize there’s more going on in your best friend’s life than you knew — a new worry, a new person, a plan she hadn’t mentioned. Here’s a quiz, a big list of questions to ask your best friend, and a few thoughts on keeping a long friendship current.
In this guide
What does it actually mean to know your best friend?
There’s trivia knowledge — their middle name, their go-to coffee order, their celebrity crush in 2004. And there’s the kind that matters more: knowing what they’re carrying right now, how they want to be supported, and what they hope will happen next. Best friends who’ve been close for years usually ace the first kind and quietly slip on the second.
That slip is understandable. Adult friendships run on scraps of time: a voice note between meetings, a quick lunch, a group chat full of memes. And unlike a partner, a friend doesn’t share your kitchen: you only know what she chooses to tell you, in the scraps of time you get. The deep conversations that used to happen naturally at 2am now need a bit of intention. Without it, you end up loving a slightly older version of your friend, and they of you.
The best friendships aren’t the ones where you know everything. They’re the ones where you keep asking.
Questions to ask your best friend
Use these in person, over voice notes or on a long walk. For a game, each of you guesses the other’s answer first, then reveals.
- What’s your earliest memory of us?Friends often remember the beginning very differently, and it’s lovely to hear their version.
- Which song instantly puts you in a good mood?Easy, fun, and perfect for building a shared playlist.
- What’s the most embarrassing thing that happened to you that I don’t know about?Light, silly and great for laughing.
- If you could live anywhere for one year, where would you go?Reveals what they’re craving — adventure, quiet, family, sunshine.
- What’s a compliment you’ve never forgotten?Tells you what they most want to be seen for — and gives you a chance to say it again.
- What’s been hardest about this year so far?A gentle invitation to the real stuff.
- What do you need from your friends when things go wrong?Advice, venting, distraction, food — it’s worth knowing rather than guessing.
- Which of your family members are you most like?Often opens up stories about where they come from.
- What’s a dream you’ve almost given up on?Tender. Listen without immediately trying to solve it.
- What’s a small thing that makes your week better?Useful knowledge for the next time they’re having a rough one.
- What’s one way you’ve changed in the last five years?Helps you meet the current version of your friend.
- What’s something you wish people asked you about more?Often their quiet passion or a part of life no one notices.
- When did you feel closest to me?A sweet one. Prepare for it to be a moment you’d forgotten.
- Is there anything I do that annoys you, that you’ve never mentioned?Brave, but good friendships can handle it — and it keeps resentments from growing.
- What are you looking forward to most right now?Ends on a hopeful note and gives you something to ask about next time.
How to turn this into a best friend quiz game
Take the quiz above, then send it to your best friend and compare. Or skip the screen entirely: each of you writes down your guess for the other’s answer to five questions from the list, then swap. Points are optional. Laughing is not.
Long-distance best friends can do this over voice notes — one question a day for a week is a surprisingly sweet ritual. Groups of close friends can play it at a birthday dinner, with each person answering about the person on their left.
Whichever way you play, keep it kind. If someone gets an answer wrong, the right response is “ooh, tell me,” not “how do you not know that?” The point is closeness, not a test.
When you realize you’ve drifted a little
Sometimes a quiz like this lands with an uncomfortable thought: I don’t really know what’s going on with them anymore. That’s worth noticing, not worth panicking about. Most long friendships go through quieter seasons — new babies, new cities, divorces, demanding jobs, caring for aging parents. Drifting a little is part of how friendships survive those years, not a sign they’re failing.
What brings people back is usually small and direct. Send the text you’ve been meaning to send. Suggest a specific plan instead of a vague “we should catch up.” Ask one real question and actually wait for the answer. If you’re unsure how to say it, practice the words out loud with someone else first; often it’s as simple as “I miss you, and I feel like I’ve lost track of your life — can we fix that?”
And if the friendship has changed shape for good, that can be okay too. Some best friends become the people you see twice a year and pick right back up with. Knowing them well can mean knowing that.
Sometimes it helps to say the messy, unfiltered version out loud to someone who won’t judge it. That’s Iris — text her like you’d text a close friend, and she’ll help you untangle it. She remembers the thread, so next time you can pick up right where you left off.
Frequently asked questions
What questions should I ask my best friend?
Mix fun questions with real ones. Try “What’s your earliest memory of us?”, “If you could live anywhere for a year, where would you go?”, “What’s been hardest about this year?” and “What are you looking forward to most?” Guessing their answer first makes it a game.
How do you know if someone is really your best friend?
They’re the person you want to tell first, good news or bad, and they make time for you when it matters. You can be honest with each other, disagree without fear and pick back up after time apart. Knowing every detail isn’t required; trust and mutual effort are.
How well should you know your best friend?
Well enough to know what’s going on in their life now, how they like to be supported and what matters most to them. You don’t need to know every fact. Staying curious about who they’re becoming is more important than remembering everything about who they were.
How do you play a best friend quiz?
Each of you answers questions about the other — favorite song, biggest fear, dream trip — then compare. Take turns, keep it playful and follow up on surprising answers. You can also take an online quiz separately and compare results over text.
What should I do if I feel like I don’t know my best friend anymore?
Reach out directly with a specific invitation and a real question about their life. Most friendships drift during busy seasons, not because anyone stopped caring. Saying “I miss you and want to catch up properly” is usually welcomed — and often it’s exactly what they were hoping to hear.