Deep Questions to Ask Friends
For friends who want to talk about more than plans: late at night, on a long drive, at a sleepover, or when you're bored and done with small talk. The 96 questions are sorted into six groups: Easing in, Growing up, Hopes and fears, Big questions, For the group (the friendship itself, asked around a whole circle) and For best friends (for two people who already know each other well). Each group runs from easy to harder, and each question has a note on how to ask it, what to listen for or what to do when an answer turns out to be heavy.
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The questions
Each question, and why to ask it
Easing in
When did you last feel completely like yourself?
Why ask it
A good first question because nobody can get it wrong. Listen for whether the answer is a place, an activity or a particular person, then ask what gets in the way of feeling like that the rest of the time.
What do people get wrong about you when they first meet you?
Why ask it
Quiet friends get called stuck-up and loud ones get called confident, and both are tired of it. After each answer, the others can say when they stopped believing it, which turns a complaint into a compliment.
Where does your mind go in the last few minutes before you fall asleep?
Why ask it
It sounds light, and some people will say tomorrow's lunch. Others replay conversations or plan a whole imaginary life, and either answer is fine. If someone says the nights are when they worry, ask what helps and leave it there for now.
What could you talk about for an hour that nobody ever asks you about?
Why ask it
Whatever they name, ask about it on the spot. You will usually get a five-minute answer about a hobby, a sibling or a plan they assumed nobody cared to hear, and that is the question working.
What small thing can turn a bad day around for you?
Why ask it
Worth remembering as well as hearing: a certain snack, a walk, ten minutes with a pet. The next time that friend is having a rough day, you already know what to bring.
Is the texting version of you braver, funnier or quieter than the one in the room?
Why ask it
Most people have a clear answer and a reason, which makes it an easy early question. A friend who is braver in messages may be telling you where a hard conversation with them should start.
Which three words would you use to describe yourself, and which one would your family argue with?
Why ask it
The three words are the warm-up and the argument is the question. It shows the gap between how someone sees themselves and how they are seen at home, with a joke attached so nobody has to get serious yet.
What are you quietly good at that almost nobody has seen you do?
Why ask it
Bragging feels risky, so the question hands out permission. If someone stalls, let a friend answer for them, because being told what you are good at by someone who has watched you is the better version anyway.
What song says something about you that you would struggle to say yourself?
Why ask it
Let people play thirty seconds of it if a speaker is handy. Don't make them explain the lyrics line by line, since picking the song was the brave part and the explaining can wait.
What did someone do for you this year, without being asked, that you still think about?
Why ask it
Gratitude is an easy way into feelings because nobody is exposed by it. Pay attention to what kind of help it was, since people remember the thing they needed most at the time.
What is your happiest memory that has no photo to prove it?
Why ask it
With no picture to lean on, people have to describe it: the light, who was there, what was on the table. It is often a small scene and not a big event. Ask whether anyone else who was there remembers it the same way.
What do you do differently when nobody is watching?
Why ask it
Keep this one at the level of singing to the dog or dancing while brushing teeth, and let the laughs do their job. Friends who have confessed to a private dance routine find it easier to answer whatever comes after.
What story, from a book, a show or a game, changed how you see something real?
Why ask it
Push past the title to the change itself. 'It made me think about my grandpa differently' is the answer you are after, and it often comes only after someone asks 'changed it how?'
What advice do you give other people and never follow yourself?
Why ask it
Admitting it gets a laugh, whether the advice is 'go to bed earlier' or 'just text them back'. Friends are then allowed to quote it back the next time it applies.
What did you care a lot about two years ago that barely matters to you now?
Why ask it
Answers run from a brand of shoes to one particular person's opinion. Hearing a few in a row is a gentle reminder that whatever feels huge this month may end up in the same pile.
Growing up
What is your earliest memory, and how sure are you that it really happened?
Why ask it
'How sure are you' lets people admit the memory might come from a photo or a story told at dinner. Ask what they can see in it: a floor, a color, someone's shoes.
What did you want to be when you were little, and what did you like about the idea?
Why ask it
The job is less interesting than the reason. A kid who wanted to be a vet for the animals and one who wanted it for the white coat grew into different people, and both can usually still find that kid in themselves.
Who did you look up to when you were little, and do you still?
Why ask it
An older cousin, a babysitter and a cartoon character are all fair answers. 'Do you still' is where it gets interesting: some heroes hold up, and some turn out to have been the nearest person who could drive.
What part of being a kid do you miss the most?
Why ask it
What gets missed is more often a kind of time than a toy: long summers, nobody expecting a decision from you, a blanket fort that counted as a real building. Friends who are still close to being kids can answer too, and their answers are no smaller.
Who was your first real friend, and what happened to that friendship?
Why ask it
Many first friendships end with a move or a new school and no goodbye at all. Don't be surprised if someone gets a little sad about a kid they last saw at seven. That's a fair thing to be sad about.
What rule in your house made no sense to you until you were older?
Why ask it
For anyone still living under the rule, 'it still makes no sense' is a fully acceptable answer, and the others can vote. No phones at dinner and calling the moment you arrive are fair game.
What did the people who raised you get right that you only noticed later?
Why ask it
Worded this way so it fits every kind of family: parents, grandparents, a stepparent, an older sibling. It's an easier door into family talk than asking what went wrong, and someone who has little to say should be allowed to say little.
What do you understand about one of your parents now that you didn't when you were small?
Why ask it
Usually it's that they were tired, worried about money or younger than they seemed. Not everyone has a parent they can speak about easily, so offer 'or any adult who raised you' and let anyone pass.
Who outside your family helped raise you, even a little?
Why ask it
A neighbor, a coach, a friend's mom who always set an extra place. Ask whether that person knows. Quite often they don't, and a message to them is a good thing to come out of a late-night conversation.
What would your ten-year-old self be most surprised by in your life now?
Why ask it
Most people start with a joke about staying up late or owning a phone, then get to something real. Give the second answer room. If it comes out harsh, ask what the ten-year-old would be impressed by, because there is always something.
What were you like in middle school, and would you have been friends with that kid?
Why ask it
Anyone who is in middle school right now can swap in elementary school. Being kind about an awkward earlier self takes some effort, so give the 'would you have been friends' part time. Friends who were there may defend the kid better than the speaker does.
What did you worry about as a kid that the adults around you never knew?
Why ask it
Small worries and big ones both belong here, from a wrong answer in class to a parent not coming home from work. If a friend shares a big one, thank them and don't measure it against anyone else's.
What were you told about yourself as a kid that you ended up believing?
Why ask it
Labels like 'the shy one' or 'the difficult one' can stay on long after they stop fitting, and friends are well placed to say so. Ask whether they still see it, and let them be honest in the kind direction.
What moment made you feel grown up for the first time?
Why ask it
Sometimes it is a proud one, like a first paycheck or a solo trip. Sometimes it is the day they had to look after someone else. Let the person decide which kind of story it is before you react.
What did nobody explain to you that you had to work out by yourself?
Why ask it
If someone in the circle is younger or newer to it, the answers double as the explanation they never got. How to make friends at a new school and how money works are the kind of thing people name.
What would you tell yourself at thirteen, and would you have listened?
Why ask it
The advice is usually the same few things: relax, be kinder, stop worrying what that one crowd thinks. The honest part is 'would you have listened', where plenty of people admit they wouldn't have heard a word of it. A friend who is thirteen now can pick nine.
Hopes and fears
What about the future excites you more than it scares you?
Why ask it
A hopeful one to ask before any talk of fears. Moving out, a trip, simply being older: whatever they pick, ask what they picture first when they think about it.
In the life you're hoping for, what does a normal weekday morning look like?
Why ask it
An ordinary morning is easier to describe than a whole life plan, and more revealing. Notice who else is in the picture, where it is and whether work comes up at all.
What are you proud of that has nothing to do with grades, work or winning?
Why ask it
Taking away the usual scoreboards makes people stop and think. Good answers are things like being the one a little cousin runs to, or having stayed friends with someone through a hard year. Don't let anyone shrug theirs off.
What kind of person are you trying to become, and who gave you the idea?
Why ask it
Often there's a real person behind it: an aunt, a teacher, an older kid who was kind when they didn't have to be. The distance between who a friend is and who they are aiming at is something to cheer for, never to tease.
What dream have you carried for so long that saying it out loud makes you nervous?
Why ask it
Agree before anyone answers that nobody says 'be realistic'. A dream told to friends for the first time needs a 'tell me more', and practical questions can wait for another day.
What would you try this year if you could be sure that failing would stay private?
Why ask it
For plenty of people the fear is being seen to fail, more than the failing itself. Once you know what the thing is, a friend can offer to be the only witness: the one person at the audition, or the first reader.
What fear have you beaten, and how did you do it?
Why ask it
The method matters more than the fear: some people went straight at it, some were dragged along by a friend, and some just got older. Anyone in the circle still stuck on theirs gets a few ideas for free.
What do you feel pressure to be, and where is the pressure coming from?
Why ask it
'Where is it coming from' is the useful part, because pressure with a source can be talked about, whether that is a parent, a team or a feed. Just listen: it isn't the moment to defend the parent or the coach.
What is your biggest fear that isn't an animal, a place or a scary film?
Why ask it
Ruling out the easy answers points people at the real ones: being left behind, letting someone down, ending up stuck. Go first if you ask it, and make your answer the size you would want back.
What time of the day or week is hardest for you, and why that one?
Why ask it
A way of asking about loneliness or dread without using either word. Sunday evening and the hour after everyone logs off are typical answers, and a friend who knows your hard hour can text you during it.
What have you given up on that you'd pick back up if someone believed in you?
Why ask it
If you do believe in them, say so plainly and then follow up next week, whether it was drawing or an instrument that went back in the closet. Asking is only kind if someone remembers the answer.
What are you tired of pretending to be fine with?
Why ask it
It might be small, like a nickname or always being the driver. It might be big. If it is about someone in the room, hear it out before explaining yourself, because the person has likely rehearsed saying it for a while.
When did you last cry, and did anyone know?
Why ask it
Some people will answer 'yesterday, at a dog video' and some will go quiet, and neither needs a comment. If the answer to 'did anyone know' is 'no one', a simple 'you could have told me' is worth saying once.
What insecurity of yours do you think would surprise us?
Why ask it
Better with two or three friends than a full room, and nobody has to answer. If you are surprised, say so, since that is the kind response. Don't argue them out of it with a list of reasons: 'I never would have guessed, and I don't see it' is enough.
What is your biggest regret so far, and what did it teach you?
Why ask it
The words 'so far' keep it in proportion, which matters for younger friends who feel one mistake has defined them. Don't rush to say it wasn't their fault. Ask what they would do now, and let them be the one who learned something.
What hard thing have you gotten through that you're a little proud of?
Why ask it
It asks about the getting through, so nobody has to describe the worst of it. A failed class, a move or a rough year at home all count, and one sentence is a complete answer. If what a friend shares sounds like more than friends can carry, it is okay to say so and help them think of an adult they trust.
Big questions
What does being happy mean to you: a feeling, a kind of day or something else?
Why ask it
The three options are there to get people started, and most end up inventing a fourth. Compare answers around the circle. Friends who have known each other for years are often surprised to find they are chasing different things.
Who is the best person you know, and what makes you say so?
Why ask it
Easier than defining goodness in the abstract. The reasons given, like patience, showing up or never talking behind backs, are a list of what the speaker values most. Someone may name a person in the room, and that should be allowed to land.
Would you rather be liked, respected or understood, if you could only have one?
Why ask it
Have everyone answer on the count of three so nobody copies. The split tells you a lot: the friend who picks 'understood' may be saying they don't feel it yet.
How can you tell when someone really loves you?
Why ask it
Family and friends count as much as romance, so say that before people answer. Listen for whether it is words, time or small acts, like someone remembering how you take your toast. That detail tells friends how to show up for each other.
Do you think some people are meant to meet, or is it all chance?
Why ask it
Friends tend to use each other as the evidence, which is half the pleasure of it. There is no need to settle it. Ask the people on the chance side whether that makes a good friendship feel less special or more.
When have you felt very small in a good way?
Why ask it
A night sky, the ocean, a stadium singing one song. It gives a serious conversation somewhere to breathe, and the answers are short. Ask whether they ever went looking for the feeling again.
What would make you feel successful even if nobody else ever found out?
Why ask it
Taking the audience away is the point. Some friends find their answer barely changes, and some notice that half of what they are working toward is for show. Give either discovery a minute of quiet before the next person goes.
Do you think everyone else feels as unsure on the inside as you sometimes do?
Why ask it
Go around the whole circle with it. Hearing the friend who seems most confident say 'yes, constantly' is often the most reassuring moment of the night, especially for anyone still at school.
What is worth being uncomfortable for?
Why ask it
Ask for the last time they chose the uncomfortable thing, whether that was an apology, a hard practice or standing up for someone. An example keeps the answer from turning into a slogan.
What do you believe that the people who raised you don't?
Why ask it
It can be as small as how to spend a weekend or as large as faith or politics, and each person chooses the size. Treat every answer as a report, not the start of a debate, and don't press on whether the family knows.
Have you ever forgiven someone who never said sorry?
Why ask it
Names aren't needed, and 'not yet' is an honest answer. Ask what changed for them afterward, if anything did. Nobody should be talked into forgiving a person tonight.
If you could know one thing for certain about your future, would you want to, and what would you ask?
Why ask it
Some friends refuse outright, and their reasons are worth hearing. For the ones who would ask, the thing they want to know points straight at what they are most anxious about, so follow up gently.
When things get hard, do you pray, wish, talk to someone who isn't there, or none of those?
Why ask it
A sideways way into what a person leans on. Religious friends and non-religious friends can both answer without a debate starting, as long as the reply to every answer is curiosity.
What do you hope happens after we die, and what do you think really does?
Why ask it
Splitting hope from belief lets a friend answer without defending a position. People bring faith, doubt and sometimes a recent loss to it, so it only works if nobody tries to win. Leave it for another night when someone present is newly grieving, unless they are the one who raises it.
What do you think you are here to do, if anything?
Why ask it
The words 'if anything' are a way out for people who find the idea of a purpose heavy. 'Be decent and enjoy it' is a full answer. Don't let the one friend with a five-year plan make everyone else feel behind.
At ninety, what would make you say it had been a good life?
Why ask it
Pay attention to what gets left out as much as what gets said: if nobody brings up money or grades, it's fine to point that out afterward. A kind way to close a serious night, because people go home thinking about what they want more of.
For the group
What is each of us better at than we give ourselves credit for?
Why ask it
Take one person at a time and have everyone else answer about them. The person being described is only allowed to say thanks. It takes a while, and it is the part of the night people remember.
What have you learned from someone in this room?
Why ask it
It could be a skill, like parallel parking, or a way of being, like how to apologize quickly. Say the name, because the friend named often had no idea they taught anything.
What moment with this group would you put in a time capsule?
Why ask it
Expect ordinary ones to win: a parking lot, a kitchen floor, a bus ride back from somewhere. If two people pick the same moment, have them each tell it and compare the versions.
What did you think friendship would be like when you were younger, and how is the real thing different?
Why ask it
TV promised one inseparable gang and a tree house. Real friends turn out to be busier and more complicated, and many people decide that's better. A gentle way to start talking about the friendships in the room.
What does a friend have to do before you fully trust them?
Why ask it
Ask for the moment it happened with someone, since trust usually has a date: a secret that stayed kept, a friend who showed up when it was inconvenient. People in the room may hear the exact thing they once did.
What do you do in front of us that you would never do in front of anyone else?
Why ask it
Underneath the joke about a weird laugh or crying at cartoons, each answer is a way of saying 'I feel safe with you'. It is worth hearing it that way.
When has being with us made you braver than you would have been alone?
Why ask it
Ask who in particular gave the push, whether it was toward an audition or toward talking to someone new. The reckless kind of brave doesn't count, and the others can say so with a laugh.
When has one of us stood up for you?
Why ask it
Sometimes the friend who did it has forgotten, and sometimes they never knew it mattered. If someone can't think of a time, don't treat that as an accusation. Move along, and let everyone quietly take note.
What kind of friend are you on a good day, and what kind on a bad one?
Why ask it
Make everyone give both parts. If someone can only describe the bad day, the others supply the good one for them. The bad-day answers, like going silent or canceling late, tell friends what not to take personally.
Who here has changed the most since we met, and how?
Why ask it
Frame it as growth before anyone answers, so nobody hears 'you used to be worse'. The person named gets the final word on whether the others have it right.
What do you predict each of us will be doing ten years from now?
Why ask it
Fun for a while, then quietly revealing, because a prediction shows what friends see in someone. Keep them generous. If one stings ('still in this town'), the person it's about can swap it for their own.
What would you like us to talk about more than we do?
Why ask it
Often the answer is 'real stuff, like tonight'. Sometimes it's a particular subject, such as money, family or what happens after graduation. Pick one thing from the answers and talk about it before the night ends.
What joke of ours would you like us to retire?
Why ask it
Most circles have a running bit that stopped being funny to its target a while ago. Whoever speaks up has probably put up with it for months, so the only acceptable response is 'done', with no defense and no 'but it's funny'.
What worries you most about friendships: growing apart, being replaced or being too much?
Why ask it
Giving three common fears means nobody has to invent theirs from scratch. People often say 'all three', and a circle where everyone has admitted that is a little easier to be in afterward.
When have you felt left out by us, even if nobody meant it?
Why ask it
Only for friends on good terms, and never on a night when someone is already upset. 'Even if nobody meant it' lets people say it without accusing anyone. Listen, apologize if it's yours to apologize for, and skip the explanation of why it happened.
How should we handle it when two of us fall out?
Why ask it
Much easier to talk about while everyone is getting along. Useful ground rules tend to come out of it: nobody has to pick a side, nothing gets argued in the group chat, and somebody checks on both people.
If our friendship had one rule written on the wall, what should it be?
Why ask it
'What's said here stays here' usually gets proposed first, and it deserves a vote. Funny rules are welcome too. The winner tends to get quoted for a long time.
For best friends
Would we still have become friends if we had met for the first time this year?
Why ask it
A warm place to start with one close friend. Most pairs decide yes, though for different reasons than the first time around, and the reasons are a picture of what each of you values in the other now.
How would you describe our friendship to someone who has never had a best friend?
Why ask it
Having to explain it to an outsider forces real words where there is usually just a shrug. Trade answers. The two descriptions rarely match, and neither one is wrong.
What was the first real secret you told me, and were you nervous?
Why ask it
You may each remember a different moment as the one where it got real. Hearing that your reaction back then is the reason they kept telling you things is a quiet reward for having listened well.
What did you notice about me early on that turned out to be true?
Why ask it
Kinder than asking for a first impression that was wrong, because it says 'I saw you correctly from the start'. Ask what gave it away. It is usually something small you did without thinking.
How have I changed you, for better or for worse?
Why ask it
Usually it is a mix: braver, later to everything, into a band they once mocked. Take the 'for worse' half with good humor, since it's often said with love and is sometimes accurate.
What would be different about your life if we had never met?
Why ask it
Go past 'I'd be bored' to the specifics: a class they would have dropped, a town they would not know, a person they met through you. Then answer it yourself, because the question is lopsided if only one of you gets told.
What is easy to tell me and hard to tell everyone else?
Why ask it
The answer marks out what this friendship is for. It might be family things, crushes, or doubts about a plan everyone else is excited about. Whatever it is, treat it as a job you have been trusted with.
When have you needed me and not asked?
Why ask it
Hard to hear without getting defensive. Skip 'you should have told me' and ask what would have made it easier to reach out, then offer the same information about yourself.
What should I do when you say you're fine and I can tell you're not?
Why ask it
Push once, wait, bring food, send a meme and say nothing: every friend wants something different. Get an actual instruction and follow it next time, because that's how the question pays off.
What would you want me to say to you on your worst day?
Why ask it
Some people want 'this isn't your fault' and some want 'get up, we're going for a walk'. Write it down if you have to. It is a rare chance to be handed the exact words in advance.
What do you want me never to do, even as a joke?
Why ask it
Don't ask for the reason, even when the answer is as small as not reading messages over their shoulder. Agree, and then keep to it, because the keeping is what builds trust.
What is the hardest part of being my friend?
Why ask it
Only ask if you want the answer, and decide beforehand that you will say thank you and nothing else for at least a minute. It's usually something you already half knew, like going quiet when stressed or being hard to make plans with.
What is the biggest difference between us, and has it ever worried you?
Why ask it
Naming the difference tends to shrink it, whether that is two very different families or one of you leaving and one staying. If a worry does come out, talk about what you would both do, and don't promise that nothing will change.
Is there anything you have wanted to apologize to me for?
Why ask it
Often it's something the other person forgot long ago, which makes forgiving it easy. If it's something that did hurt, say so honestly and then accept the apology. Offer one of your own if you have it, but don't invent one to even things out.
If we ever stopped being close, what would you miss first?
Why ask it
It sounds sad and rarely is. The answers are small and exact, like a running commentary during movies or having someone to send a photo of a weird dog to. Those are the things worth protecting when life gets busy.
What do you hope never changes about us, and what do you hope does?
Why ask it
Hoping something changes takes more courage to say than hoping it stays: more honesty, more time in person, less being the one who always texts first. Take a requested change as a sign the friendship matters enough to work on.
How to ask deep questions with friends
Practical guidance for the conversation itself
Before you go deep
Pick a setting where nobody has to hold eye contact
Deep talk often comes easier side by side than face to face: sleeping bags in the dark, the back seat on a long drive, a walk home, a call with the cameras off. If everyone is sitting in a bright room looking at each other, do something with your hands while you talk, like cards or snacks.
Agree on three things first
Anyone can pass on any question without giving a reason. What gets said stays with the people who heard it, which means no screenshots, no recording and no retelling at school on Monday. And nobody laughs at an answer unless the person answering laughs first. Saying these out loud takes twenty seconds and changes what people are willing to say.
Start with Easing in, even with old friends
Two or three easy questions show everyone how the night is going to go: people listen, nobody gets mocked, a short answer is fine. Jumping straight to regrets and insecurities, with no run-up, tends to get silence or jokes.
Whoever asks also answers
A friend who only asks is running an interview. Answer every question you ask, and on the heavy ones go first, with something real and about the size you would like to hear back. The others will match you.
Ways to use the list
The sleepover or late-night round
Lights low, one phone with the list on it. The person holding the phone picks a question, everyone answers, and the phone moves on. Four or five questions is a full night: one from Easing in, one or two from Growing up or Hopes and fears, one from For the group, and something lighter before sleep.
The long drive
The passenger reads and the driver chooses the group of questions. Big questions suit a car well, because there is time to disagree kindly and nowhere anyone needs to be. Keep anything that might bring tears for when the driver is parked.
When you're bored on a call or in the group chat
Send one question and answer it yourself in the same message, so nobody has to go first. Easing in and Big questions work in text. Keep For the group and the later Hopes and fears questions for when you can hear each other, because tone goes missing in a chat and a heavy answer can sit there unanswered.
Two best friends, trading
Take turns choosing from For best friends, and both answer every question before moving to the next. Three in one evening is plenty. The later ones ask what is hard about the friendship, so pick a night when you are both rested and getting along.
When an answer is heavy
What to say straight after
Thank them, and then wait. 'Thanks for telling us' followed by a few seconds of quiet does more than advice. Don't fix it, don't say it could be worse, and don't answer with a bigger story of your own. Then ask one thing: 'Do you want to say more, or should we move on?'
If someone cries or goes quiet
Tears don't mean the night has gone wrong. Pass the tissues, stay where you are and don't make a scene of it. If a friend goes quiet, let them, and check in privately later with a message that asks for nothing back.
When it is more than friends can carry
Keeping things private has one exception, and it helps to say so at the start. If a friend tells you they are being hurt, or that they are thinking about hurting themselves, being a good friend means helping them reach an adult they trust, such as a parent, a school counselor or a doctor, and offering to go with them. Getting someone help is not the same as breaking their trust.
Come back up before you stop
Finish somewhere lighter than the heaviest answer of the night. Ask the time capsule question, or the happiest memory with no photo, or just put on a film. People should leave feeling closer, and a night that ended in laughing is easier to say yes to again.