Questions to Ask Your Friends
For groups of friends who already know each other's coffee orders and want something better than small talk. The 171 questions are sorted into six groups: Funny, Random and weird, Memories, Hypothetical, About us and Deep. Start with the funny questions or the random and weird ones when you want fun questions to ask friends on a night in, a road trip or in the group chat, and save the deep questions for when the evening slows down. The juicy ones, gossip-level honest and never unkind, sit in About us and Deep. Each group runs from easy to harder, so you can stop wherever the evening wants to stop, and every question comes with a short note on what it tends to bring out.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Funny
What normal, everyday thing are you strangely bad at?
Why ask it
Friends will usually volunteer an answer on the person's behalf, which is half the entertainment. Whistling, folding a fitted sheet and telling left from right all come up, and nobody minds owning up to them.
Which childhood belief did you hold on to for an embarrassingly long time?
Why ask it
You get a glimpse of the logic each person ran on as a kid. Ask how they found out the truth, because the moment of discovery is usually better than the belief.
What's your most pointless talent, and will you demonstrate it right now?
Why ask it
The demonstration is the whole question, so do not accept a description. Ear wiggling and dial-up modem impressions are the standard, and anyone who refuses can be assumed to have lost the knack.
What did you pretend to understand for so long that it became too late to ask?
Why ask it
Covers everything from a card game's rules to a colleague's name. The phrase 'too late to ask' is what people recognize, and it gets a groan of solidarity.
What were you last told off for, and who did the telling?
Why ask it
A partner, a toddler, a librarian, a laminated sign. Being scolded as an adult is funny because the offense is usually tiny and the shame is out of all proportion. Ask whether they have reformed.
What ridiculous lengths have you gone to just to save a tiny amount of money?
Why ask it
Low stakes and easy to answer, so it suits the start of an evening. Get the numbers, because the arithmetic is the punchline: forty minutes across town for cheaper fuel rarely comes out ahead.
What's the laziest thing you've ever done to avoid a small task?
Why ask it
Everyone has engineered an elaborate workaround to dodge two minutes of effort. The answers are oddly flattering, since laziness at this level takes ingenuity.
What's the worst haircut you've ever had, and does a photo survive?
Why ask it
Home cuts and the one given by a parent at the kitchen table tend to win. If a photo exists the group is entitled to see it, though not to post it.
What food do you have your own method for eating, and who has asked you to stop?
Why ask it
Expect strong reactions and at least one person defending their method on principle. It works well at a table, where demonstrations are possible.
What did you put real effort into as a teenager that impressed absolutely nobody?
Why ask it
The band, the signature, the dance routine, the personal website. The effort is what makes it endearing in hindsight. Friends who knew each other back then should be allowed to testify.
What's the pettiest reason you've ever decided you didn't like a stranger?
Why ask it
Pettiness confessed is charming in a way that pettiness observed is not. Keeping it to strangers stops anyone from settling a real score.
What's the most awkward way you've ever said goodbye to someone?
Why ask it
These take ten seconds to tell, so the next person can try to top it straight away. The classics are 'love you' said to a delivery driver and a warm farewell followed by both people walking off in the same direction.
What compliment did you once receive that you later realized was an insult?
Why ask it
'You're so brave to wear that' and its relatives. The delay is the funny part, so ask how long it took to sink in and whether they have used the line on anyone since.
What's the worst gift you've ever had to act thrilled about?
Why ask it
Check first that the giver is not sitting in the circle. Then request a re-enactment of the face they made on opening it, since the acting is better than the gift.
What have you gone along with only because you were too polite to say no?
Why ask it
Politeness carried too far is funny because the teller could have left at any point and stayed anyway. Expect a two-hour sales pitch, a third helping, or a stranger's parrot held for much longer than agreed.
What's the most ridiculous thing you've ever cried about?
Why ask it
A commercial, a dropped sandwich, a cartoon animal. It lets people admit to being soft without anything heavy attached to it.
What did you do the last time you waved back at someone who was waving at the person behind you?
Why ask it
Nearly everyone has done it, so the whole room winces together. Turning the wave into a hair adjustment is the standard cover, and anyone who simply kept waving deserves some respect.
What's the most confidently wrong thing you've ever said in front of other people?
Why ask it
Friends who were present tend to remember it more precisely than the speaker would like. A mispronounced word counts, and so does a fact about sharks delivered with total authority to a full table.
What did you spend real money on and then use exactly once?
Why ask it
The bread maker, the gym membership, the inflatable kayak. Every one of these purchases came with a vision of a new life, so ask what the vision was and where the object lives now.
What did you expect to be a natural at, right up until your first attempt?
Why ask it
The story starts before the attempt, so find out what they told people on the way there. Skiing and karaoke account for a lot of these, along with flat-pack furniture built without the instructions.
Which search from your phone this week would need the most explaining if read aloud?
Why ask it
Limiting it to this week keeps answers fresh and mostly harmless. Let people describe the search instead of showing the screen, so nobody feels cornered.
Which harmless creature or noise in the night has sent you into a full panic?
Why ask it
Housemates and siblings make excellent witnesses, and their version is less flattering. Find out how far the response went: standing on the furniture is common, and sleeping at a friend's place because of one moth is not unheard of.
What do you still do exactly the way you did it as a small child?
Why ask it
Eating the filling first, jumping the last two stairs, keeping both feet under the blanket. Habits like these survive because nobody ever asks about them, so the answers come out with some surprise.
What lie did you tell as a kid that got far more out of hand than you planned?
Why ask it
Childhood lies escalate in a way adult ones rarely do: invented pets, fake injuries, imaginary cousins. Ask how long they kept it going.
How far have you gone to avoid saying hello to someone you recognized in public?
Why ask it
It rarely works cleanly, and the best versions end with the other person saying hello anyway. A faked phone call is the amateur move, while hiding in a shop for twenty minutes takes commitment.
What's the most embarrassing thing a parent or relative has done in front of your friends?
Why ask it
The dancing, the baby photos, the pet name shouted across a parking lot. If the friends in question are in the room, they will usually say they loved it, which is some comfort years too late.
What bet were you certain you'd win, and what did losing cost you?
Why ask it
Confidence is the key ingredient, and a stake is what makes the memory last. Look for the answer where they raised the stakes at least once before the facts arrived.
What's the most elaborate excuse you've ever given to get out of plans, and did it work?
Why ask it
Risky in a good way, since someone in the room may have been on the receiving end. Grant a general amnesty before anyone answers.
What's the most strongly worded complaint you've ever sent, and what was it about?
Why ask it
Told best by people with enough distance to find themselves ridiculous. Now and then someone still has the text of the letter to the airline or the review written at midnight, and a reading is in order.
What's the most dramatic exit you've ever made from a room, a job or a group chat?
Why ask it
Doors that bounce back open and resignation emails with a typo in the subject line belong here. Exits almost never go as rehearsed, and the gap between the intended effect and the result is the story.
What would your autobiography be called if your family got to pick the title?
Why ask it
Families keep a fixed, slightly unfair version of each of us. Under cover of a joke, the answer tells you what role someone played at home and how they feel about it.
What did you get in trouble for that truly wasn't your fault?
Why ask it
Old injustices stay remarkably fresh. Expect a full legal defense, and appoint the group as jury if the facts seem shaky.
Random and weird
What's the last thing you took a photo of, and why?
Why ask it
A camera roll is a fair record of what someone's days are made of. Expect a parking space number or a dog that wasn't theirs, and leave showing the photo optional.
What's the weirdest food combination you will defend to anyone?
Why ask it
Fries dipped in a milkshake, peanut butter on a burger, cheese with fruitcake. Someone will be horrified and someone else will ask to try it, and the question needs both of them.
What's the strangest place you've ever fallen asleep?
Why ask it
Quick enough for a group chat. The waking up is the better half of the story, especially on a bus that has reached the end of the line.
What phone number, password or jingle from years ago is still taking up space in your head?
Why ask it
The brain keeps a childhood landline number and an advert for a carpet shop while losing this morning's password. Push for the jingles, because the group will end up singing at least one of them together.
Which word do you hate the sound of, for no reason you can explain?
Why ask it
Saying it out loud to friends is a mistake a person makes exactly once. Expect to hear the word repeated back for the rest of the night, and possibly for years.
Who's the most famous person you've ever met or stood next to, and how did you behave?
Why ask it
The encounter is usually brief and the behavior is usually poor: staring, saying something odd, pretending not to notice. A minor celebrity makes a better story than a major one, because the group has to work out who it was.
If you could only eat food of one color for a week, which color would you pick?
Why ask it
Beige wins on comfort: bread, pasta, potatoes, most of a bakery. Green has the moral high ground and red claims pizza on a technicality, and friends will argue the technicalities for longer than seems possible.
What smell takes you straight back to one specific place?
Why ask it
Chlorine, a certain sunscreen, a grandparent's hallway. People tend to answer with a room and a year before they have finished naming the smell.
What piece of trivia have you been waiting years for a chance to use?
Why ask it
This is the chance. Somebody will dispute it, a phone will come out, and the argument over whether looking it up is allowed can outlast the fact.
What do you think your pet, or an animal you see most days, honestly thinks of you?
Why ask it
Cat owners answer with a level of self-criticism they would never accept from a person. Friends without pets can use a neighbor's dog or the pigeon outside the office, and that version is often the funnier one.
What do you take far more seriously than it deserves?
Why ask it
If the person can't think of one, their friends can, and the friends will be right. Board game rules and the correct way to pack a trunk are where a lot of dignity turns out to live.
What do you do without noticing whenever you're on the phone?
Why ask it
Most people only know because someone who lives with them pointed it out, so let the housemates answer first. Pacing the whole house is the common one, and tidying a drawer that didn't need it is the useful one.
What sound can you not stand, and what sound do you find oddly satisfying?
Why ask it
Chewing or squeaking polystyrene on one side, a new jar lid popping on the other. Be warned that somebody will immediately make the hated sound.
What's the weirdest thing you find relaxing?
Why ask it
Untangling necklaces, carpet-cleaning videos and reading an instruction manual from cover to cover all qualify. It costs nothing to admit, and it tells you what settles a friend down when they are wound up.
What's the most random thing a stranger has ever asked you?
Why ask it
Strangers pick people who look approachable, so the stories also show who in the group has that kind of face. Being asked to hold a ferret or stand in a wedding photo is the price of having it.
What have you found in a coat pocket, a library book or something second-hand that you still wonder about?
Why ask it
A stranger's shopping list, a single key, a train ticket from another country. A found object arrives with a mystery attached, and friends will happily invent the rest of it.
What did you once collect that made sense to nobody but you?
Why ask it
Childhood collections count: bus tickets, hotel soaps, rocks with a stripe through them. Find out where the collection is now and who made them get rid of it.
Which animal do you not trust, and what did it do?
Why ask it
Geese get named a lot, and not unfairly. There is usually an incident behind the grudge, often from childhood, told with a seriousness that makes it funnier.
What random skill would you like someone to teach you in a single afternoon?
Why ask it
A small skill is a more honest wish than a big ambition. If it is whistling with two fingers or shuffling cards properly, there's a fair chance someone present can teach it on the spot.
Which fictional world would you last the shortest time in?
Why ask it
Turning the usual question around swaps wishful thinking for an honest look at your own survival skills. Friends tend to agree with the verdict a little too quickly.
What have you seen a stranger do in public that you still can't explain?
Why ask it
Having no ending is what keeps it in the memory: the full dinner party laid out on a train platform, with nobody to ask. The group's job is to supply theories.
What's the strangest coincidence that has ever happened to you?
Why ask it
Meeting a neighbor on another continent, two friends who turn out to share a cousin. Coincidence stories invite friendly one-upmanship, so let it go around the circle more than once.
What sign have you seen that only exists because somebody once did something very strange?
Why ask it
Every oddly specific rule on a wall is the last line of a story nobody wrote down. The group's task is to reconstruct the incident, and the more specific the sign, the better the incident.
What superstition or small ritual do you keep up even though you know better?
Why ask it
People are a little sheepish about these, so admit yours first. A lucky pen or a refusal to put new shoes on a table is easier to own up to once somebody else has.
If you came back as a ghost, where would you haunt and how would we know it was you?
Why ask it
Hardly anyone picks revenge. The plans are mild and specific, like standing in a bakery all day or moving one person's keys, and the calling card each friend invents is often a habit the group already teases them for.
Which dream can you still remember in detail years later?
Why ask it
Other people's dreams are hard to listen to, so set a limit of one minute each. The ones carried since childhood are usually the oddest and the most worth the minute.
What have you said in your sleep, according to whoever had to hear it?
Why ask it
Reported by siblings, roommates and tent-mates, never by the speaker. Full sentences are rarer and better than mumbling, and nobody can be held responsible for the content.
What conspiracy theory have you invented about something completely trivial?
Why ask it
That one traffic light holds a grudge, that the office printer can tell when someone is in a hurry. Insisting on trivial keeps real politics out of the room, and the more evidence the person has gathered, the better.
What half-remembered film or TV scene from childhood have you never been able to identify?
Why ask it
A talking horse and a lighthouse, with no title and no year, is the kind of clue friends love. With a few phones in the room the mystery sometimes gets solved, which is a strange relief to witness.
What do you think about that you assume nobody else does?
Why ask it
Quite often another person in the group says they wonder about it too, and that small jolt of recognition is the reward. Where pigeons go at night is a fair place to start.
Memories
What did you beg your parents for as a kid and never get?
Why ask it
A dog, a trampoline, the cereal with the toy inside. It tells you what someone wanted before they cared what anyone thought. Ask whether they have bought it for themselves since.
What did your bedroom look like when you were ten?
Why ask it
An easy way into someone's childhood without asking about it directly. Listen for whether the room was shared, what was on the walls and what the window looked out on.
What film or show did you watch so many times as a kid that you can still quote it?
Why ask it
A favorite that got replayed for years says a lot about a household: who chose it, who was sick of it, which sibling did the voices. Ask for a line, and see whether someone else in the group can finish it.
What imaginary friend, secret game or made-up world did you have as a kid?
Why ask it
A sibling who was drafted into someone else's invented country can describe it from the other side, with complaints about the rules. The details people still remember, a flag or the name of an invisible horse, show how seriously it was taken.
What meal from your childhood would you love to eat once more, exactly as it was made?
Why ask it
The words 'exactly as it was made' point at the cook as much as the food. Be ready for the answer to turn tender if that person is no longer around.
What's the first thing you remember saving up for?
Why ask it
The object matters less than the weeks of wanting it. The first big purchase is often the first big letdown too, and people tell that part with real feeling.
What did the adults around you predict you'd grow up to be, and how close did they get?
Why ask it
A lawyer because they argued, a vet because they liked the dog. The prediction shows how a kid was seen at home, and the distance between it and their real life is often the better half of the answer.
What word or phrase did your family use that you later learned nobody else says?
Why ask it
Families invent names for the remote, for leftovers night, for a particular kind of bad mood. The discovery tends to happen in front of other people, and the embarrassment is part of the story.
What was the first music that felt like it belonged to you and not to your parents?
Why ask it
Taste is one of the first things people claim as their own. Ask how they found it, since the older sibling, the friend or the late-night radio show is part of the answer.
What sound from the home you grew up in would you recognize anywhere?
Why ask it
A particular door, a parent's keys, the furnace kicking on, a neighbor's dog. Sound memories arrive whole and oddly detailed. Good for quieter friends, who can answer in a sentence.
Which friend's house did you spend the most time at growing up, and what was different there?
Why ask it
Another family's house is often where a kid first learns that home could work differently: other food, other rules, another noise level. The answer also hints at what each person went looking for in a friend.
What did you think was normal about your hometown until you left it?
Why ask it
Friends who grew up in the same place will back each other up, and everyone else gets to be baffled. A festival for a vegetable or a roundabout with a nickname only looks odd from a distance.
What was the first thing you were allowed to do on your own, and how did it go?
Why ask it
People remember the route and the instructions in surprising detail, whether it was the walk to school or the first bus into town. The first taste of being trusted is the real subject.
What family trip went wrong in a way everyone still talks about?
Why ask it
Disasters age into the best stories. Notice who the hero and the villain are in the telling, since families tend to assign those parts permanently.
What's the most lost you have ever been?
Why ask it
Left open on purpose. The usual story involves a wrong turn or a foreign train station, but now and then someone takes it another way, and you should let them.
What was your hiding place as a kid, and what did you keep there?
Why ask it
Under the stairs, up a tree, the back of a closet. What went in there, whether snacks, a diary or contraband, shows what a kid thought was worth protecting. Not everyone had one, and the reason why is an answer too.
What job taught you something the hard way?
Why ask it
First jobs and bad jobs leave lasting rules about how to treat people. Ask what they do differently as a customer or a colleague because of it.
Which teacher or coach said something you still remember word for word?
Why ask it
A single sentence from an adult can steer a kid for years, in either direction. The person who said it has probably forgotten, which is the strange part.
What did you do as a teenager that you would be terrified to watch a teenager do now?
Why ask it
Rides accepted, roofs climbed, trips taken with no plan and no way to call home. The answer marks how far someone's sense of risk has moved, and friends who were there can usually add a detail the teller left out.
What small kindness from a stranger do you still think about?
Why ask it
These stories are short and people rarely get to tell them. The kind of help they remember usually says something about what they were short of at the time.
Which place from your past no longer exists the way you remember it?
Why ask it
It carries some weight, so save it for when the mood has already slowed down. A sold house or a field that became a parking lot can still be walked through in memory, and people will do it out loud if given the time.
Which summer would you relive from start to finish?
Why ask it
A whole summer asks for a period of life, not a single event. Pay attention to who else was in it, and whether they are still around.
When did you know, while it was still happening, that you would remember a moment for good?
Why ask it
Rare and specific: a moment of noticing your own life as it happens. Give it time, because people need a minute to find theirs and the first answer is rarely the real one.
Hypothetical
If you had to teach a one-hour class tomorrow with no preparation, what would it be on?
Why ask it
Finds the thing each person knows cold, which is often not their job. Friends are regularly surprised by the answer, and that surprise is worth a follow-up.
If someone else paid for one full-time helper, like a cook, a driver or a tutor, who would you hire?
Why ask it
The choice is a fair map of where someone's week leaks time, or of what they wish they were better at. Ask what they would do with the hours it freed up.
If you could be excellent at one sport you've never tried, which would you choose?
Why ask it
People pick for the lifestyle as much as the sport: the mountains, the team, the solitude. Have them describe a Saturday and you will hear which.
If you had to choose a new first name today, what would you go by?
Why ask it
Some people have had an answer ready since childhood and some are appalled by the idea. Both reactions tell you how they feel about the name they have.
If you had to wear one outfit every day for a year, what would it be?
Why ask it
Some people have been privately wishing for this rule. The outfit shows whether comfort, pockets or looking put together comes first, and friends will say they could have predicted it.
If you had to give up your phone for a month, what would you struggle with first, and what would you not miss?
Why ask it
The first half gets practical answers: maps, the alarm, the bank. The second half is the interesting one, because what someone would be relieved to lose is often what they already suspect takes too much of them.
If you were handed the keys to any building for one night, which building, and who is coming with you?
Why ask it
A museum, a stadium, a department store, their old school. The building shows what they are curious about, and the guest list shows who they think would make it fun, which in this company is a compliment worth hearing.
If this group had to enter a competition as a team next month, what would we have the best chance of winning?
Why ask it
The debate turns into an inventory of what each friend is good at, which is a pleasant thing to overhear about yourself. Somebody always suggests a quiz, and somebody else points out the gaps in what the group knows.
If you had to give up either music or movies for good, which one goes?
Why ask it
A forced choice with no right answer, which is what makes groups argue about it happily. Ask what they'd miss most on an ordinary weekday, not in theory.
If you could pause time for one hour a day while everyone else stayed frozen, what would you use it for?
Why ask it
Sleep, reading, finally answering messages. The hour people invent is usually the one they feel their life has taken from them, so listen for the complaint inside it.
If you could bring back one thing that has been discontinued, what would you revive?
Why ask it
People answer fast and with real feeling, whether it is a snack, a shop that closed or a bus route. When someone else in the group remembers it too, the answer turns into shared mourning.
If you could wake up fluent in one more language, which one, and who would you talk to first?
Why ask it
The second half does the work. A friend who names a grandparent or a neighbor instead of a country has told you who they wish they could reach.
If you could watch any one event from history without being able to change it, what would you pick?
Why ask it
Ruling out interference removes the hero answers and leaves pure curiosity. Some people choose a world event, and others pick the day their grandparents met.
If you had to live in another decade at the age you are now, which one would you take?
Why ask it
Keeping their current age forces people to think about daily life, not nostalgia. Expect someone to bring up dentistry, and expect them to have a point.
If you could get one honest statistic about your own life so far, what would you ask for?
Why ask it
Hours spent looking for keys, close calls they never noticed, how many people have had a crush on them. The pick shows whether someone is more curious about wasted time, narrow escapes or what others think of them.
If a documentary crew followed you for a month, what would turn out to be the main plot?
Why ask it
Asks people to see their own life from outside. The subplot they mention with a laugh, the feud with a neighbor or the endless house project, is often the truth.
If you had to be famous for something, what could you stand being famous for?
Why ask it
The phrase 'could stand' assumes fame is a burden, which changes the answers. Many people pick something narrow and respected over something big and loud.
If you had to move to a small town where you knew nobody, what would you do in your first month?
Why ask it
Shows how each person builds a life from nothing: join a team, find a cafe, stay in and wait. Useful knowledge about a friend, especially one who may move someday.
If your bills were paid for a year but you weren't allowed to work or study, how would you fill it?
Why ask it
Removing work and school takes away the respectable answers. Some people light up and some look faintly alarmed, and the alarmed ones are worth asking about.
If you could have a standing monthly dinner with someone from any profession to learn how it really works, which profession?
Why ask it
Curiosity about a field is often a quiet signal of a road not taken. Ask whether they ever considered it, and what stopped them.
If you could read a truthful review of yourself written by anyone you've ever met, whose would you read?
Why ask it
An ex-friend, a first boss, a parent. Whoever they name is someone whose opinion is still unfinished business, so tread lightly with follow-ups.
If you could keep only one year of your life in full detail, which year would you save?
Why ask it
Harder than it sounds, since the happiest year and the most important year are often different. Ask which of those two they were choosing by.
If you could see how one path you turned down would have gone, which would you look at, or would you rather not know?
Why ask it
The option to pass matters. Those who take it usually have a thoughtful reason, and those who don't will name the decision they still turn over: the job, the city, the person.
About us
When did each of us go from someone you knew to an actual friend?
Why ask it
Best with friends who met as adults or near-adults. The turning point is often small, a shared bad day or a long car ride, and the two people involved may name different moments, which is worth comparing.
What did you think of each of us the first time we met?
Why ask it
First impressions between friends are usually wrong in an entertaining way: too loud, too serious, certain not to get along. Stick to impressions that have since been overturned, so the honesty ends as a compliment.
If everyone in this group had a job title within the friendship, what would mine be?
Why ask it
Head of logistics, minister of snacks, chief worrier. Asking about yourself keeps it generous, and the titles have a way of sticking for years.
Who in this group would cope best if we were all stranded somewhere with no signal?
Why ask it
A comparison question that stays kind, because competence is a compliment. It gets sharper if you also ask who would be first to suggest eating the supplies.
What pointless debate does this group keep coming back to, and which side are you on?
Why ask it
How to load a dishwasher, the right route to the coast, whether that one film was any good. A recurring argument is part of how a group knows itself, and nobody gets hurt reopening it. Let the debate run for a bit.
Which of our inside jokes has lasted the longest, and does anyone remember how it started?
Why ask it
Origin stories for inside jokes are often disputed, and sorting out the true version is the enjoyable part. Anyone who joined the group later gets some useful history.
What story about one of us do you tell to people outside this group?
Why ask it
Everyone is a character in their friends' anecdotes and seldom finds out which one. Ask the subject's permission before telling it again here, since they may never have heard their own legend.
What's the worst idea one of us ever talked the rest into?
Why ask it
The shortcut, the camping trip in March, the matching outfits. Blame gets handed out quickly and cheerfully, and the guilty party will usually insist it was a good plan badly carried out.
What plan do we keep saying we'll make and never do?
Why ask it
Every group has the trip, the dinner or the hike that lives permanently in the future. Asking out loud sometimes ends with a date in the calendar.
What's the most 'us' thing that has ever happened to this group?
Why ask it
You are asking for the story that would explain you all to a stranger. When several people name the same event, you have found the group's founding myth.
What's the most out-of-character thing any of us has ever done?
Why ask it
The group remembers these because they broke the pattern: the careful one who quit on the spot, the quiet one who took the microphone. The person concerned tends to insist it wasn't out of character at all.
Who here gives the most useful advice, and who gives the most entertaining advice?
Why ask it
Two categories means two people get a compliment, and the entertaining one is arguably the higher honor. Expect the nominees to object.
Which of us is the worst at keeping a secret, and how do we know?
Why ask it
Juicy without being unkind, as long as the nominee gets to mount a defense. Leave the secret itself out: the story is about the leak, not about what leaked.
What do you now love that someone in this group had to talk you into?
Why ask it
A band, a food, a sport, a whole city. Friends rub off on each other without noticing, and hearing that your nagging became someone's favorite thing is a quietly large compliment.
What phase did this group go through that you're glad is over?
Why ask it
Teasing the group as a whole is safer than teasing any one member. Every group has an era to choose from, whether it was the terrible apartments or the year everyone took up running.
What's the best piece of gossip about yourself that we somehow haven't heard?
Why ask it
The only person exposed is the one telling it, which is what keeps a juicy question friendly. Friends hold back a surprising amount simply because nobody asked, such as a brush with fame or a job that lasted a single day.
What have you never admitted to us about a time we all remember?
Why ask it
Who really broke the lamp, who was awake and heard everything, who secretly hated the trip. Enough time has usually passed for it to be forgiven, and the confession rewrites a story the group thought it knew.
What would each of us be the right person to call for?
Why ask it
Going person by person avoids ranking anyone and tells each friend what they are trusted with, whether that is a flat tire, a breakup or a second opinion on a lease.
What do you think an outsider notices first about how we talk to each other?
Why ask it
Groups develop a style, whether interrupting, teasing or talking in references, that is invisible from inside. Partners who joined the group later can answer with authority.
What do you do for this group that you suspect nobody notices?
Why ask it
The planner may be tired of planning, and the one who always checks in may wonder who would check on them. It gives quiet work a hearing, and the right response is thanks, not a defense.
How are you different with us compared with your family or the people you work with?
Why ask it
With old friends, people are often louder, sillier or more honest. Occasionally someone says they hold back here too, and that is worth hearing without getting defensive.
What does this group give you that the other people in your life don't?
Why ask it
Often it's small and unglamorous: a place to be silly, people who remember the earlier versions of you, advice with no agenda. Knowing what each person comes here for tells you what to protect when life gets busy.
What's something you were nervous to tell us that turned out fine?
Why ask it
A look back at a moment when the group passed a test without knowing it. Hearing it also tells everyone that the next hard thing can be said here too.
When have you felt most looked after by this group?
Why ask it
The answer is often something the others barely remember doing. Let each person finish their story before anyone waves the credit away.
What have you wanted to thank one of us for but never got around to?
Why ask it
Gratitude between friends tends to go unsaid because it feels awkward in the moment. A question gives everyone permission, so expect a short silence first.
What do you hope we're all still doing together when we're old?
Why ask it
Card games, the same campsite, complaining about the same things. It makes a warm way out of a heavy stretch, because the question takes it for granted that the friendship lasts.
What would you want us to do if you went quiet for a few weeks?
Why ask it
One friend wants a knock on the door, another wants a no-pressure message and patience. Knowing the difference in advance is about as useful as anything a group can learn.
What's one way you'd like us to be better at showing up for each other?
Why ask it
Phrased about 'us' so that nobody is on trial. The requests are usually modest: reply sooner, ask twice, come to the boring events as well as the good ones.
Is there a subject we avoid as a group, and should we keep avoiding it?
Why ask it
Reserve this for a group on firm footing. Sometimes the avoided topic is money or a past falling-out, and sometimes the honest answer is yes, leave it alone.
Deep
What compliment has stayed with you the longest?
Why ask it
Praise sticks when it lands on something a person wasn't sure about in themselves. Notice who gave it, because it's rarely the person you'd expect.
What has gone well for you this year that you've held back from telling people?
Why ask it
Good news gets edited out of conversation for fear of sounding smug, especially around friends who are having a harder time. This gives it a sanctioned minute, and the group should resist making a joke of it.
Which old worry of yours looks smallest from here?
Why ask it
Hearing everyone's list of expired worries, the grade, the haircut, what one particular person thought, makes the current ones look a little more temporary.
When did you last feel properly proud of yourself?
Why ask it
The word 'properly' rules out the polite answer about work. The real one is often small and private, like keeping their temper or finishing something nobody asked for.
What did you once find embarrassing about yourself that you now quite like?
Why ask it
A laugh, an accent, an obsessive hobby. It tracks the distance between wanting to fit in and being comfortable, and people tend to enjoy measuring it.
What piece of advice did you ignore that turned out to be right?
Why ask it
Find out who gave it and whether they ever learned they were right. There is often an overdue acknowledgment hiding in the answer.
What have you changed your mind about because of a friend?
Why ask it
The story is usually about watching how someone lived, not about losing an argument to them. If the friend is in the room, they often had no idea they changed anything.
What have you judged someone for and later done yourself?
Why ask it
Moving back in with parents, going back to an ex, becoming the person who talks about their dog. It's a confession with a punchline built in, so it can be asked before the mood has fully turned serious.
What do you need in a day now that you happily went without a few years ago?
Why ask it
Shows how someone's idea of enough has shifted. The details they include, such as a quiet morning or an hour when nobody needs anything from them, say a lot about what currently wears them out.
What part of your personality did you have to grow into?
Why ask it
Some traits arrive late: confidence, patience, the ability to say no. It works well with friends who knew the earlier version and can confirm the change.
Which of your parents' traits do you see in yourself, and how do you feel about it?
Why ask it
People tend to notice mid-sentence, when a parent's phrase comes out of their own mouth. Some answer with pride and some with alarm, and the same trait can produce either.
What unspoken rule of friendship do you hold people to?
Why ask it
These rules stay silent until somebody breaks one, so hearing them in advance can spare a grudge or two. Expect the group to split between friends who count birthdays and replies and friends who think a year of silence changes nothing.
Which fear has shrunk as you've gotten older, and which one has grown?
Why ask it
The pairing keeps it balanced and honest. Fears about embarrassment often shrink, while fears about time and the people they love move in to take their place.
Which earlier version of you do you miss?
Why ask it
Not the younger face but the habits: reading a book a week, dancing without thinking about it, phoning instead of texting. Old friends may say that version has not gone as far away as the speaker thinks.
What do you need more of right now: rest, change, company or a challenge?
Why ask it
Four options make it easy to answer quickly and truthfully. Follow with 'what would that look like this month?' and you may be able to help.
What do you wish you were braver about?
Why ask it
Usually something social and not physical: saying no, asking someone out, showing people the thing they made. Ask what the smallest brave version would look like, and offer to be there for it.
Who from your past would you like to run into, and what would you want them to notice?
Why ask it
What they want noticed is what they are proudest of, or what they still feel they have to prove. The two are easy to tell apart once you hear whether they picked an old friend or a teacher who wrote them off.
What has been taking up the most room in your head lately?
Why ask it
Gentler than asking what's wrong, and it lets the person decide how heavy to make it. If the answer is a worry, ask whether they want ideas or just an audience.
What do you know you need to do that you keep not doing?
Why ask it
The appointment, the phone call, the overdue conversation. Saying it to friends makes it a little harder to keep ignoring, so ask what would make it easier and whether they want a reminder or to be left alone.
What's something you've never told your parents?
Why ask it
Mostly harmless: the party, the dented car, the real reason for switching courses. Now and then the answer is heavier, so let each person choose the size of their secret.
What rumor or wrong impression about you were you never able to correct?
Why ask it
Schools and small workplaces are where these get made. Setting the record straight in front of friends, even years late, has a satisfaction of its own, so let them tell it in full.
What part of your life do you tidy up when you describe it to other people?
Why ask it
Juicy in the honest sense, and pointed at yourself and not at anyone else. It only works if the asker goes first with something real: the job that sounds better than it is, or the relationship summarized as 'fine'.
What decision of yours looked wrong to everyone else and right to you?
Why ask it
Quitting, moving, staying. The story shows how much outside approval someone needs to act, and whether they would make the same call again.
What's the most honest thing anyone has ever said to you, and how did you take it?
Why ask it
It usually stung. Ask how long passed between hearing it and admitting it was fair, and whether the two of them are still in touch.
What did you expect to have figured out by now that you're still working on?
Why ask it
Hearing a friend admit it tends to relieve everyone else at the table, whether the subject is money, sleep or what to do with a working life. The answers often mix humor with a little grief for the plan that didn't happen.
What do you want that you've been pretending not to want?
Why ask it
Pretending is a hedge against disappointment. Saying the wish to friends, whether it is a promotion, a relationship or a move back home, is a low-risk first attempt at owning it.
What are you doing mostly because someone else expects it?
Why ask it
The answer isn't always a complaint. Some people look at the degree, the career or the weekly phone call, decide the expectation is fair and say so, and that is a kind of clarity too.
Whose life do you catch yourself comparing yours to, and what is it they have?
Why ask it
The words 'catch yourself' let people admit to envy without defending it. Answers tend to be about ease more than possessions: someone's calm, their free weekends, how sure they seem. Naming the person is optional.
What would you do differently if you were certain nobody would judge you for it?
Why ask it
Points at the gap between the life someone has and the one they'd choose. The changes are often small, like dressing differently, quitting a committee or singing in public.
Where do you feel most like an outsider?
Why ask it
At family gatherings, in certain meetings, sometimes in a room full of people they like. Listen for whether it's about where they come from, what they earn or what they believe, and don't tell them they shouldn't feel it.
Which lost friendship do you still think about?
Why ask it
Friendships seldom get a proper ending, so this may be a story nobody has heard. Let the person decide whether it was a drift or a break, and don't press on whose fault it was.
What was the loneliest stretch of your life, and what got you out of it?
Why ask it
How they got out names what the person reaches for, and what a friend could offer next time. The stretch itself is often an ordinary one, like the first year in a new city, which is why nobody noticed.
What are you still angry about that you suspect you should let go of?
Why ask it
A heavy one, so let people answer in outline without names or details. The word 'suspect' matters: it leaves room for someone to say they are not ready to, and that is an acceptable answer.
What would you tell us if you knew nobody here would try to fix it?
Why ask it
Ask this late, in a small group, and answer it yourself first. Friends often hold something back because they expect advice when what they want is an ear. The condition in the question is a promise, so keep it: the only correct reply is attention.
How to use these with a group of friends
Practical guidance for the conversation itself
Setting it up
Pick the moment, not the occasion
Questions land when people are already settled: a long drive, the slow part of dinner, the walk home. Announcing a question night makes everyone perform. Slipping one in while something else is happening works better.
Start in the shallow end
Open with two or three from Funny, Random and weird or Hypothetical, even with old friends. The light ones are not a warm-up to be endured. They establish that any answer is welcome, which is what makes the later questions possible.
Answer first when it is a hard one
If you ask something from About us or Deep, go first and give a real answer. A group matches the depth of the first answer it hears, so a throwaway from you gets throwaways back.
Let people pass without a reason
Say once at the start that anyone can skip anything, no explanation needed. A pass that costs nothing keeps people in the game. A pass that gets questioned teaches everyone to give safe answers.
Keep the juicy ones about the people in the room
The juicy questions in About us and Deep ask for honesty about yourself and about the group. They are not an invitation to discuss someone who is not there. If an answer starts turning into gossip about an absent friend, steer it back to the person answering.
Ways to run it
One question, everyone answers
- 1Pick one question and read it out.
- 2Go around the group, with the asker answering last.
- 3Allow one follow-up per answer, from anyone.
- 4Move on when the follow-ups have turned into a different conversation, which is the point.
Pass the phone
- 1Open the list on one phone and hand it to the person on your left.
- 2They scroll, choose a question and choose who answers it.
- 3Whoever answered takes the phone and picks next.
- 4Nobody may pick the same person twice in a row.
One tag per course
- 1Assign a tag to each stage of the evening: Funny while people arrive, Memories with the food, About us once the plates are cleared.
- 2Ask only one or two per stage.
- 3Save Deep for whoever stays late, and only if they want it.
The group chat version
Post a single question on a quiet weekday and let the answers trickle in. Random and weird, Hypothetical and Memories work best in text. About us and Deep lose their tone in a chat and are better kept for when you can see faces.
When it goes sideways
One person answers everything
Every group has a talker. Switch to going around in a fixed order, or have the person who just answered choose who goes next. It evens things out without anyone being told to be quiet.
An About us question starts to sting
Questions that compare friends can land badly on someone having a rough month. If an answer hurts, say so plainly, drop the rest of that question and go back to a Funny one. Do not make the hurt person explain.
Someone shares more than the room expected
Do not rush to fix it or top it with your own story. Thank them, leave a beat, and ask whether they want to say more or move on. What was said stays in the group: agree on that before you start, not after.
It starts to feel like an interview
That usually means too many questions too fast. One good question can carry half an hour. If the conversation has wandered somewhere better, put the list away, because it has done its job.