Would You Rather Questions for Teens
Would you rather questions for teens in middle school and high school, about twelve to eighteen, written for a sleepover, a classroom or youth group, or a long drive with a parent. They are sorted into Funny, School, Friends and phones, Fame and money, Hard choices and The future, and each group starts light and gets harder. Every question carries a short note for whoever is running the game, all of it is clean, and nothing asks anyone to share something private in front of the group.
One at a time · 01 of 114
Funny
“Would you rather have your parents pick your outfit every day for a month or pick your profile picture for a whole year?”
Why ask it
Clothes come off at night and the picture stays up, which is the math to listen for. If a parent is playing, have them describe the outfit they would choose.
Shuffle these in the Would You Rather Generator.
The questions
Each question, and why to ask it
Funny
Would you rather have your parents pick your outfit every day for a month or pick your profile picture for a whole year?
Why ask it
Clothes come off at night and the picture stays up, which is the math to listen for. If a parent is playing, have them describe the outfit they would choose.
Would you rather begin every sentence with "breaking news" or end every sentence with "allegedly"?
Why ask it
Make the chooser keep it up for the next three turns. "Allegedly" usually gets the bigger laugh, because it makes every plain statement sound like a confession.
Would you rather eat only cafeteria food for a year or only gas station snacks for a year?
Why ask it
It doubles as a review of the cafeteria. Let them name the single lunch that would make the year survivable, then the gas station item they would be sick of by week two.
Would you rather wear the school mascot costume to every class for a week or have the mascot silently follow you to every class for a month?
Why ask it
People who hate attention often work out that the costume is the better hiding place, since nobody can see who is inside. Have the other side describe what the mascot does while they are at their locker.
Would you rather have a ringtone that is your own laugh at full volume or one that is a parent shouting your full name?
Why ask it
Everybody knows exactly how their full name sounds when they are in trouble, so ask for a demonstration. The laugh pickers have to do theirs too.
Would you rather have your most-played song of the year announced at a school assembly or have it play out loud every time you open your locker?
Why ask it
Everyone has a most-played song they did not choose on purpose, and most already suspect what theirs is. Let people volunteer the title and do not press anyone who would sooner keep it.
Would you rather be chased around the gym by one goose the size of a school bus or by a hundred school buses the size of a goose?
Why ask it
A twist on an old internet argument, and it works the same way: people start drawing up tactics at once. Give each side thirty seconds to explain the escape plan. The single giant goose is scarier than it sounds.
Would you rather rap every answer you give in class or sing every order you place at a restaurant?
Why ask it
Class happens daily and restaurants do not, and the quick ones spot that. Anyone who picks rapping owes the group one bar about this game.
Would you rather have your driver's license photo taken mid-sneeze or your yearbook photo taken mid-yawn?
Why ask it
One photo gets shown to strangers for years and the other sits on your classmates' shelves forever. Middle schoolers with no license in sight usually protect the yearbook.
Would you rather be stuck in an elevator for three hours with your principal or with a toddler who has just learned the word why?
Why ask it
Most groups take the toddler, on the grounds that a toddler cannot write anyone up. Ask the brave ones what they would say to the principal once the weather had been covered.
Would you rather have a backpack that screams when you unzip it or shoes that applaud with every step you take?
Why ask it
The backpack is a few awful seconds each class period and the shoes never stop. Ask which one gets them sent to the office first.
Would you rather wake up every school day to your principal reading the morning announcements or to your gym teacher blowing a whistle?
Why ask it
The whistle is over in a second and the announcements run all the way through the lunch menu. Whoever picks the principal delivers tomorrow's announcements in their most official voice.
Would you rather laugh like a movie villain every time you get an answer right or gasp out loud every time someone else does?
Why ask it
Acting it out is required. The villain laugh is the popular pick right up until someone points out that it would go off in the middle of a silent test.
Would you rather have a parent who chaperones every school dance and actually dances or one who comments on every one of your posts in full paragraphs?
Why ask it
A dancing parent is over by ten o'clock and a paragraph under a post is there for good. Parents who are playing should not announce which one they would enjoy more, though they will.
Would you rather have every photo taken of you this year include a photobombing pigeon or have your eyes closed in all of them?
Why ask it
The pigeon gets funnier the longer anyone thinks about it: picture day, the team photo, the passport. Eyes-closed people are choosing ordinary over memorable, which is a fair pick.
Would you rather keep a nickname given to you by your gym teacher or one given to you by a five-year-old cousin?
Why ask it
Have each person guess what their nickname would be before choosing. Gym teacher names tend to be a last name shouted across a field, and the cousin's could be anything at all.
Would you rather have your life turned into a musical where the songs start without warning or a reality show where you record a confessional after every argument?
Why ask it
Theater kids answer before the sentence is finished. For everyone else, ask what the first song would be about, or which small argument, the dishes or the front seat, would get the longest confessional.
Would you rather only whisper at concerts and games or only shout in libraries and movie theaters?
Why ask it
One rule takes away your loudest moments and the other wrecks everyone else's quiet ones. Underneath, it asks whether they would sooner miss out or be a nuisance.
Would you rather read minds for one school day or be invisible for one school day?
Why ask it
The two oldest powers in the game, cut down to a single Tuesday. Find out where the invisible ones go at lunch and which class the mind readers would sit in. Mind readers tend to change sides once someone mentions hearing what a teacher thinks of the homework.
Would you rather wave back at someone who was waving at the person behind you once a week or trip going up the stairs in front of a crowd once a month?
Why ask it
Small humiliations that everybody has lived through, so stories arrive on their own. Tell yours first if the group is slow to start.
School
Would you rather go to school in pajamas every day or in full formal wear every day, no exceptions?
Why ask it
Comfort wins most rooms, but nearly every group holds one person who has been waiting for an excuse to wear a suit. Ask the formal crowd what they would put on for a Monday.
Would you rather run the mile in gym every day or square dance in gym every day?
Why ask it
Athletes are stunned that anyone would choose the dancing, and that disbelief is most of the fun.
Would you rather have a locker that jams every single time or an assigned seat in the front row of every class?
Why ask it
Back-row regulars take the jammed locker without thinking, so ask what exactly they would miss about the back.
Would you rather have unlimited hall passes or unlimited extensions on due dates?
Why ask it
Procrastinators jump at the extensions, and somebody usually admits that with no deadlines at all nothing would ever get handed in. Hall pass people should say where they would go.
Would you rather have a substitute every day for a month or the strictest teacher in the building for a week?
Why ask it
It sounds one-sided until someone remembers that a month of substitutes means a month of worksheets and a test at the end of it. Teachers who run this in class tend to get very honest answers.
Would you rather start school at 6 a.m. and be done by noon or start at noon and stay until 7 p.m.?
Why ask it
Morning people and night owls sort themselves in seconds. Push on the details: practice, a job, dinner, and what is left of the evening on the late plan.
Would you rather take a short quiz every Monday or one giant final that counts for the whole grade?
Why ask it
People who cram defend the final, and people who already dread Sunday nights want nothing to do with a Monday quiz. A teacher who opens class with it gets a free poll on how the next unit should be graded.
Would you rather present first, before you have seen anyone else go, or last, after watching every good idea get taken?
Why ask it
Going first means it is over by 9:05, and going last means an hour of rewriting your opening in your head. Most people know their answer from experience, so ask for the presentation that taught them.
Would you rather do every group project alone or always work with partners the teacher picks?
Why ask it
Whoever picks alone has carried a group before and will tell you about it. Keep the story to what happened and leave out who the partners were.
Would you rather give a ten-minute speech to the whole school or take a ten-page test that only the teacher will ever see?
Why ask it
Do not rib the test takers: plenty of confident people would write twenty pages to stay off that stage. The speech side can prove it by giving their first sentence now.
Would you rather have the lead in the school play or run the lights and sound and never be seen?
Why ask it
Neither job is the lesser one, and crew kids will say so loudly. Ask each side what would go wrong on opening night without them.
Would you rather be the best player on a team that loses every game or ride the bench on a team that wins the championship?
Why ask it
Anyone who plays a sport, or an instrument in a band, has a real answer and probably a real season in mind. Ask whether the trophy would feel like theirs. Bench sitters who say yes should be believed.
Would you rather have your favorite subject taught by a teacher you cannot stand or your worst subject taught by the best teacher in the school?
Why ask it
It asks whether the subject or the person makes a class. With a classroom group, keep it hypothetical and name no actual teachers.
Would you rather eat lunch at a different table every day for a year or at the same table in the same seat until graduation?
Why ask it
Students know the cafeteria has more unwritten rules than any classroom. Listen for who finds a new table every day exciting and who finds it exhausting.
Would you rather learn everything at home from videos at your own speed or in a classroom with friends at the teacher's speed?
Why ask it
Many students have tried some version of both and hold firm views. The follow-up that matters is what they would really do with the time saved at home.
Would you rather give up summer break and never have homework again or keep summer and get double the homework?
Why ask it
Do the math out loud with them: ten weeks off against every school night of the year. The vote is often closer than the first reactions suggest.
Would you rather have open-note tests forever but no phone anywhere on campus or keep your phone and never see a study guide again?
Why ask it
A fair test of what a phone is worth during the school day. People who say they barely touch theirs at school have to back it up with this choice.
Would you rather have every grade you earn posted in the hallway or not be told any of your grades until graduation?
Why ask it
Strong students do not always pick the hallway, and their reasons are worth hearing. Nobody has to say what their own grades are in order to answer.
Would you rather redo sixth grade knowing everything you know now or skip straight to senior year knowing nothing extra?
Why ask it
Going back means being the wisest twelve-year-old alive, and it also means doing middle school twice. Ask what they would do differently on the first day.
Would you rather switch schools in the middle of the year and start fresh or stay where you are with everyone remembering everything?
Why ask it
Take this one slowly. Someone in the room may have been the new kid, or may badly want a clean start, and neither should have to explain.
Friends and phones
Would you rather lose your phone for a month or lose your bedroom door for a month?
Why ask it
The pause before the answer says how close the call is between being reachable and being left alone. Parents asking this in the car should promise not to treat it as a menu.
Would you rather have the newest phone with a cracked screen and unlimited data or a flawless one that only works on Wi-Fi?
Why ask it
Whoever picks the cracked screen has probably been living with one for months and can report that it is fine.
Would you rather only be able to use your phone standing up or only be able to use it outdoors?
Why ask it
A rule question, so the loophole hunters wake up: does a porch count, does leaning count. Decide the rulings as a group and stick to them.
Would you rather have a phone from 2005 that never breaks or the latest model that you share with a parent?
Why ask it
Explain what a 2005 phone could do: calls, slow texts and one game about a snake. Sharing still loses in most rooms.
Would you rather have your phone die at three every afternoon or get no signal anywhere inside your own home?
Why ask it
The answer tells you where someone's social life really happens, on the way home or behind a closed door. Anyone with practice until six takes the dead battery without blinking.
Would you rather lose every playlist you have ever made or every saved game you have ever played?
Why ask it
Gamers and music people each think the other loss is nothing. Have them count it up: a playlist added to since sixth grade against a save file with two hundred hours in it.
Would you rather text and never call or call and never text for the rest of high school?
Why ask it
Adults assume every teenager picks texting, and it is often true. Still, ask about the last time one call fixed what twenty messages could not.
Would you rather be left on read by your best friend or get a reply that just says "k"?
Why ask it
Expect a serious debate about which one means more trouble, and let the group settle what "k" is supposed to mean. Keep it to the general case and away from anybody's actual chat.
Would you rather have to like every post you scroll past or never be able to like anything again?
Why ask it
One makes you look as if you approve of everything and the other as if you approve of nothing. Ask which friend would notice first.
Would you rather post one photo a day picked at random from your camera roll or never post anything again?
Why ask it
People run through their camera roll in their heads before answering, and the faces they make are the entertainment. Nobody has to show the screenshot folder.
Would you rather be tagged in every unflattering photo taken of you or never appear in a single photo with your friends?
Why ask it
Ask them to picture the album from this year ten years on, and which version they would want to find: the bad angles or the gap where they should be.
Would you rather have your friends see your location at all times or have your parents see it at all times?
Why ask it
Plenty of families and friend groups already share locations, so this is less hypothetical than it sounds. A parent asking should listen to the reasons and argue with none of them.
Would you rather have screen time capped at one hour a day or unlimited time with the total shown to anyone who asks?
Why ask it
It works best when the adults answer too, since their totals are rarely better.
Would you rather accidentally send a text about your crush to your crush or to your mom?
Why ask it
This is about the mistake and not the person, so nobody says who the crush is and whoever runs the game shuts down any guessing. Most rooms decide the mom is worse, because she will have follow-up questions.
Would you rather go to a party where you know nobody or stay home and watch everyone you know post from one you missed?
Why ask it
One is uncomfortable for an evening and the other stings from the couch. If an answer comes back with some feeling behind it, that probably happened last weekend, so do not dig.
Would you rather watch a movie you hate with all your friends or see the one you have waited a year for by yourself?
Why ask it
Is a thing still good if nobody shares it? Going alone without a second thought is rarer at fifteen than at thirty, so whoever picks it deserves the floor for a minute.
Would you rather have a friend who is hilarious and always an hour late or one who is a little dull and always shows up?
Why ask it
Most people have stood outside a movie waiting for the first friend and sat through a slow lunch with the second. The better follow-up is which one they would call on a bad day, which is often not the one they would invite to a party.
Would you rather plan every single hangout or never get a say in the plan?
Why ask it
Each friend group has one planner who is tired of it, and that person will be glad somebody finally asked. If two people claim the job, let them plan next weekend.
Would you rather have three close friends who have never met each other or one big group that does everything together?
Why ask it
Separate friendships give you room to be different people, and one group gives you a place to belong. Neither is the healthy answer, so do not present one that way.
Would you rather spend two weeks on vacation with your best friend's family or bring your best friend along on two weeks with yours?
Why ask it
Really a vote on whose family is easier to be around. Go lightly if a parent is in the car, and ask what the friend would never get used to at your house.
Would you rather apologize first every time, even when you are right, or wait for the other person every time, even if it takes a month?
Why ask it
Apologizing first buys peace and waiting protects pride, and most people already know which one they do. Keep current feuds out of it, especially with both sides of one sitting in the circle.
Fame and money
Would you rather get a hundred dollars today or a thousand dollars one year from today?
Why ask it
Nearly everyone waits for the thousand, so change the numbers until someone flips: five hundred today, or three years of waiting. The point where they switch is the interesting part.
Would you rather be paid for your grades or paid for your chores?
Why ask it
A negotiation dressed up as a game, and parents should know that going in. Ask what rate they think is fair. Then ask what should happen in a bad week.
Would you rather have a lifetime of free concert tickets or a lifetime of free flights?
Why ask it
Flights with no spending money get you as far as the airport, and tickets with no flights keep you local, so the planners start combining right away. Ask for the first show or the first destination.
Would you rather own the best sneakers in school and nothing else new for a year or a whole closet of average new clothes?
Why ask it
Swap sneakers for whatever this group cares about, a guitar or a gaming setup, and the question still holds: one great thing or plenty of fine ones.
Would you rather have a summer job that pays double where you work alone or one at normal pay with all your friends?
Why ask it
Anyone who has had a job answers from experience. Ask the ones who have not what the extra money would go toward, and whether it would be worth a quiet summer.
Would you rather have ten thousand dollars you must spend by midnight or ten thousand you cannot touch until you turn thirty?
Why ask it
Spenders start a shopping list and savers start working out interest in their heads. Ask the midnight crowd for their first three purchases in order.
Would you rather earn every dollar you spend from now on or get an allowance with a parent approving each purchase?
Why ask it
Earning it means nobody else gets a vote on what it buys, and for some that settles it. It often opens a real conversation about what they pay for themselves at the moment.
Would you rather win a car you are never allowed to sell or half of what it is worth in cash?
Why ask it
Fifteen-year-olds tend to want the car, and anyone already paying for things tends to want the cash. Let them choose first. Gas and insurance can come up afterward.
Would you rather split a million dollars evenly with everyone in your grade or keep ten thousand all to yourself?
Why ask it
The size of the school decides it, so do the division out loud: a grade of fifty beats the ten thousand and a grade of five hundred does not. Then ask whether a whole grade with money to spend is worth the difference.
Would you rather have a famous parent or a famous best friend?
Why ask it
Neither option makes you the famous one, which is the trick: it asks which shadow is easier to live in. A parent's fame shapes a childhood, and a friend's can change the friendship.
Would you rather have a million followers and nobody to sit with at lunch or five close friends and no account anywhere?
Why ask it
Five friends wins the vote in most rooms, so ask what would be hardest to give up about the million. Free stuff, being listened to and being invited places all come up.
Would you rather go viral once and be recognized for a month or build an audience slowly and never be recognized in public?
Why ask it
Anyone who makes videos or music already has a view on this, so start with them. The rest can say whether being stopped in a store sounds like a reward or a cost.
Would you rather be famous online for something embarrassing or brilliant at something that nobody ever sees?
Why ask it
Does attention count if it is the wrong kind? Ask whether the clip would still feel worth it at twenty-five, when it is the first thing a search for their name turns up.
Would you rather be a professional athlete for five years or a coach for forty?
Why ask it
It works for music and acting too, so switch the field for a group with no athletes in it. Have the five-year side say what they picture doing the year after it ends.
Would you rather star in a hit show at sixteen or create one at thirty-five?
Why ask it
The sixteen-year-old gets the fame while somebody else makes the decisions. Ask what they imagine that star is doing at thirty-five.
Would you rather write a hit song released under somebody else's name or keep your name on songs almost nobody hears?
Why ask it
Listen for whether the work or the recognition matters more to them. That carries over to far more than music: group projects, team wins, a joke somebody else repeats louder.
Would you rather win the lottery with your name in the news or win half as much and never tell a soul?
Why ask it
Twice the money, and every acquaintance knows about it. The follow-up is who they could not keep it from, and most people have one specific person in mind.
Hard choices
Would you rather never be embarrassed again or never be bored again?
Why ask it
Harder than it reads. Embarrassment stops people from trying things and boredom is what gets them started. Ask which one runs more of their week.
Would you rather be promised eight hours of sleep every school night or two free hours every afternoon with nothing due?
Why ask it
Tired groups answer fast. A parent may learn more from it than from asking outright how late anyone was up.
Would you rather give up music for a year or give up every screen that is not for schoolwork for a year?
Why ask it
The screens look like the bigger loss until someone pictures a bus ride, a workout and a bad day with no music. Give them a minute to walk through an ordinary Tuesday.
Would you rather say yes to every invitation for a year or no to every invitation for a year?
Why ask it
Homebodies and joiners both get a year of misery. Ask each side for the invitation they would dread most under their own rule.
Would you rather pause time for one hour a day or rewind the last ten minutes once a day?
Why ask it
The pause is for getting things done and the rewind is for taking things back. Which one a person wants tells you whether their days run short on time or long on regret.
Would you rather skip any conversation you are dreading or replay any conversation that went badly?
Why ask it
Do not ask which conversation they have in mind. The questions that work are whether a skipped one would only come back later, and whether a replay would really go better the second time.
Would you rather be great at one thing and bad at everything else or decent at everything and great at nothing?
Why ask it
A report card rewards the second answer, and the people picking the first will say that nothing else does. Have them name the one thing before they commit.
Would you rather be the most talented person in your grade or the hardest working?
Why ask it
Talent sounds better at fourteen. Ask which one they would want in a lab partner or a teammate, and the vote tends to move.
Would you rather be the oldest of five kids or the youngest of five?
Why ask it
Actual oldest and youngest children will argue from evidence about who had it easier, and only children get to referee. Middle kids can say which end they would trade for.
Would you rather know the answers to every test and forget them an hour later or study hard and remember half of it for life?
Why ask it
In finals week the first one is tempting, and saying so is the honest move, so make room for it. Then ask which class they would truly want to remember half of.
Would you rather win by cheating and never get caught or lose fairly with everyone watching?
Why ask it
As a bare question it is too easy, so name the stakes: a scholarship, a final, the last game of senior year. Then ask whether they could enjoy the win.
Would you rather spend a year answering every question your parents ask with the whole truth or every question your friends ask?
Why ask it
Small lies do steady work in both places: "I am on my way" at home, "no, the haircut looks great" at school. Have them weigh which year would cost more weekends and which more friendships. Nobody has to give an example.
Would you rather have your parents know everything you do or know nothing at all about your life?
Why ask it
A parent who asks this has to be able to hear "nothing" without taking it personally. The better follow-up is what the middle would look like.
Would you rather have total freedom with nobody to call when it goes wrong or strict rules and someone who always shows up?
Why ask it
The same trade as a curfew, stated plainly. The ones who pick rules are not being timid, and it is worth letting them say why before the freedom side piles on.
Would you rather quit something you are good at but no longer enjoy or keep going because people are counting on you?
Why ask it
For many teenagers this is a live decision about a sport, an instrument or a team. Listen without steering. Never bring the answer back later as leverage.
Would you rather tell a friend a truth that might end the friendship or stay quiet and watch them make the mistake?
Why ask it
Keep it abstract in a group, because somebody there may be on one end of this right now. A good follow-up is how they would want a friend to handle it with the roles swapped.
Would you rather know exactly what everyone at school thinks of you or never be able to find out?
Why ask it
Curiosity usually wins the first vote. Then ask whether they could walk into school on Monday the same way after reading the full list.
Would you rather forgive someone who never apologized or get the apology and stay angry anyway?
Why ask it
It separates what an apology is for from what forgiveness is for. A strong pick for a youth group with time to stay on it, and too heavy for the last five minutes of class.
Would you rather have one friend who knows everything about you or twenty who know only the version you show at school?
Why ask it
Underneath, it asks how much of a person goes to school each day. Ask what the twenty would be good for that the one is not, and leave what the one friend knows out of it.
The future
Would you rather speak five languages or play five instruments by the time you are twenty-five?
Why ask it
Both are things a person could really start this year, so it opens the subject of what comes next without anyone being asked for a plan. Ask which language or instrument comes first.
Would you rather get a car at sixteen that barely runs or wait until twenty for exactly the one you want?
Why ask it
Where the group lives decides a lot: city kids with buses shrug, and rural kids take anything with four wheels.
Would you rather ride in self-driving cars forever and never get a license or drive yourself everywhere and never be a passenger again?
Why ask it
Some teenagers count the days to a license and others would happily never get one. The second half means no napping on road trips, which changes a few minds.
Would you rather graduate knowing how to cook, budget and change a flat tire or with one extra year of your best subject?
Why ask it
Students have opinions about what school leaves out, and this lets them say so. In a classroom, collect the skills they would add to the list.
Would you rather take a year to travel before deciding anything or go straight to what comes next and finish a year sooner?
Why ask it
No particular path after high school is assumed, and it should stay that way when you ask. Listen for whether the year off sounds like freedom or like falling behind.
Would you rather move somewhere far away where you know nobody after high school or stay in your hometown with everyone you know?
Why ask it
Some people have been planning their exit since eighth grade and some cannot picture leaving. Both are fine. A parent should try to hear either one calmly.
Would you rather wake up tomorrow as a twenty-five-year-old with a job and rent or stay the age you are now for five extra years?
Why ask it
How someone answers shows how they feel about being their age right now. Follow up with what they think the twenty-five-year-old does on a Saturday.
Would you rather choose a career at eighteen and be locked in or have to change careers every five years, like it or not?
Why ask it
The second option is a comfort to anyone who has no idea yet what they want to do. Ask the locked-in side which career, and whether they would have named the same one two years ago.
Would you rather be your own boss and never be sure of next month's income or work for someone else and always know your paycheck?
Why ask it
A teenager with a weekend job already understands this trade. Ask what business they would start, and let the group poke holes in it kindly.
Would you rather live in a tiny apartment in a huge city or a big house an hour from the nearest anything?
Why ask it
The picture they describe after choosing, who lives there and what is outside the window, is better than the choice itself.
Would you rather be one of the first hundred people to live on Mars or the person at mission control who talks to them every day?
Why ask it
Ask the Mars volunteers who they would miss, and the mission control crew whether they would be jealous.
Would you rather live in a future where robots do every job nobody wants or one where every job is still done by a person?
Why ask it
A large question that suits a classroom or youth group with twenty minutes to spare. Have each side name one job they would hand over gladly and one they would keep for people.
Would you rather see one photo of your life at thirty or a list of the five people you will be closest to?
Why ask it
The photo shows a place and the things in it, and the list shows who stayed. Those who pick the list often hope to see a name they already know on it, and they do not have to say which.
Would you rather spend a day with your parents when they were your age or a day with yourself at the age they are now?
Why ask it
Good in the car, because the parent gets asked what they were really like at fifteen and has to answer. The other choice is a look at how things turn out, and some people would sooner not have it.
Would you rather know one thing that will go wrong in the next ten years or one thing that will go right?
Why ask it
Worriers want the warning and optimists want something to look forward to. Ask whether knowing the good thing early would spoil it.
Would you rather peak in high school or not hit your stride until forty?
Why ask it
Good for anyone having a rough year, because it says out loud that this is not the whole story. Adults in the room can add which age they would call their best so far.
Would you rather come back to your school in twenty years as a teacher or as the parent of a student?
Why ask it
Either way they end up back in the building, which gets a groan. Ask what they would change on their first day in charge, and what they would warn their own kid about.
How to play would you rather with teenagers
Practical guidance for the conversation itself
Setting it up
Let a teenager hold the list
The game goes better when the person reading is one of them. Hand over the phone or the printout, rotate the reader every few questions, and give the reader one power: choosing who has to explain their answer. An adult who reads every card turns a game into an interview.
Vote together, then argue
Have everyone answer at the same moment, before anybody explains. Left to answer one at a time, a group of teenagers waits to hear what the most confident person says and agrees with it. Once the split is visible, the smaller side makes its case first and the argument can run. Teenagers will defend a goose the size of a school bus for five minutes if nobody rushes them, and that argument is the part they remember.
Adults play too, and go last
An adult who only asks comes across as collecting information. Answer honestly, after they have, especially on the school and money questions. Being told you are wrong about hall passes is the price of admission.
Make passing free
Anyone can skip any question without saying why, and nobody guesses at the reason. Say that rule out loud before the first card. It costs nothing on the funny questions, and it is what makes the later ones safe to ask at all.
Pick the tag for the room
Funny and School need no warm-up and work with people who met an hour ago. Friends and phones and Fame and money get opinions going. Hard choices and The future are slower and better with a group that already trusts each other, so reach them late or save them for the car.
Four places it gets played
At a sleepover or a party
Sit in a circle and pass one phone. The reader asks, and on a count of three everyone points left for the first choice or right for the second. Whoever is in the minority has to defend it. Switch tags when the energy drops, and go back to Funny whenever a question lands badly.
In a classroom
Put one question on the board as students walk in and have them move to one side of the room or the other. Take one reason from each side, allow switching, and you have a five-minute warm-up that gets every student out of a chair and on the record. The School and Hard choices questions also work as quick writing prompts: choose, then give three reasons.
At youth group
Split into groups of four or five so that quieter people get a turn, and give each group three questions from one tag. Bring everyone back together to report the one that divided them most. Leaders should play in a group and not hover over one.
In the car with a parent
The car is the best place for the harder questions because nobody has to make eye contact. Ask one, answer it yourself, and leave the silences alone. Do not follow an answer with advice, and do not bring it up again at dinner as evidence.
Middle school, high school and rounds that go wrong
Middle school
Twelve to fourteen-year-olds like the Funny and School groups best and will act out anything. Stay near the top of each tag, where the choices are concrete. Keep the crush question, and the ones about switching schools or a missed party, for a group you know well.
High school
Older teens get bored when the stakes are low. Move quickly through the first few cards of a tag and spend the time on Fame and money, Hard choices and The future, where they have real decisions coming and real opinions about them.
Making a question harder
A lopsided vote means the question is too easy for this group. Change the terms until it splits: make the week a year, double the money, add an audience, close the loophole somebody found. Asking the group to repair the question is often more fun than the question was, and it is the quickest way to turn any card on the list into a hard one.
When it turns into teasing
A would you rather answer can become a nickname by Monday. The moment an answer is turned against the person who gave it, stop, say that answers stay in the room, and move to a new tag. If one person keeps being the target, end the game and start something else.
When an answer gets real
Sometimes a card about switching schools or quitting a team lands on something true. Thank the person, do not ask for more in front of everyone, and play a light card next. If it seemed to matter, check in later and privately.