200 Would You Rather Questions That Are Actually Hard to Answer

Most Would You Rather lists fail for the same reason: one option is obviously better. “Would you rather be rich or poor” is not a question, it is a formality. The whole game lives in the moment where a group genuinely splits and two people who agree on everything else start arguing about teleportation.

So these are sorted by who is in the room, and written so both sides cost you something. Twenty of them will fill an evening — the list is long so you can pick the right twenty, not so you can read all two hundred.

How to actually run it

• Make everyone commit. “Neither” and “both” end the round. Someone has to pick, and then defend it.
• Ask why immediately. The answer is worthless; the reasoning is the game. “Why?” is the only follow-up you need.
• Move your body if the group is big. Left side of the room for option A, right for B. It is faster than going round twenty people and you see the split instantly.
• Drop a question that lands flat. If the room agrees within five seconds, move on. Do not try to rescue it.
• Stop while people still want more. Twenty questions and out beats grinding through a list until it dies.

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Genuinely hard ones

The trade-offs where a group will actually split.

• Always know when someone is lying to you, or never have anyone lie to you again?
• Have your memory of the last ten years, or the ability to remember everything from now on?
• Be able to change one decision from your past, or see one decision from your future?
• Live twenty years longer, or know exactly how long you have?
• Be respected by everyone and liked by nobody, or liked by everyone and respected by nobody?
• Never feel physical pain again, or never feel embarrassment again?
• Have unlimited money but only ten more years, or a normal income and a full life?
• Be able to speak every language, or talk to every animal?
• Always have to say what you are thinking, or never be able to speak again about anything that matters?
• Know how the world ends, or know how you die?
• Be famous for something you did not do, or anonymous for something great you did?
• Read every book ever written, or have every conversation you ever wanted with anyone alive?
• Lose the ability to lie, or lose the ability to keep a secret?
• Have one true friend for life, or fifty good friends who come and go?
• Be the best in the world at something nobody cares about, or mediocre at something everyone values?
• Live the same perfect day forever, or a normal life with all its bad days?
• Never be bored again, or never be tired again?
• Have your ideal job for half the money, or a job you dislike for triple?
• Always be five minutes late, or always thirty minutes early?
• Have people always underestimate you, or always overestimate you?

Funny ones

Lower stakes, faster laughs. Good for warming a room up.

• Fight one horse-sized duck or a hundred duck-sized horses?
• Have hiccups for a year or feel like you need to sneeze and never do?
• Have fingers as long as your legs, or legs as long as your fingers?
• Sound like a cartoon character forever, or have a laugh that sounds like a car alarm?
• Only ever be able to whisper, or only ever be able to shout?
• Have a permanent unibrow, or permanently uneven eyebrows?
• Sweat maple syrup, or cry glitter?
• Have to sit down every time you speak, or stand up every time you eat?
• Always have to enter rooms by rolling, or always leave by walking backwards?
• Have your search history read aloud at your birthday, or your texts read aloud at work?
• Be unable to use your thumbs, or unable to close your eyes?
• Have a personal theme song that plays whenever you walk in, or a laugh track after everything you say?
• Wear shoes two sizes too big or clothes one size too small, forever?
• Have to announce your age before speaking to anyone, or your salary?
• Only be able to eat food that is beige, or only food that is green?
• Have every photo of you be a bad one, or never appear in a photo again?
• Have a snooze button for life that skips ten minutes, or a rewind button that costs a day?
• Have everything you own be slightly sticky, or slightly damp?
• Be followed everywhere by a mediocre marching band, or narrated by a bored documentary voice?
• Have all your clothes be one colour, or all your food be one flavour?

For adults

Real trade-offs, the kind people have actually thought about.

• Retire at forty with a modest income, or at sixty-five with a large one?
• Work four days a week for less money, or five for more?
• Live somewhere you love and commute badly, or somewhere dull with a five-minute walk?
• Have a job you love with a manager you cannot stand, or the reverse?
• Never work again but never travel, or travel constantly for work?
• Own a home you cannot leave, or rent forever and go anywhere?
• Have complete financial security and no ambition, or constant ambition and no security?
• Be able to nap anywhere for twenty minutes, or need only four hours of sleep?
• Know exactly what your friends really think of you, or never wonder again?
• Have your twenties back with what you know now, or an extra twenty years at the end?
• Lose all your photos, or all your music and books?
• Never argue with anyone again, or always win every argument?
• Have a partner who is your best friend but not exciting, or exciting but not your best friend?
• Be able to eat anything with no health consequences, or never need to exercise?
• Live without the internet, or without leaving your city?
• Always be the smartest person in the room, or always the funniest?
• Have to redo one year of your life, or skip one year entirely?
• Know every truth about the world, or be happily wrong about most of it?
• Give up coffee forever, or give up your favourite meal forever?
• Have one perfect month a year and eleven mediocre ones, or twelve consistently fine ones?

For couples

Ask these with someone you actually like. The follow-up matters more than the answer.

• Would you rather we always tell each other everything, or keep a few things private?
• Live near your family or mine?
• Have a small wedding and a big holiday, or the reverse?
• Spend a weekend doing exactly what you want, or exactly what I want?
• Know how we met from my point of view, or how I felt six months in?
• Always go to bed at the same time, or wake up at the same time?
• Have a house with one perfect room, or a whole house that is fine?
• Take one long trip every three years, or a short one every few months?
• Argue immediately, or wait until you are calm?
• Be told when you are wrong straight away, or given time to notice yourself?
• Have a partner who plans everything, or one who never plans anything?
• Spend an evening with old friends of yours, or make new ones together?
• Know exactly what I want for my birthday, or be surprised by what you choose?
• Live in a city we both like a bit, or one you love and I tolerate?
• Have one shared hobby, or separate ones you each love?
• Get a note every morning, or a proper conversation every evening?
• Move somewhere new every three years, or stay put for thirty?
• Have children early and be tired, or later and be sure?
• Split every chore evenly, or each own the ones you mind least?
• Be remembered by each other as we were at the start, or as we are now?

For work and icebreakers

Nothing here requires anyone to disclose anything personal, which is the whole point.

• Work fully remote or fully in an office?
• Have three short meetings a day, or one long one a week?
• Be given a deadline that is too tight or a project with no deadline at all?
• Get detailed feedback that stings, or vague praise that helps nobody?
• Join a team of experts and be the weakest, or a beginner team and be the strongest?
• Have unlimited holiday you feel guilty taking, or twenty-five days you take fully?
• Present to a thousand strangers, or to your five closest colleagues?
• Always have to write the summary, or always have to read everyone else’s?
• Work on one project for two years, or six projects in one year?
• Have a brilliant manager and dull work, or dull management and brilliant work?
• Answer email once a day, or take calls whenever they come?
• Learn a completely new skill every year, or master one over ten?
• Sit next to the noisiest person in the office, or the coldest window?
• Never attend another meeting, or never send another message?
• Have your work be highly visible and heavily criticised, or invisible and safe?
• Start work at six and finish at two, or start at eleven and finish at seven?
• Get a bonus you cannot tell anyone about, or public recognition with no bonus?
• Be the person who spots problems, or the person who fixes them?
• Have a two-hour lunch and work later, or eat at your desk and leave early?
• Be trusted completely and left alone, or supported closely and checked often?

For big groups

Fast to answer, easy to split a room in half.

• Be able to fly slowly, or run extremely fast?
• Have unlimited free travel, or unlimited free food?
• Always know the time exactly, or always know which direction is north?
• Live in a treehouse or on a boat?
• Never wait in a queue again, or never sit in traffic again?
• Have every meal cooked for you, or your house cleaned forever?
• Be able to pause time for ten minutes a day, or rewind ten seconds once a week?
• Live in the mountains or by the sea?
• Have perfect pitch or perfect balance?
• Never lose anything again, or never forget a name?
• Be able to teleport only to places you have been, or fly anywhere slowly?
• Always have perfect weather, or never have to pack a bag?
• Have a personal chef or a personal driver?
• Be able to breathe underwater, or survive any temperature?
• Never be stuck in small talk again, or never be lost again?
• Have one extra hour every day, or one extra day every month?
• Always get the window seat, or never have a middle seat?
• Be able to speak to crowds without fear, or write anything effortlessly?
• Have a photographic memory for faces or for text?
• Never have a bad haircut, or never have a bad night’s sleep?

Food

Surprisingly divisive. Good filler between heavier rounds.

• Give up cheese or chocolate?
• Only eat at the best restaurant in your city, or cook every meal yourself perfectly?
• Have every meal be breakfast, or never eat breakfast again?
• Eat something delicious that looks awful, or something bland that looks incredible?
• Never eat your favourite food again, or eat only that for a month?
• Have unlimited takeaway or a perfect home-cooked meal every Sunday?
• Only ever drink coffee or only ever drink tea?
• Eat food that is always slightly too hot, or always slightly too cold?
• Give up all sweet food or all salty food?
• Have a fridge that refills itself with the same ten things, or a wildcard delivery every day?
• Eat alone in silence at the best table, or crowded and loud with friends?
• Never season anything again, or season everything too much?
• Have dessert before every meal, or never have dessert again?
• Only eat food you can hold, or only food you need cutlery for?
• Try every cuisine once, or master eating well in one?

Travel and places

Reliably splits a room, and nobody has to reveal anything about themselves.

• See ten countries badly, or one country properly?
• Travel alone or always with the same person?
• Have a month off every year to travel, or a year off once a decade?
• Only visit cities, or only visit places with no cities?
• Always fly and never see the journey, or only travel overland?
• Stay in the best hotel in a dull town, or a bad hostel somewhere extraordinary?
• Have every trip planned to the hour, or nothing booked but the flight?
• Live abroad for five years, or take twenty short holidays?
• Never see a famous landmark again, or never eat local food again?
• Go somewhere no one you know has been, or somewhere everyone you know loves?
• Travel to the past for a week, or the future for a day?
• Speak the language badly everywhere, or perfectly in one country only?
• Lose your luggage every trip, or always have a middle seat?
• Live somewhere with four dramatic seasons, or endless mild weather?
• Have a home you return to, or no fixed address at all?
• Revisit your favourite place every year, or always go somewhere new?
• Take a two-day train journey, or a two-hour flight and lose the view?
• Have someone else pay but choose the destination, or pay yourself and choose freely?

Technology and the future

Good for a mixed group and surprisingly heated.

• Give up your phone for a month, or the internet for a week?
• Have every message you send be public, or never be able to delete anything?
• Know everything an algorithm knows about you, or never be recommended anything again?
• Have a self-driving car you never control, or drive everywhere yourself forever?
• Live without maps, or without a camera?
• Have perfect voice control of everything, or never speak to a machine again?
• Back up your memories to a device, or keep them fallible and private?
• Have a robot that does your least favourite task, or two extra hours of sleep?
• Know when a photo has been edited, or never see an edited one again?
• Have every device last ten years, or always have the newest one free?
• Read only physical books, or only screens?
• Have all your passwords replaced by your face, or memorise a hundred of them?
• Never receive another notification, or never send another message?
• Live in a house that anticipates what you want, or one that does nothing automatically?
• Have your job automated but be paid the same, or keep the work and the wage?
• Video call everyone always, or only ever send text?
• Know exactly how much time you spend on your phone, or never find out?
• Have one device that does everything badly, or five that each do one thing perfectly?

Deeper ones

For a small group, late, when the room has gone quiet.

• Be remembered inaccurately, or forgotten completely?
• Know what everyone thinks of you, or what you actually think of yourself?
• Have a life that is meaningful and hard, or pleasant and forgettable?
• Understand why bad things happened to you, or stop needing to?
• Be the person you are, or the person you meant to become?
• Have one conversation with someone you lost, or a letter you can read forever?
• Know that your work outlives you, or that your friendships did?
• Be able to forgive instantly, or never need to?
• Have your children be happy or be extraordinary?
• Know the truth about something that would hurt, or live with the version you have?
• Change one thing about the world, or one thing about yourself?
• Be certain about something wrong, or uncertain about something right?
• Have more time or more courage?
• Be understood by one person completely, or admired by thousands?
• Feel everything intensely, or feel steady all the time?

Family and mixed ages

Safe for a table with grandparents and eight-year-olds at it.

• Have a pet dinosaur or a pet dragon?
• Be able to talk to animals, or have animals understand you?
• Live in a world with no rain, or no snow?
• Be the tallest person you know, or the fastest?
• Have a treehouse or a secret room?
• Only travel by boat or only by train?
• Be able to draw anything perfectly, or sing anything perfectly?
• Have summer all year, or winter all year?
• Be invisible for a day, or able to fly for an hour?
• Have a robot that does your chores, or one that does your homework?
• Meet someone from a hundred years ago, or a hundred years from now?
• Always have to hop, or always have to spin before sitting down?
• Have a garden full of anything you plant, or a bookshelf that refills itself?
• Be able to make anyone laugh, or make anyone feel calm?
• Have a birthday every month, or one enormous birthday every five years?

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When the questions run out

Would You Rather has one structural limit: somebody has to be reading prompts. It works brilliantly for twenty minutes and then the reader gets bored of being the reader, or the list runs dry and people drift back to their phones.

That is the gap Hidden Agenda fills. It is a party game where the prompts are private — each player gets three secret missions to pull off during the conversation, like steering the topic somewhere specific or getting someone to agree with a deliberately vague statement, and scores the ones nobody catches. Nobody reads anything aloud, nobody waits their turn, and the game runs underneath the evening instead of pausing it.

Different game, same instinct: give people a reason to say something more interesting than what they did at work today. Free on the App Store.

If you want more question-based games, our guide to conversation games covers the decks and formats worth owning, and social deduction games covers the ones where somebody is lying to you.