Hardest Would You Rather Questions, Plus 70 Deep Ones: how it works
The hardest would you rather questions make both options cost you something, such as Never say thank you again or never say sorry again. This deck has 140 clean cards, 70 hardest and 70 deep. Tap a side to vote.
Tough questions in five topics
The Hardest chip holds 70 tough would you rather questions, 14 in each topic: Both options cost you, Both options tempt you, One rule for life, Give one up for good and Skills and talents. Across both sets, Hard marks the 95 cards written to be argued over. No card is marked Easy, and "both" and "neither" are not answers.
Deep thinking questions, each with a follow-up
The Deep chip holds 70 more on Time, Memory, Who you are, What matters most and A good life. Every card has a Then ask line, printed in the list under the deck and not on the card. After Keep your body with new memories or keep your memories in a new body, it asks: Which one is still you?
Tips
Let the smaller side explain first, then read the Then ask line from the list aloud.
For a second round, give each side one minute to argue, press Clear votes and vote again.
Start a quiet table on Medium, 45 cards with a quicker pick, then move to Hard.
Questions and answers
What is the hardest would you rather question?
There is no single one, because a card is only hard when your table splits. Our pick to start: Give up the thing you are best at or give up the thing you enjoy most. The vote count shows how close your room came.
What are some deep would you rather questions?
Three from the Deep set: Relive one day as often as you like or get one extra day at the end. Remember exactly what happened or remember exactly how it felt. Get everything you want or want everything you already have.
Are there philosophical would you rather questions here?
Yes, four cards borrow a thought experiment. Live a perfect life inside a dream or live a bumpy life that is real is Robert Nozick's experience machine (1974). The others use the ship of Theseus, John Rawls's veil of ignorance and Plato's ring of Gyges.
Are the hardest would you rather questions for adults only?
No. Every card is clean: nothing sexual, no drinking and no dares, so adults and teens can share the deck. The cards are about work, time and values, which younger children may shrug at. For them, open the kids deck.
Would you rather always know the right thing to say or always know the right thing to do?Then ask: When did you last have one without the other?
Would you rather always leave the party too early or always stay an hour too long?Then ask: Which one does a host forgive faster?
Would you rather answer everything in one second or answer everything after a full minute?Then ask: Are your fast answers or your slow answers more like you?
Would you rather arrive on time and unprepared or arrive late and fully ready?Then ask: Which one do the people waiting for you mind more?
Would you rather be given the perfect mentor or be given the perfect rival?Then ask: Who has pushed you further so far, a teacher or a competitor?
Would you rather be the best at a useless skill or be average at a useful one?Then ask: Which useless skill would you pick?
Would you rather build anything you can imagine or imagine what no one else can?Then ask: Which is rarer, the idea or the hands to make it?
Would you rather celebrate every small win out loud or celebrate only the big ones?Then ask: What small win from this week went by without a cheer?
Would you rather decide everything by gut or decide everything with a written list?Then ask: Which of your best decisions was made which way?
Would you rather decide today with half the facts or decide in a year with all the facts?Then ask: What does waiting cost that the facts cannot repay?
Would you rather dine with anyone from history or watch any one event from history?Then ask: Would you rather ask the questions or see it for yourself?
Would you rather do every job yourself or teach every job to someone new?Then ask: Is it faster alone or better together, and which do you pick when it counts?
Would you rather do work that is finished by dinner or do work that lasts a hundred years?Then ask: Which kind of tired feels better at the end of a day?
Would you rather earn everything the slow way or be handed everything on day one?Then ask: What would you lose by skipping the slow part?
Would you rather eat one perfect dinner every night or never eat the same dinner twice?Then ask: How many nights before the perfect dinner stops being perfect?
Would you rather fix anything that breaks or grow anything you plant?Then ask: Which one would the neighbors knock on your door for?
Would you rather fly anywhere free for life or eat at any restaurant free for life?Then ask: Which one would you still be using in year twenty?
Would you rather get an hour alone every morning or get an hour with friends every night?Then ask: Which hour do you get less of right now?
Would you rather get one huge standing ovation or get quiet respect your whole life?Then ask: Would the memory of one big night last you?
Would you rather give the perfect gift every time or give the perfect advice every time?Then ask: Which do the people you love need more from you?
Would you rather give up all maps or give up all calendars?Then ask: Would you rather be unsure where you are or unsure when you are?
Would you rather give up every hobby you do alone or give up every hobby you share?Then ask: Which hobby would you try to sneak across the line?
Would you rather give up every inside joke or give up every nickname?Then ask: Which one holds more of your history with people?
Would you rather give up every true story or give up every made-up story?Then ask: Which kind has taught you more?
Show all 140 questions (116 more)
Hardest, continued
Would you rather give up the thing you are best at or give up the thing you enjoy most?Then ask: Are those two the same thing for you?
Would you rather give up weekends for good or give up vacations for good?Then ask: Do you rest better in small doses or in one long stretch?
Would you rather give up your birthday for good or give up your favorite holiday for good?Then ask: Which day is more about you, and is that the point?
Would you rather give up your oldest keepsake or give up your newest favorite thing?Then ask: What makes a thing hard to replace, its age or its use?
Would you rather have a small birthday every month or have one giant birthday a decade?Then ask: Is it the party you want, or being remembered often?
Would you rather have endless patience or have endless energy?Then ask: Which one runs out first in your house?
Would you rather have great taste and no talent or have great talent and no taste?Then ask: Which one would frustrate you more by the end of a year?
Would you rather have perfect timing or have perfect recall?Then ask: Which one would have saved you last week?
Would you rather hear all bad news first or hear all good news last?Then ask: Would you rather be ready, or be happy a little longer?
Would you rather hear every mistake you make replayed or never learn what you got wrong?Then ask: How much feedback is too much?
Would you rather hear every song only once or hear the same hundred songs for life?Then ask: Is music better when it is new or when you know every note?
Would you rather host every family gathering from now on or never host anyone again?Then ask: What does a host get out of the night that a guest does not?
Would you rather inherit a cabin full of old journals or inherit a boat with a marked map?Then ask: Do you want a story to read or a story to be in?
Would you rather keep a diary that anyone can read or never write anything down again?Then ask: Would you write differently, or just write less?
Would you rather lead well and never enjoy it or want to lead and never get the chance?Then ask: Should the job go to the person who wants it or the person who is good at it?
Would you rather learn fast and hit a ceiling or learn slowly with no ceiling?Then ask: How patient are you with being bad at something?
Would you rather learn one truth about the universe or learn one truth about your future?Then ask: Which question would you spend it on?
Would you rather live in one room with a huge view or live in a big house with no windows?Then ask: How often do you look out of the window now?
Would you rather lose every argument for a year or stay silent for a whole month?Then ask: What would you need to say that you could not write down?
Would you rather love the job but not the team or love the team but not the job?Then ask: Which one would you still be glad about on a Sunday night?
Would you rather make every group decision for life or never make a group decision again?Then ask: Is choosing for the group a power or a chore?
Would you rather never ask another question or never answer another question?Then ask: Which do you learn more from, asking or answering?
Would you rather never compete at anything again or never be on a team again?Then ask: Which do you need more, someone to beat or someone to pass to?
Would you rather never cook for anyone again or never be cooked for again?Then ask: Is a meal more of a gift when you make it or when you get it?
Would you rather never make a good first impression or never get the last word?Then ask: Which matters more in a friendship, how it starts or how each talk ends?
Would you rather never make another new friend or start over with all new friends?Then ask: What do old friends know that new ones never could?
Would you rather never say thank you again or never say sorry again?Then ask: Which word do you owe more of right now?
Would you rather never win again but keep improving or keep winning but never improve?Then ask: What is the score for, if not to show that you got better?
Would you rather owe everyone you know a favor or never be allowed to ask for one?Then ask: Is it harder for you to ask for help or to pay it back?
Would you rather own a door that opens anywhere or own a window that shows any year?Then ask: Are you someone who wants to go, or someone who wants to watch?
Would you rather own a garden that grows anything or own a library that holds every book?Then ask: Which one would you end up sharing more?
Would you rather plan every day down to the minute or never plan anything again?Then ask: What is the best day you ever had that nobody planned?
Would you rather say the wrong thing on time or say the right thing a day late?Then ask: Which one have you done more often?
Would you rather sit at the head of every table or sit wherever a seat is left?Then ask: Do you like a room better when you run it or when you watch it?
Would you rather spot talent in anyone or have one great talent yourself?Then ask: Would you rather be the star or the one who found the star?
Would you rather start a conversation with anyone or end any conversation gracefully?Then ask: Which one would you use more at a party?
Would you rather stay calm in every crisis or think fastest in every crisis?Then ask: Which one does your family need from you?
Would you rather take a job that travels the world or take a job with every evening free?Then ask: What would you do with all those evenings?
Would you rather take a paid year off right now or retire five years sooner?Then ask: Is free time worth more when you are young or when you are old?
Would you rather take the blame for a friend or let a friend take the blame for you?Then ask: Does your answer change if the friend would never find out?
Would you rather talk only face to face for life or talk only in writing for life?Then ask: Which of your friendships would change the most?
Would you rather teach anyone anything or learn anything from anyone?Then ask: Who is the best teacher you ever had, and what made them good?
Would you rather understand every language or be understood in every language?Then ask: Would you rather take in the world or be heard by it?
Would you rather wake up at five every morning or stay up until two every night?Then ask: When does your best hour of the day happen?
Would you rather wake up rested after four hours or sleep ten hours and enjoy all ten?Then ask: Is sleep a chore or a treat for you?
Would you rather win a prize for work you dislike or make your best work and show no one?Then ask: Who is the work for in the end, you or the audience?
Deep 70
Would you rather act the same in every group or be a different you in every group?Then ask: Which group gets the most honest version of you now?
Would you rather back a friend who is in the wrong or back a rival who is in the right?Then ask: What does loyalty owe to the truth?
Would you rather be born a hundred years earlier or be born a hundred years later?Then ask: What would you miss most from right now?
Would you rather be content and achieve a little or be restless and achieve a lot?Then ask: Which one sounds like the people you admire?
Would you rather be disliked as your real self or be loved as someone you pretend to be?Then ask: How long could you keep up the act?
Would you rather be fair and seen as unfair or be unfair and seen as fair?Then ask: How long could you stay fair with no credit for it?
Would you rather be happy without knowing why or know exactly what would make you happy?Then ask: Is knowing the recipe the same as having the meal?
Would you rather be judged by your best day or be judged by your average day?Then ask: How far apart are those two days?
Would you rather be known for your kindest moment or be known for your bravest moment?Then ask: Which moment of yours would each one be?
Would you rather be proud of what you did or be proud of how you did it?Then ask: Can you think of a time you had one without the other?
Would you rather be proven right in public or make peace in private?Then ask: What is being right worth if nobody else hears it?
Would you rather be remembered for a thousand years or change the world and be forgotten?Then ask: Is the point the change or the name on it?
Would you rather be remembered just as you were or be remembered as better than you were?Then ask: Who gets to decide which version is true?
Would you rather be the lead in a quiet story or be a side character in a grand one?Then ask: Which one describes your life so far?
Would you rather be the oldest in every room or be the youngest in every room?Then ask: Do you like being looked to or looked after?
Would you rather be trusted by everyone you meet or be able to trust everyone you meet?Then ask: Which one would make your days easier?
Would you rather be twenty-five for twenty years or be sixty-five for twenty years?Then ask: Which age do you think is the best one to stay at?
Would you rather change your mind too easily or almost never change your mind?Then ask: When did you last change your mind about something big?
Would you rather finish every task in half the time or enjoy every task twice as much?Then ask: What is all the saved time for?
Would you rather forget a favorite film to see it new or keep knowing every line by heart?Then ask: Is the first time really better than the tenth?
Would you rather forget your most awkward moments or have everyone else forget them?Then ask: Whose memory of it bothers you more, yours or theirs?
Would you rather forgive someone who is not sorry or wait years for an apology?Then ask: Who is forgiveness for, them or you?
Would you rather get a practice run at every day or get one redo a year?Then ask: Would a practice run make the real day better or flatter?
Would you rather get back every hour spent waiting or get back every hour spent worrying?Then ask: Which pile of hours do you think is bigger?
Would you rather get everything you want or want everything you already have?Then ask: Which one is harder to pull off?
Would you rather get ten extra years of childhood or get ten extra years of retirement?Then ask: Which years were, or will be, the freest?
Would you rather give everyone a second chance or get a second chance from everyone?Then ask: Which one do you find harder today, giving one or asking for one?
Would you rather grow old where you grew up or grow old somewhere you have never been?Then ask: What would you want within walking distance?
Would you rather have the courage to act or have the wisdom to wait?Then ask: Which one have you needed more this year?
Would you rather hear a friend's first memory of you or hear their best memory of you?Then ask: Do you think the two would be the same?
Would you rather hear how the future describes today or tell the past what today is like?Then ask: What about right now do you think will look strange later?
Would you rather keep your body with new memories or keep your memories in a new body?Then ask: Which one is still you?
Would you rather know your purpose and find it hard or never know it and enjoy the road?Then ask: Does a life need a point to be a good one?
Would you rather laugh hard every single day or be deeply moved once a month?Then ask: Which one do you remember longer?
Would you rather learn the strength you never noticed or learn the flaw you never noticed?Then ask: Which one could you do more with?
Would you rather live a friend's life for a week or watch a friend live yours for a week?Then ask: What would they do differently by Tuesday?
Would you rather live a perfect life inside a dream or live a bumpy life that is real?Then ask: Does it matter that it is real if it feels the same?
Would you rather live a small life you chose or live a big life chosen for you?Then ask: How much is the choosing worth to you?
Would you rather live among people who challenge you or live among people who comfort you?Then ask: Which kind of friend do you have more of?
Would you rather live by one motto for life or pick a new motto every year?Then ask: What would this year's motto be?
Would you rather live your years in order or live your years in a shuffled order?Then ask: Which age would you hope comes up first?
Would you rather lose every photo you have ever taken or never take another photo?Then ask: Which photo would you miss first?
Would you rather love every Monday or love every Friday twice as much?Then ask: What would have to change for Monday to win?
Would you rather make good days last twice as long or make bad days pass twice as fast?Then ask: Do the bad days teach you anything you would lose?
Would you rather never feel nostalgia again or never feel anticipation again?Then ask: Where do you spend more time now, in memories or in plans?
Would you rather never forget a kindness or never forget a lesson?Then ask: Which one slips away from you faster now?
Would you rather peak at twenty and remember it or peak at seventy and wait for it?Then ask: Is it better to look back on your best or to look forward to it?
Would you rather pick a new name or pick a new hometown?Then ask: How much of you is in your name?
Would you rather plant a tree you will never sit under or sit under one planted for you?Then ask: What did someone leave behind that you use every day?
Would you rather read your life story by a best friend or read your life story by a rival?Then ask: Which book would be more accurate?
Would you rather recall every talk word for word or forget every argument by morning?Then ask: Would a perfect record end arguments or start more of them?
Would you rather recover one memory from age two or make this week impossible to forget?Then ask: What do you hope the age-two memory would be?
Would you rather relive one day as often as you like or get one extra day at the end?Then ask: Which day would you pick, and would it survive being replayed?
Would you rather remember every dream you ever have or never remember a dream again?Then ask: Do your dreams tell you anything, or are they just noise?
Would you rather remember everything you read or remember everything you hear?Then ask: Where does most of what you know come from, pages or people?
Would you rather remember exactly what happened or remember exactly how it felt?Then ask: Which one does your family argue about more?
Would you rather remember one year perfectly or remember every year a little better?Then ask: Which year would you choose?
Would you rather see a photo of you in thirty years or keep the future a total surprise?Then ask: What would you look for first in the photo?
Would you rather set the rules and draw your role or pick your role and draw the rules?Then ask: What is the first rule you would write if you could end up as anyone?
Would you rather show a friend one memory of yours or see one memory of theirs?Then ask: Which memory, and which friend?
Would you rather sign everything you ever make or sign nothing you ever make?Then ask: Would you work differently with your name on it?
Would you rather spend a day with you at age ten or spend a day with you at age eighty?Then ask: Who would learn more from the visit?
Would you rather spend a week with your exact copy or spend a week with your opposite?Then ask: Which of your habits would annoy you first?
Would you rather spend every Sunday at a full table or spend every Sunday completely free?Then ask: What does your ideal Sunday look like by noon?
Would you rather stay exactly who you are now or become someone you cannot predict?Then ask: What about you has changed the most in five years?
Would you rather tell a truth that helps no one or keep a secret that hurts no one?Then ask: Is honesty about the facts or about the people?
Would you rather treat everyone exactly the same or treat the people you love best?Then ask: Where does fairness end and loyalty begin?
Would you rather try everything and regret some or choose carefully and wonder what if?Then ask: Which do you think about more, things you did or things you did not do?
Would you rather understand yourself completely or be understood completely by one person?Then ask: Which one do you have more of today?
Would you rather win by bending a rule nobody checks or lose while playing perfectly fair?Then ask: Would the win still feel like yours?
How this list was compiled: Own work: 140 two-option questions written for this page on 2026-09-19, 70 in the Hardest set and 70 in the Deep set, with none taken from another site's list. A script compared every question and every option with all the other decks on this site on 2026-09-19 (57,407 cards in 334 files): no question or option is repeated, close matches were read by hand, and 41 drafts that came too near a card in another deck, mostly the main, teen and adult would you rather decks and the this-or-that decks, were replaced. Every card was read against the site's family-safe rule and run through a word blocklist on the same day, which came back clean: nothing sexual, no alcohol or drugs, no self-harm, no dares, no brand names, no real people, nothing illegal, nothing about the death of a loved one, illness or money trouble, and neither option is a put-down of any group of people. No card has a right answer and no card was polled: the vote count on the page is your own table's, kept on your phone. The "Then ask" line after each question is a follow-up in our own words. Levels are an editor's judgment: Medium cards usually settle inside a minute, Hard cards are the ones the editors expect a table to argue over, and no card here is marked Easy. Four cards borrow a question from a well-known thought experiment, each checked on Wikipedia on 2026-09-19: the dream life or the real one, from Robert Nozick's experience machine in Anarchy, State, and Utopia, 1974 (https://en.wikipedia.org/wiki/Experience_machine); the body or the memories, after the ship of Theseus, which asks whether a thing is the same once its parts are replaced and was recorded by Plutarch (https://en.wikipedia.org/wiki/Ship_of_Theseus); setting the rules before you draw your role, from John Rawls's veil of ignorance in A Theory of Justice, 1971 (https://en.wikipedia.org/wiki/Veil_of_ignorance); and being fair with no credit for it, from the ring of Gyges story in Book 2 of Plato's Republic, which asks whether a person would act justly if they could never be caught (https://en.wikipedia.org/wiki/Ring_of_Gyges). The rule quoted on the page, that answering "both" or "neither" is against the rules, was checked the same day against https://en.wikipedia.org/wiki/Would_you_rather, and the meaning of dilemma (a problem offering two possibilities, neither of which is plainly preferable) against https://en.wikipedia.org/wiki/Dilemma. Licence: own work