Would You Rather Generator
“Would you rather wear a cape to every formal event or a bow tie to every casual one?”
Why ask it
A low-stakes opener that sorts the room into people who enjoy being looked at and people who would simply stop attending formal events.
Some of what is in the deck
Prefer to read than to shuffle? These are the opening cards of each deck, each with its note and the set it came from.
Everyone
Would you rather wear a cape to every formal event or a bow tie to every casual one?
Why ask it
A low-stakes opener that sorts the room into people who enjoy being looked at and people who would simply stop attending formal events.
Would you rather share every plate you order or never be allowed a bite of anyone else's?
Why ask it
There is a type of person who does not share food, and they know who they are. Ask this before ordering, not after, and plan accordingly.
Would you rather be able to instantly dry anything wet or instantly chill anything warm?
Why ask it
Tiny powers get better answers than grand ones because people picture using them today. Rainy commutes and warm soda come up within seconds.
Would you rather have unlimited free groceries and cook everything yourself or unlimited free restaurant meals and never choose the restaurant?
Why ask it
Free food with a catch on each side: labor or loss of control. Ask who they imagine choosing the restaurants, because people assume the worst.
Would you rather be able to mute any one person at a time or turn up the volume on any whisper?
Why ask it
One power is about peace and the other is about curiosity. Be ready for someone to name, a little too quickly, who they would mute.
Would you rather never be able to apologize or never be able to receive an apology?
Why ask it
People answer quickly and then reverse themselves once they think of a specific person. Let the silence run, because it is doing the work.
Would you rather go back to age ten knowing what you know now or jump ahead ten years with a guarantee that things turned out fine?
Why ask it
One option is a second chance and the other is relief from uncertainty. Whichever they choose, you find out which of those they are hungrier for.
Would you rather do work that matters and goes unnoticed or work that gets noticed and matters little?
Why ask it
Almost everyone claims the first. The honest conversation starts when you ask how long they could keep it up without a single thank you.
Would you rather get a standing ovation every time you parallel park or a slow clap every time you trip?
Why ask it
One option rewards you and the other mocks you, yet plenty of people take the slow clap because at least it is honest. Ask who is doing the clapping.
Would you rather be a minor character in a great story or the main character in an ordinary one?
Why ask it
Measures how much someone needs to be at the center. The follow-up that works: which great story, and which minor character?
Would you rather take the stairs every time or get the middle seat every time?
Why ask it
A small daily effort against a small occasional misery. Frequent flyers answer before you finish the sentence, and tall ones answer louder.
Would you rather take all your vacation in one long stretch each year or only ever one day at a time?
Why ask it
Splits people who need to get properly away from people who need a regular breather. Ask what the long stretch would be for, since it is often a trip they keep putting off.
Funny
Would you rather open a gift you clearly dislike in front of the giver or give a gift and watch them realize they already own it?
Why ask it
Tests acting ability against taste. Make them show the face they would pull, and let the group judge whether the giver would be fooled.
Would you rather hold a slug in each hand for an hour or wear a hat full of cold spaghetti for a day?
Why ask it
Slime you can see against slime you can only feel. Gardeners shrug at the slugs, which annoys everyone else in a satisfying way.
Would you rather have a tail that wags when you are happy or ears that droop when you are sad?
Why ask it
Either way your feelings are now public. Dog owners go for the tail, and someone always wants to know how it would work with chairs.
For kids
Would you rather be the zookeeper who brushes the hippo's teeth or the one who clips the sloth's toenails?
Why ask it
Two odd jobs, one quick and alarming, one slow and fiddly. Patient kids take the sloth. Ask what they would say to the animal to keep it calm.
Would you rather have a substitute teacher who is a magician or one who is an astronaut?
Why ask it
Tricks or true stories from space. Ask what the first lesson would be, and whether any actual math would get done that day.
Would you rather be small enough to ride a paper airplane or tall enough to rescue kites from any tree?
Why ask it
A fresher take on big versus small, because each size comes with a job. Ask what else they would do with a day at that height.
For couples
Would you rather I texted you all day about nothing or called once at lunch with my full attention?
Why ask it
Ask it before assuming your own preference is shared. Some people feel loved by a stream of small messages and others feel interrupted by it.
Would you rather know exactly where we will be in ten years or be completely surprised by it?
Why ask it
Planners and improvisers show themselves here. Whichever your partner is, the future will need a bit of the other, and that may be your job.
Would you rather recreate our first kiss or our first real conversation?
Why ask it
Asks which moment they count as the true beginning. You may find you each date the start of things from a different night.
For teens
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 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 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.
For adults
Would you rather have more hours in the day or more energy for the hours you already have?
Why ask it
Busy adults say 'hours' by reflex and switch to energy once they picture their evenings. What is the first thing they would spend it on?
Would you rather find fifty dollars in an old coat every month or get one surprise check for five hundred dollars once a year?
Why ask it
The coat pays more over twelve months, and plenty of people still take the check because a windfall feels like an event. Let someone do the arithmetic out loud.
Would you rather bring a homemade dish to every gathering you attend or be the one who works out how to split every bill?
Why ask it
Cooks go one way and spreadsheet people the other. Those who choose the bill have often been burned by a friend who 'only had a salad', so ask.
For work
Would you rather have your own desk to decorate or choose a different desk anywhere in the building each morning?
Why ask it
On a hot-desking team, ask which spot people hurry to claim. On a team with fixed desks, ask what one thing on the desk they would miss, and expect plants, photos and one very specific mug.
Would you rather have every meeting start exactly on time or end ten minutes early?
Why ask it
Asked at the top of a meeting, it is a gentle joke about the meeting itself. If the room votes heavily one way, you have just been told something useful for free.
Would you rather sit at the desk nearest the kitchen or the desk nearest the window?
Why ask it
The kitchen desk gets every passing conversation and the window desk gets daylight and peace. In an office with assigned seats, whoever already sits in one of these can report whether it lived up to the idea.
How to play would you rather
One person reads the card aloud. Everyone picks one of the two options, out loud or by a show of hands, and nobody may answer "neither" or "both". Then the reader asks at least one person why. The choosing takes five seconds. The reasons are the game.
Pass the phone to the left and deal again. There is no score and no winner, so stop while people are still arguing about the last card.
The rules worth keeping
- You have to chooseBoth options are meant to be about equally good or equally bad. Refusing to pick is the only wrong answer.
- Take the question as writtenNo loopholes, no third option, no asking what happens afterwards. If the card says forever, it means forever.
- Anyone may be asked whyThe reader picks who explains, and picks someone different each round. That keeps the quiet players in it.
Three ways to change the game
- Guess the roomBefore anyone answers, the reader predicts which option most people will choose. Count the hands and see.
- Defend the other sideAfter you choose, argue for the option you turned down for thirty seconds.
- CornersIn a classroom or a big group, each side of the room is an option. People walk to their answer, then one person from each side says why.
Choosing a would you rather deck
- EveryoneThe general deck: everyday dilemmas, food, superpowers and a few hard ones. It is clean, so it works for a class, a team or a table with grandparents at it.
- FunnyWritten only to get a laugh, from silly through gross and awkward to absurd. Still clean. Use it to warm a group up.
- For kidsWritten for ages five to twelve, with a note for the grown-up who is reading aloud. Gross in places, never scary.
- For couplesFor two people who are together. Many of these cards say "we" and "I", so they only make sense when a partner is asking.
- For teensFor ages about twelve to eighteen: school, phones, friends, fame and the future. Sharper than the kids' deck, and still nothing a teacher or parent would mind reading out.
- For adultsDilemmas with adult life in them: money and work, in-laws, group chats and a few hard trade-offs. Clean, so it is safe at a dinner or a work social.
- For workAnswerable in ten seconds at the top of a meeting, with nothing about pay, bosses or anything that ranks colleagues.
The sets behind it
Nothing is written on the fly. Every card comes from one of these question sets, and each set has the whole list in an order that builds.