Hypothetical Questions
One made-up situation per card, no options to pick from, and as many answers as there are players.
- Time
- 10–30 min
- Players
- Two or more people
- Best for
- Road trips, meeting warm-ups and family dinners
- Deck
- 150 questions in 6 categories
How to use these hypothetical questions
- Pick a category from the menu under the card, or keep “All categories”.
- Read the top card aloud and let everyone answer it, going around the group.
- Swipe the card away, or tap “Next question”, for the next one. Questions do not repeat until you have seen the whole category.
- Tap the heart to save a question on this device, or tap “Make a 10-question list” for a list you can copy.
When to ask hypothetical questions
A what-if question asks for imagination, not facts about yourself, so it suits groups who do not know each other well and families who think they know everything already. Answers grow as people add to them, which makes one card last longer than you would expect.
A long drive
Time travel and history and Inventions and new worlds give the car something to build on for miles, and the driver can answer without looking away from the road.
The start of a team meeting
One card from If you could or What would you do warms up a room in two minutes. Tricky choices work well when the meeting is about how the team works together.
Family dinner
Lucky breaks gets every generation at the table planning what they would do with buried treasure or a surprise day off, and everyone at the table hears a different plan.
Ways to play with hypothetical questions
Around the circle, one follow-up
The reader shows the card, and everyone answers in turn around the circle, with the reader going last. Then each player may ask one person a single “and then what?” about their answer before the phone moves to the next reader.
Predict, then answer
With two people, the one holding the phone reads the card and guesses out loud what the other will say. The other gives a real answer, and you talk about how close the guess was before swapping roles.
Five-minute journal prompt
For a writing group or a quiet morning at home, read one card and give everyone five minutes to write or draw an answer. When time is up, each person shares a single sentence from what they made.
Tips for better answers
- Ask “and then what?” once per card. The second answer is often more surprising than the first.
- Tricky choices have no score to win. Hearing how each person would handle the extra change or the found wallet is the whole point.
- Read the card, then wait a few seconds before anyone speaks, so quieter players have time to picture the scene.
All 150 hypothetical questions by category
The complete list, grouped by category. The cards above draw from the same list, so you can read ahead here and play there.
If you could
Small wishes and odd new powers: what you would add, change or keep around you.
- If you could borrow one animal’s sense for a week, like an owl’s night vision, which would you pick?
- Which building you have ever visited would you most like to live inside?
- Suppose the smartest computer ever built would answer one question from you. What do you ask?
- You get one extra hour each day that nobody else knows about. How do you use it?
- Imagine you could stay any age you like for one week. Which age, and why?
- You get to design the flag for a brand-new town. What goes on it?
- Picture any view you want outside your bedroom window. What do you see?
- Your bed can carry you anywhere while you sleep. Where do you wake up tomorrow?
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- Say you could bring one object from a fairy tale into real life. Which would it be?
- Which boring errand would you turn into a game, and how would the game work?
- You can hand out one made-up award to someone in this room. What is it for?
- Which talent would you give everyone in your town for a day, and what happens next?
- Pretend you can change the color of the sky for one day. Which color do you pick?
- If you could make one holiday come twice a year, which would you double?
- Given a garden that grows anything except food, what would you plant in it?
- Swap chores with someone in this room for a day: whose would you take, and why?
- Imagine you could stay up all night somewhere amazing without getting tired. Where are you?
- You can learn the true story behind one object in your home. Which object do you pick?
- Your backyard turns into a new landscape every month. Which one do you want first?
- Which everyday sound would you remove from the world if you had the power?
- If you could make one small thing in your town free for everyone, what would it be?
- Imagine a shelf that fixes anything you put on it overnight. What goes on it first?
- What would you paint on a giant blank wall in your town, if it were all yours?
- Suppose your shadow could do one job for you each day. What job would you give it?
- Picture a pair of glasses that shows one hidden thing about the world. What do they show?
What would you do
An unexpected situation lands in your lap, so what is your next move?
- What would you do on a day when every screen in the world switched off until sunset?
- You open your front door and find a friendly penguin waiting on the step. What’s your plan?
- The power goes out for a whole evening, but everyone is safe and warm. How do you fill the time?
- You’re put in charge of your workplace for one day. What changes first?
- A bus driver lets you pick the route for one whole day. Where does everyone go?
- Stuck at a train station for six hours with only a notebook and a pencil, what would you do?
- Your town asks you to plan a brand-new festival from scratch. What happens at it?
- A museum lets you rearrange one room however you like. What does it look like when you’re done?
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- A neighbor hands you the keys to their bakery for one Saturday. How does the day go?
- Tomorrow you have to teach a class on something you know well. What’s the lesson?
- The whole park is yours alone from sunrise to sunset. How do you spend the day?
- What would you do if every clock stopped and nobody knew the time for a whole day?
- Someone gives you a huge empty field for one summer. What do you build or grow there?
- You’re asked to name a new street in your neighborhood. What do you call it?
- The library says you can borrow anything at all for a week, not just books. What do you borrow?
- A film crew wants to follow you for one ordinary day. What would you make sure they saw?
- With no screens allowed, how would you keep a group of five-year-olds busy for an hour?
- Every chair in your home disappears for a week. How do you manage meals and work?
- You have one day and a camera to show a visitor the best of your town. Where do you go?
- What would you do as the only person awake on a long overnight flight?
- Your family lets you plan a whole weekend, as long as it costs very little. What’s the plan?
- An expert in anything offers to teach you for one afternoon. Which subject do you pick?
- You’re snowed in at a cozy cabin with this group for three days. Who does what?
- Halfway through cooking dinner for guests, you find the main ingredient is missing. What do you make instead?
- A new person joins your team and knows nobody. What would you do on their first day?
Time travel and history
Castles, old markets, first inventions and your town a hundred years from now.
- If you could watch any ancient wonder being built, which one would you pick?
- Spending one day in a school from two hundred years ago, what would surprise you most?
- You can bring one modern object back to the year 1800. What do you take, and how do people react?
- Which invention would you most like to see on the very day it was first shown?
- Picture your town exactly one hundred years from now. What has changed most?
- You’re a guest in a castle in the Middle Ages for a week. How do you spend your days?
- What everyday thing from today will seem old-fashioned and funny in fifty years?
- Which dish from any time in history would you love to taste, cooked the way it was back then?
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- Suppose you sailed across an ocean on an old wooden ship. What would be the hardest part?
- You land in a busy market from a thousand years ago. What do you want to see or buy?
- Which everyday object, like the zipper or the pencil, would you love to have invented first?
- A time machine drops you in your town on the day it was founded. What do you look for?
- Imagine watching dinosaurs for one safe afternoon from a hidden glass hut. What would you hope to see?
- Which job from long ago, like lamplighter or town crier, would you try for a day?
- You can taste the very first version of any food. Which food do you choose?
- What would you tell someone from the year 1900 about an ordinary day now?
- What do you think this exact spot looked like ten thousand years ago?
- Imagine people in the future studying our time in history class. What should they know about it?
- Landing fifty years in the future for one afternoon, what would you check first?
- Which puzzle from history would you most like solved, like how a great stone circle was built?
- Picture being the very first person to ride a bicycle. What goes through your head?
- Which old way of doing things would you bring back today, like letters written by hand?
- Which time period’s clothes would you happily wear every single day?
- If you could watch the very first game of any sport, which sport would it be?
- Living three hundred years ago, what modern comfort would you miss most?
Lucky breaks
Buried treasure, a prize you did not expect, a surprise free day: how do you use it?
- You dig up a rusty metal box in the backyard. What do you hope is inside?
- A surprise extra day off lands on a Tuesday. How do you spend it?
- You win a ticket to anywhere in the world, leaving tomorrow morning. Where do you go?
- A bakery picks you to name and design its new cake. What is it called, and what’s in it?
- Tucked inside a library book, you find a hand-drawn treasure map. Who do you bring along to follow it?
- Your town gives you the keys to the aquarium for one night. How do you spend it?
- You win a year of free lessons in anything you like. What do you sign up for?
- The ice cream truck lets you invent a flavor to sell all summer. What is it?
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- Your boss announces a surprise three-day weekend. What’s the plan?
- In an old coat pocket you find a gift card you forgot about. What do you buy?
- A museum lets you take one object home for a week. Which one do you choose?
- Your drawing wins a contest and gets painted on the side of a city bus. What did you draw?
- Every traffic light turns green for you for a whole day. Where do you go?
- A famous chef offers to cook any meal you like for you and your friends. What do you ask for?
- A bottle washes up on the beach with a note inside. What do you hope it says?
- You’re picked as the very first visitor to a brand-new theme park. Which ride do you try first?
- A musician you love offers to write a song about anything you choose. What’s it about?
- Every chore is already done and the afternoon is completely free. What do you do?
- Behind an old wall in your neighborhood, you discover a hidden garden. What’s growing there?
- A ferry captain lets you make the announcement over the speaker. What do you say?
- At a yard sale you find old photos of your own street. What do you look for first?
- Your library card suddenly works at every library in the world. Which one do you visit first?
- You win a night in the most unusual place to sleep you can imagine. Where is it?
- You enter a baking contest as a joke and win first prize. What did you bake?
- A whole week of perfect weather arrives and your calendar is empty. What do you do each day?
Inventions and new worlds
Gadgets, sports, colors and planets nobody has made or found yet.
- Dream up a gadget that would make mornings easier. What does it do?
- You discover a new planet. What do you name it, and what’s the weather like?
- Invent a new sport for this group. What are the rules, and how do you score?
- Mix two real animals into a brand-new one. What can it do?
- What would a city at the bottom of the ocean need that ours doesn’t?
- You find a color nobody has ever seen before. What do you call it?
- Come up with a new holiday. When is it, and how do people celebrate?
- Design a school bus or train from scratch. What’s inside that isn’t there now?
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- Your shop sells things nobody has invented yet. What’s on the shelves?
- On a planet where everything weighs half as much, what would you try first?
- Create a board game about your hometown. What’s it called, and how do you win?
- What would a playground on the moon look like?
- Describe a machine that turns one thing into another. What goes in, and what comes out?
- Sailing past an island nobody has mapped, you go ashore. What lives there?
- Invent a musical instrument that doesn’t exist yet. How do you play it?
- Design a house that can move. How does it get from place to place?
- Picture breakfast on a space station a hundred years from now. What’s on the plate?
- Create a new kind of weather. What falls from the sky, and what do people wear?
- Imagine an app that helps people be a little kinder each day. What does it do?
- Add a new piece to a game of chess. How does it move?
- If the alphabet got one new letter, what would it look like and sound like?
- In a world where everything is made of paper, what would daily life be like?
- Which kitchen tool do you wish existed, and how would it work?
- Build a vehicle for exploring a jungle without bothering any animals. What does it look like?
- Make up a word for a feeling that doesn’t have a name yet. What does it mean?
Tricky choices
Everyday honesty puzzles, like extra change, a found wallet or a gift that does not fit.
- The cashier hands you ten dollars too much in change. What do you do?
- You find a wallet on a park bench with an ID card but no phone number. What’s your next step?
- A friend knits you a sweater that’s three sizes too big. What do you say?
- The person ahead of you drops a glove and walks off without noticing. What do you do?
- You knock over a neighbor’s flower pot by accident, and nobody saw. What happens next?
- A vending machine drops two snacks instead of one. What do you do with the extra?
- Your manager forgets a deadline that would give you an easy week, and only you noticed. What would you do?
- You open a birthday present and it’s something you already own. How do you handle it?
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- The restaurant forgets to charge you for dessert. What do you do?
- Your group gets praised for an idea that was really the quietest member’s. What would you do?
- A library book turns up under your bed, three years overdue. What’s your plan?
- Two friends invite you to different things on the same afternoon. How do you decide?
- You know the ending of the mystery your friend just started. What do you say when they ask?
- Counting the score at the end of a game, you notice a mistake in your favor. What do you do?
- A friend proudly shows you a drawing you don’t really like. What would you say?
- One slice of pizza is left and everyone is too polite to take it. What do you do?
- A text meant for someone else arrives, and it’s a surprise party plan. What would you do?
- Right before a big poster goes up, you spot a spelling mistake on it. What would you do?
- You spill juice on a book you borrowed from a friend. How do you make it right?
- Two friends ask you to judge who won their race, and it looked like a tie. What do you say?
- When, if ever, would you use a trick that makes your favorite video game easy to win?
- Your neighbor is away for a week and their package lands on your doorstep. What do you do?
- Someone asks you directly about a surprise gift you know they’re getting. What do you say?
- A friend tells a story you were both part of, and gets half the details wrong. What do you do?
- You find someone’s work notes blowing across a parking lot, with a name on them. What would you do?
Frequently asked questions
How many hypothetical questions are there?
There are 150 questions, 25 in each of six categories: if you could, what would you do, time travel and history, lucky breaks, inventions and new worlds, and tricky choices. The cards and the list on this page use the same set.
Is there a what-if game for couples?
Yes. Would you still love me if is a set of playful what-ifs written for two people in a relationship. The questions on this page are for any group, with nothing about romance in them.
Are these questions okay for work?
Yes. Every card is about wishes, places, history, inventions or small everyday choices, with nothing personal or political. One makes a quick meeting warm-up, and Tricky choices make a gentle start to a talk about honesty and fairness.
What should we play after hypothetical questions?
Try would you rather questions. A hypothetical question leaves the answer wide open, while would you rather gives two set options and asks you to pick one, so the rounds are quicker and the talk is about why.