Trick Questions to Ask
For anyone who wants to trip up friends, family, a class or a group chat with questions that have a catch in them. The 60 trick questions are sorted into six groups in the order a round usually goes: Warm ups, Out loud, Wordplay, Numbers, Logic and Hardest. Every note gives the answer, explains the trap and says how to ask the question without giving it away.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Warm ups
How many months of the year have 28 days?
Why ask it
All twelve, since every month gets at least as far as the 28th. People say one because the number points straight at February. If they get it, follow up with how many months have 30 days, which is eleven.
Which weighs more: a ton of bricks or a ton of feathers?
Why ask it
Neither, because a ton is a ton whatever it is made of. Bricks is the answer you get from anyone picturing one brick next to one feather. When somebody gets it right, ask which pile would be bigger, since that is the picture that fooled everyone else.
Mary's father has five daughters: Nana, Nene, Nini and Nono. What is the fifth daughter's name?
Why ask it
Mary. The four rhyming names set up a pattern, so most people say Nunu before noticing that the answer was in the first word of the question. Read the names slowly and with relish, because the rhythm is what catches people.
An electric train is heading north at full speed while the wind blows from the west. Which way does the smoke drift?
Why ask it
There is no smoke, because the train is electric. Anyone who starts working out wind direction with their hands has already lost. Say 'electric' in an ordinary voice and do not linger on it.
What two things can you never eat for breakfast?
Why ask it
Lunch and dinner. Expect guesses about soup or pizza first, and somebody claiming they have eaten last night's dinner for breakfast, which is a fair point and worth conceding with a smile. Young children can usually get there with one hint.
A plane comes down right on the border between the United States and Canada. Where do they bury the survivors?
Why ask it
Nowhere, because survivors are alive. The border is the decoy: people start weighing up which country has the better claim, and a few suggest splitting the difference. Say 'survivors' no louder than the rest of the sentence, and swap in two countries your group knows.
If you throw a blue stone into the Red Sea, what does it become?
Why ask it
Wet. The two colors send people looking for purple, or for something clever about the name of the sea. The answer is so plain that the groan comes from the whole room at once, which makes it a good one for a big group.
A rooster lays an egg right on the ridge of a barn roof. Which side does the egg roll down?
Why ask it
Neither side, because roosters do not lay eggs. Listeners ask how steep the roof is or which way the wind is blowing, and every sensible question takes them further from the bird. Anyone who has kept chickens gets it right away, so it is best on a group that buys its eggs in a carton.
On the ark, how many of each animal did Moses bring along?
Why ask it
None, because the ark was Noah's. Two is what you will hear, said with total confidence, because the question sounds like one everybody already knows. Ask it early: once a group has been caught by a swapped name, they check every name for the rest of the game.
How many sides does a circle have?
Why ask it
Two, the inside and the outside. Those who say none or one are thinking of geometry class, and those who say infinite are thinking of it too hard. This is a joke answer more than a fact, so give it up cheerfully if a math teacher objects.
What can you hold in your left hand but never in your right?
Why ask it
Your right hand, or your right wrist or elbow. People search the room for an object when the answer is attached to them. It works best face to face, where you can watch someone quietly try it under the table.
In a one-story house, the walls are pink, the carpet is pink, the couch is pink and even the cat is pink. What color are the stairs?
Why ask it
There are no stairs in a one-story house. The list of pink things is there to make 'pink' feel inevitable, so add a few of your own and take your time over them. If someone argues for basement stairs, give them the point and move on.
How can a person go eight days without sleep?
Why ask it
By sleeping at night. It sounds like an endurance record, so the guesses run to coffee and willpower. Someone who gets it at once has probably heard it before, so ask them to sit on the answers for the next few.
Out loud
Say 'toast' five times fast. What do you put in a toaster?
Why ask it
Bread. Toast is what comes out. The chanting loads the word so heavily that it is said again before the person has thought at all. Ask the second part the instant they finish, since a pause of even two seconds lets the right answer through.
Spell 'shop' out loud. What do you do when you come to a green light?
Why ask it
Go. Most people say stop, because the spelling leaves the rhyme sitting in their mouth. Drivers fall for it as readily as children do, and they are far more embarrassed about it.
Say 'silk' ten times as fast as you can. What do cows drink?
Why ask it
Water. Milk is what cows make, and the chant has the word ready before anyone has pictured an animal at a trough. Keep it well apart from the toast question, because one chant in a round is a surprise and two is a pattern.
What does Y-E-S spell? And what does E-Y-E-S spell?
Why ask it
Eyes. After an easy 'yes', nearly everyone hears the second one as 'e-yes' and looks puzzled that it is not a word. Spell the letters at an even pace, and never type it, because on a screen the word is simply sitting there.
How do you pronounce M-A-C-D-O-N-A-L-D, then M-A-C-B-E-T-H, then M-A-C-H-I-N-E-S?
Why ask it
The third word is machines. Two Scottish names in a row set the pattern, and people say 'Mac-Hines' with a straight face. Have them say it twice more before you spell it again slowly, because the second and third attempts are the funny ones.
You are driving a bus. Six people get on at the first stop, two get off and five get on at the second, and three get off at the third. What color are the driver's eyes?
Why ask it
Whatever color the listener's eyes are, since the opening sentence made them the driver. Everyone is busy keeping count of passengers, and some will proudly announce six. If they ask to hear it again, repeat only the first sentence and watch it land.
Add this up in your head as I say it: 1,000 plus 40, plus 1,000, plus 30, plus 1,000, plus 20, plus 1,000, plus 10. What is the total?
Why ask it
The total is 4,100. Most people say 5,000, because the last step takes the running total from 4,090 past a hundred and the mind rolls over the thousands instead. Pause after each number so they can keep up, and hand doubters a pen afterward.
Wordplay
Which word in the dictionary is spelled incorrectly?
Why ask it
The word 'incorrectly'. People assume you mean a famous misprint and start guessing at hard words. It reads as well in a message as it sounds out loud, so it is a safe pick for a group chat.
What five-letter word gets shorter when you add two letters to it?
Why ask it
Short, which becomes 'shorter' when you add 'er'. The trap is hearing 'shorter' as a description when it is the answer itself. If they are stuck, tell them the answer is in the question, and that hint is usually enough.
What comes once in a minute, twice in a moment and never in a thousand years?
Why ask it
The letter M. Guesses tend to be about time: a heartbeat, a blink, a second chance. Written down it is slightly easier, because the reader can look at the words themselves, so say it aloud if you want it to last.
What is at the end of every rainbow?
Why ask it
The letter W. Half the room says a pot of gold and the other half says a rainbow has no end, and both are answering a question about rainbows when you asked one about a word. Do not ask it straight after another letter trick, because the second one is spotted at once.
Which is correct to say: 'the yolk of an egg is white' or 'the yolk of an egg are white'?
Why ask it
Neither, because yolks are yellow. The question dresses itself up as a grammar test, and people pick 'is' with great confidence. Sticklers fall hardest, so aim it at the person who corrects everyone else's messages.
What has four letters, sometimes has nine and never has five.
Why ask it
It is a statement, not a question: the word 'what' has four letters, 'sometimes' has nine and 'never' has five. Spoken, your voice has to stay flat at the end, which is hard to do. It is at its best typed into a chat with a period, where people will guess for ten minutes before someone notices the punctuation.
A cowboy rides into town on Friday, stays three nights and rides out on Friday. How is that possible?
Why ask it
His horse is named Friday. Listeners try to make the calendar work, with time zones or a very long week. If someone asks 'which Friday?', they are close, so give them a moment before you answer.
A butcher stands six feet tall and wears size 12 shoes. What does he weigh?
Why ask it
Meat. The height and shoe size are there to make it sound like an estimate, and you will get numbers in pounds. Drop it in between two harder questions when the group needs an easy laugh.
How many seconds are there in a year?
Why ask it
Twelve: January 2nd, February 2nd and so on. Somebody will start multiplying 60 by 60 by 24, and it is kinder to stop them before they reach for a calculator. A sharp player may claim 24 by counting each month's 22nd as well, and they deserve the point.
Do they have a Fourth of July in England?
Why ask it
Yes: every country has a July 4th, between the 3rd and the 5th. People answer no because they hear the holiday and not the date, so it lands best with Americans and falls flat with anyone to whom 'Fourth of July' is only a date.
How far can a dog run into the woods?
Why ask it
Halfway, because after that it is running out of the woods. You will be asked how big the woods are and how fit the dog is. This is one to leave with the group for a minute, since someone usually reasons their way to it out loud.
How do you drop a raw egg onto a concrete floor without cracking it?
Why ask it
Any way you like, because concrete floors are very hard to crack. The 'it' is the trick: listeners assume it means the egg and start designing parachutes. Hold the answer back for a while, since the plans get more elaborate the longer you wait.
What question can you never honestly answer yes to?
Why ask it
'Are you asleep?' is the usual answer, and 'Are you dead?' works too. There is no misdirection here, only a hunt, so it gives the group a breather after a run of being fooled. Accept anything that fits, because people come up with good ones of their own.
Numbers
How many times can you subtract 5 from 25?
Why ask it
Once. After that you are subtracting 5 from 20. Five is what you will be told, and it is a perfectly good answer to a different question. Children who have just learned division enjoy catching adults with this one.
What do you get if you divide 30 by a half and add 10?
Why ask it
Seventy. Dividing by a half doubles the number, so 30 becomes 60 before the 10 goes on, while most people halve it and say 25. A doubter can usually be won over by asking how many half pizzas there are in 30 pizzas.
Fifteen kids are at a birthday party, and all but eight go home at four o'clock. How many are still at the party?
Why ask it
Eight. 'All but eight' already names the ones who stay, yet two numbers sitting side by side make people subtract and say seven. Ask for the answer quickly, because the phrase is easy to hear correctly given a second to think.
A farmer has four haystacks in one field and five in another. How many haystacks does he have when he puts them all together?
Why ask it
One big one. Nine comes out before the listener has pictured what putting haystacks together looks like. It pairs well with a real sum asked just before it, so that the group is already in adding mode.
Mr. Lopez has four daughters, and each daughter has one brother. How many children does he have?
Why ask it
Five, because the four girls share the same brother. Eight is the common wrong answer, from giving each daughter a brother of her own. If someone says five right away, have them explain it to the others, which is harder than it looks.
If eight people took ten hours to build a wall, how long would four people take to build it?
Why ask it
No time at all, because the wall is already built. People double the hours and say twenty, which would be right for a second wall. Stress nothing when you read it, since leaning on the last word gives the game away.
Which month do people sleep the least?
Why ask it
February, because it has the fewest nights. Guesses go to summer for the light evenings or December for the parties, and people defend them with real feeling. The plain answer is funnier after a serious debate, so do not cut the arguing short.
Ten candles are burning and a draft blows out three. How many candles are left in the morning?
Why ask it
Three, the ones that went out. The other seven kept burning until there was nothing left of them. Seven is what nearly everyone says, and the right answer usually gets a pause and then a slow nod, which makes it a satisfying one to explain.
You have two coins that add up to 30 cents, and one of them is not a nickel. What are they?
Why ask it
A quarter and a nickel: one of them is not a nickel, and that one is the quarter. People hear the phrase as ruling nickels out altogether and declare it impossible. It needs American coins, so rebuild it with your own if you are playing elsewhere.
How many bricks does it take to finish a brick house?
Why ask it
One, the last one. The word 'finish' does the work, and people who hear 'build' start estimating in thousands. Ask it of whoever is most practical-minded in the group, who will want to know the size of the house first.
How many times does the letter F appear in this sentence: 'The first of the five friends left half of the pie for the rest of us'?
Why ask it
Nine. Six is the usual count, because the eye skips the word 'of', where the F sounds like a V. This is one to show and not say: put it on a screen or a card, give people ten seconds and collect their numbers before anyone recounts.
Logic
You walk into a dark cabin with one match. Inside there is a candle, an oil lamp and a wood stove. What do you light first?
Why ask it
The match. Listeners weigh up which item gives the most light or heat, and some make a very sensible case for the candle. A thoughtful wrong answer is the best outcome here, because the person has reasoned carefully past the only thing in their hand.
Two fathers and two sons go fishing. Each catches one fish, and they bring home three fish in total. How?
Why ask it
There are only three people: a grandfather, his son and his grandson. The man in the middle is both a father and a son. People assume one fish got away or was eaten, so tell them nobody lost a fish and suggest they count the people instead.
A doctor and a boy are waiting for a bus. The boy is the doctor's son, but the doctor is not the boy's father. Who is the doctor?
Why ask it
His mother. Some people reach for stepfathers and adoptions before the simple answer. It catches fewer people than it once did, and when a group gets it instantly that is a good result, so say so and move on.
A truck driver goes the wrong way down a one-way street, passes a police officer and is not stopped. Why?
Why ask it
He is walking. Calling him a truck driver puts a truck in the listener's mind without the question ever mentioning one. Guesses include an emergency or an officer looking the other way, and you can tighten it by replying that the officer saw him clearly.
A man walks for an hour in pouring rain with no hat, hood or umbrella, and not a hair on his head gets wet. How?
Why ask it
He is bald. People propose awnings, tunnels and very large trees. This one is nearly always solved if you give it time, so do not rush in with the answer, and skip it if anyone in the room is touchy about a hairline.
Can a man marry his widow's sister?
Why ask it
No, because a man with a widow is dead. People treat it as a question about law or custom and start debating whether it is allowed where they live. Say it at normal speed, and watch whoever asks you to repeat it, because they are usually about to get it.
You overtake the last runner in a race. What place are you in now?
Why ask it
It cannot happen. If that runner is last, there was nobody behind them to do the overtaking. Second to last is the usual answer. A track runner may point out that you could be lapping them, which is correct and deserves the win.
Hardest
A man points at a portrait and says: 'Brothers and sisters I have none, but that man's father is my father's son.' Who is in the portrait?
Why ask it
His son. 'My father's son' can only be the speaker himself, since he has no brothers, so the line comes down to 'that man's father is me'. Almost everyone says he is looking at himself. Have a pen handy, because it is far easier to see written down than to hold in your head.
A snail is at the bottom of a 10-foot well. Each day it climbs 3 feet and each night it slips back 2. On which day does it get out?
Why ask it
Day eight. It gains a foot a day, so it starts the eighth day at seven feet and climbs the last three without slipping back. Ten is the tempting answer. Draw the well if you are doing it with children, and have them move a finger up it one day at a time.
A patch of lily pads doubles in size every day and covers the whole pond on day 30. On which day was the pond half covered?
Why ask it
Day 29, since one more doubling fills the pond. Fifteen comes out almost by reflex, because halving the days feels like the obvious move. People who get this right tend to go quiet for a second first, and that pause is the thing to praise.
If a hen and a half lays an egg and a half in a day and a half, how many eggs do six hens lay in six days?
Why ask it
Twenty-four. One hen lays one egg every day and a half, which is four eggs in six days, times six hens. The halves are there to make people give up and say six. Hand out paper, allow a couple of minutes, and take it one step at a time when you explain.
How many times does the digit 9 appear when you write out every number from 1 to 100?
Why ask it
Twenty. There are ten in the units place and ten in the tens place, and 99 has one of each. Ten and eleven are the common answers, from forgetting the nineties. It is a real counting problem with no wordplay, so it suits a class, and a doubter can simply list them.
How many times do the hands of a clock overlap in 24 hours?
Why ask it
Twenty-two. The minute hand passes the hour hand eleven times every twelve hours, not twelve, because the overlap you would expect just after eleven does not arrive until twelve. Twenty-four is the quick answer, and anyone with an analog watch can check by turning the crown.
What letter comes next: O, T, T, F, F, S, S?
Why ask it
E, for eight. The letters are the initials of one, two, three and so on. People look for a pattern in the alphabet or on a keyboard. It can take a long while, so offer one hint after a minute: try counting out loud.
A man pushes his car up to a hotel and realizes he is bankrupt. What is going on?
Why ask it
He is playing Monopoly, and his token is the car. Run it as a yes-or-no puzzle, where the group may ask you anything that can be answered with one of those two words. When nobody is getting anywhere, the best hint is that the car is very small.
A girl has as many brothers as sisters, but each of her brothers has only half as many brothers as sisters. How many children are in the family?
Why ask it
Seven: four girls and three boys, so each girl has three sisters and three brothers, and each boy has two brothers and four sisters. The trap is forgetting that nobody counts themselves. Keep it for a group that asked for a hard one, since it takes a few minutes and a pencil.
How to ask trick questions so they land
Practical guidance for the conversation itself
Before you ask
Get caught by it yourself first
Read the question, answer it honestly, then read the note. If it caught you, you know exactly where the trap sits and how it feels to step in it. If you cannot explain why the answer is right in one sentence, pick a different question, because a trick you have to defend at length stops being fun.
Say it once, at normal speed
The catch is nearly always one ordinary word: electric, survivors, widow, finish. Slow down or lean on that word and you have given it away. Read the question the way you would ask the time, and if someone wants it repeated, repeat it exactly.
Open with one that catches everybody
Start in Warm ups, where the whole group walks into the same trap together. Being wrong in company is funny. Being the only one who is wrong is not, so leave the Logic and Hardest groups until people are laughing at themselves.
Give the answer before it gets tense
For the quick ones, wait for two or three guesses and then tell them. For the Hardest group, do the opposite and allow real thinking time, with paper. Either way, explain the trap as well as the answer, since the explanation is the part people repeat to someone else the next day.
Stop at five or six in a row
After a handful, people stop answering and start inspecting every word, and the game slows to a crawl. Mix the groups so that two questions with the same kind of catch never sit side by side, then put the list away while they still want one more.
Ways to run it
Around the table
Ask one person at a time and give them about ten seconds. If they walk into the trap, the next person may try before you reveal the answer. Whoever gets one right picks who is asked next, which keeps the quick players from answering everything.
In a group chat
Post a single question and ask people to send their answer before reading anyone else's. The Wordplay group and the letter-counting sentence work best in text. Most of the Out loud group does not survive being typed, because the reader can see the spelling and nobody can be made to chant.
With a class or a big family
Put the question where everyone can see or hear it and have each person write an answer down before anyone speaks. Then ask for a show of hands for each answer and reveal it. Writing first means the quiet ones commit to an answer too, and nobody can claim afterward that they knew.
Two teams
Split the room and give each side a reader. Teams take turns asking the other side a question, with one answer allowed after a short huddle. Score a point for a correct answer and a point to the asking side for every trap walked into, and play to seven.
Pass it on
Whoever is caught becomes the next asker and chooses the next question from the list. It suits long car rides and slow dinners, and it spreads the reading around so that one person is not the quizmaster all evening.
When it goes sideways
Someone has heard them all
Ask before you start whether anyone knows a lot of these, and make that person your second reader. If an answer is blurted out anyway, congratulate them and move to a group they are less likely to know. The Numbers and Hardest groups hold up best against people who have seen the classics.
The answer starts an argument
A few answers are jokes and not facts, such as the two sides of a circle. When someone makes a sound case for a different answer, give them the point. Being generous costs nothing, and digging in turns a game into a dispute about rules.
One person keeps getting caught
Trick questions reward suspicion more than cleverness, and whoever answers fastest is usually the first one caught. Say that out loud, then hand the list over and let that person do the asking for a while. Never keep score against one individual.
A child gets frustrated
Go back to Warm ups and give a hint after the first wrong guess. Better still, teach the child two or three questions and let them try them on the adults. Children enjoy catching a grown-up far more than they enjoy being caught.