Confusing Questions to Ask
This list is for anyone who wants confusing questions to ask people at dinner, in the back seat or in a group chat, where the fun is the argument and nobody is being set up. None of the 54 hides a right answer, which is what separates them from trick questions, and they are sorted by the way they confuse: Quick knots, Word tangles, Self-undoing, Paradoxes, Blurry lines and In your head. Open with a quick knot when the group is new to this, and go straight to Paradoxes for the person who claims nothing confuses them.
Want questions from the whole vault instead? Try the random question generator.
The questions
Each question, and why to ask it
Quick knots
If you expect the unexpected, is it still unexpected?
Why ask it
Say yes and you were never really expecting it; say no and the thing you expected was no longer the unexpected. The word is being asked to describe one event from both sides of your thinking about it. A good opener, since everyone gets it in two seconds and nobody gets out.
If everything is possible, is it possible for something to be impossible?
Why ask it
Yes means something is impossible, so not everything is possible. No means there is one thing that cannot happen, which comes to the same result. The slogan loses on both branches, so ask who in the group says it most.
Is time wasted if you enjoyed wasting it?
Why ask it
The knot is in 'wasted', which means spent on nothing worthwhile, while enjoyment is usually counted as worthwhile. Whoever answers has to pick one of the two meanings, so ask what they did last Sunday and whether they would call it a waste.
Nobody is perfect, and practice makes perfect. So why practice?
Why ask it
Two sayings that everyone accepts, and they cannot both be literally true. People escape by saying 'perfect' is loose in one of them, so make them say which one and watch the table split.
Isn't 'indescribable' a description?
Why ask it
A description that says no description is possible cancels itself the moment it works. The usual defense is that 'indescribable' only means hard to describe, at which point you ask them to go ahead and describe it.
Has anyone ever made it to tomorrow?
Why ask it
Every time you arrive it has turned into today, because 'tomorrow' is measured from wherever you happen to be standing, the way 'over there' is. The day is real enough and the name can never be reached. Try the same move on 'here' and see whether anybody can leave it.
What are you doing when you look down on people who judge others?
Why ask it
Judging them, which puts you in the group you were looking down on, which you would then have to look down on as well. There is no stable place to stand, only a choice about where to stop. Keep it general and do not let anyone name names.
You are in the middle of nowhere. How far away is the edge?
Why ask it
'Nowhere' is not a place, so it has no middle and no edge, yet the phrase works perfectly well and everyone has been there. Ask for the most middle-of-nowhere spot each person has stood in, which turns a dead end into stories.
Would anybody notice if all of time stopped for an hour and then started again?
Why ask it
Every clock, heartbeat and memory would stop with it, leaving nothing running to measure the gap. That opens the stranger follow-up: if a thing cannot be noticed even in principle, did it happen?
Word tangles
Why isn't 'phonetic' spelled the way it sounds?
Why ask it
There is a reason, since the spelling came along with the word from Greek, but a reason is not an excuse. The one word that names sounding-it-out fails its own test, and no explanation makes that stop being funny. Ask for other words that let themselves down, like 'lisp' and 'monosyllabic'.
What is another word for 'synonym'?
Why ask it
If one exists, the word proves its own point; if none does, the one word that ought to have a synonym is missing one. Somebody will look it up and offer a near match, and the argument about whether a near match counts is the real game.
What is the opposite of 'opposite'?
Why ask it
'Same' is what most people say, and it holds until you ask for the opposite of 'same' and they answer 'different'. Opposites are supposed to work in both directions, and this pair will not.
If the dictionary spelled a word wrong, who would catch it?
Why ask it
The dictionary is what you would check the word against, so the referee cannot be caught by its own rule book. In practice dictionaries can be compared with each other and with how people write. That sensible answer should be held back until the group has suffered a little.
How can a product be 'new' and 'improved' at the same time?
Why ask it
A new thing has nothing before it to improve on, and an improved thing is the old one again. The label means 'changed', and nobody at the table will be able to explain why it does not just say so.
If a 'near miss' nearly missed, what did it do?
Why ask it
Read literally, something that nearly missed must have hit. People defend the phrase by taking 'near' to mean 'close by' instead of 'almost', and then cannot say why 'near hit' sounds wrong for the very same event.
If you say 'no pun intended,' why did you point it out?
Why ask it
Pointing at the pun is an intention, so the disclaimer undoes itself as it is spoken. The only innocent reading is that you noticed halfway through the sentence, and then the question becomes why you did not simply keep going.
How do you give the advice 'never say never' without breaking it?
Why ask it
The advice breaks its own rule twice in three words, so nobody can pass it on without disobeying it. It is a breather after something heavy, and it starts a hunt for other advice with the same flaw, such as 'always avoid absolutes'.
When you say 'I'm speechless,' are you?
Why ask it
Not while saying it. The sentence can only be true if nobody speaks it, so each use is a small untruth the listener forgives at once. Ask what people really do when words fail them, because it is never announcing the fact.
Self-undoing
Is the answer to this question 'no'?
Why ask it
Answer no and you have given the right answer, which means the true answer was yes; answer yes and the answer is 'no' after all. Demand one word and refuse 'it depends', because this question has no outside facts to depend on.
'This sentence is false.' Is it true or false?
Why ask it
True makes it false and false makes it true, and it is about nothing but itself, so the world offers no way to check. This is the liar paradox, one of the oldest on record. The fair replies are 'neither' and 'it is not really saying anything', and each one starts a new argument.
If I tell you that everything I say is a lie, do you believe me?
Why ask it
It sounds like the same trap as 'This sentence is false' and it is not: the claim can simply be untrue, which only means the speaker tells the truth some of the time, just not now. Ask it straight after the liar sentence and see who notices that this one has a door.
A card reads 'the other side of this card is true' on the front and 'the other side of this card is false' on the back. Which side do you believe?
Why ask it
Trust the front and the back must be true, and the back says the front is false. Trust the back and the front is false, so the back is not true. Neither sentence mentions itself, which is why it is worth making for real with an index card and letting people turn it over.
Pinocchio says, 'My nose will grow right now.' Does it?
Why ask it
His nose grows only when he lies. So if it grows he told the truth and it had no business growing, and if it stays put he lied and it should have grown. Tell it as a story to younger kids, who tend to feel the unfairness before they can explain it.
You set out to fail at something and you pull it off. Did you succeed?
Why ask it
You succeeded at failing, which means you did not fail, which means you did not succeed at it either. The escape is to say there were two goals stacked on top of each other, so ask which of the two goes on the report card.
Is there an exception to the rule that every rule has an exception?
Why ask it
If the rule holds, it needs an exception of its own, and that would be a rule with no exceptions. If it has none, it is its own counterexample. The rule cannot be fully true on any reading, and people mind that more than they expect to.
A sign says 'Ignore this sign.' How do you obey it?
Why ask it
Reading it is already failing to ignore it, and ignoring it afterward is doing what it says, which is hardly ignoring it. Ask what the person who put it up could possibly have wanted; that is where the funny answers are.
If someone orders you to be spontaneous and you do it, were you spontaneous?
Why ask it
Acting on command is the opposite of spontaneous, and refusing is disobeying, so nobody who heard the order can follow it. The same shape turns up in 'just act natural' before a photo, which gives people a real case to argue from.
What is the most boring number, and is it still boring once it holds that title?
Why ask it
Being the most boring number is a fairly interesting thing to be, so the winner is disqualified and the title passes to the runner-up, which inherits the problem. Let people nominate real candidates first, because the paradox lands harder on someone who has already committed to 38.
Paradoxes
What happens when an unstoppable force meets an immovable object?
Why ask it
The question describes a world that cannot exist: if anything is truly unstoppable then nothing is immovable, and the other way around. So the honest reply is that one of the two was mislabeled, and the fun is making people choose which.
A barber shaves everyone in town who does not shave themselves, and no one else. Who shaves the barber?
Why ask it
A barber who shaves himself is someone the rule forbids him to shave, and a barber who does not is exactly who he has to shave. Dodges like 'the barber is bald' fail because the rule covers everyone in town. The only way out is that no such barber can exist, which feels like cheating until you notice the story never showed that he did.
A teacher promises a surprise quiz one day next week. Can it ever be a surprise?
Why ask it
It cannot be Friday, because by Thursday night the class would know; with Friday out, Thursday falls the same way, and so on back to Monday. Having proved that no quiz can surprise them, the class is then surprised on Wednesday. Something in the proof is wrong, and people who study logic still argue about which step.
Could someone who can do anything build a wall too high for them to climb?
Why ask it
Yes leaves a wall they cannot climb and no leaves a wall they cannot build, so 'can do anything' fails on both sides. Most ways out trim 'anything' down to 'anything that makes sense', and the argument is over who gets to do the trimming.
To cross a room you must first cross half of it, then half of what is left, then half of that. How do you ever reach the far wall?
Why ask it
There is always one more half to go, so the list of steps never ends, and yet you arrive every time. Mathematics has an answer (endlessly many shrinking pieces can add up to a finite distance), though knowing it rarely makes the feeling go away. Have someone narrate the halves while walking across the actual room.
An older you travels back in time and hands your younger self a finished song. You grow up, become known for it, then go back and hand it over. Who wrote it?
Why ask it
Nobody did: every copy came from an earlier copy, and the loop has no first note. Unlike most time travel puzzles, nothing here contradicts anything else, which is the uncomfortable part. The song has no author and no one can say what rule that breaks.
A crocodile grabs your hat and says, 'You get it back if you correctly guess what I will do with it.' You say, 'You will keep it.' What happens next?
Why ask it
Keeping the hat makes your guess right, so the crocodile owes you the hat; handing it over makes your guess wrong, so it should have kept it. The promise cannot be kept in either case. Follow up by asking what happens if you guess 'you will give it back', which lets the crocodile off completely.
A hungry donkey stands exactly halfway between two identical piles of hay. Which one does it eat?
Why ask it
With nothing to tip the choice, any reason for going left is an equally good reason for going right, so a creature that acted only on reasons would stand there and starve. Real donkeys just eat. Ask what breaks the tie when the person answering faces two equal options, because 'I just pick' is harder to explain than it sounds.
If you pick an answer to this question at random, what is the chance you are right: A) 25%, B) 50%, C) 60% or D) 25%?
Why ask it
One in four says 25%, but 25% is listed twice, which makes it 50%, and 50% is listed once, which is back to 25%. No option agrees with itself, and the neat way out (zero, since none is right) works only because zero is not on the list. Best typed into a group chat, where people can stare at the four choices.
Blurry lines
One grain of sand is not a heap, and adding a single grain never turns a non-heap into a heap. So where do heaps come from?
Why ask it
Both statements sound true, and together they prove heaps are impossible while every beach says otherwise. Nobody has found the grain where it tips, because 'heap' was never built to be that exact. Ask for a number anyway, then take one grain away from it.
A band replaces its members one at a time until none of the founders is left. Is it still the same band?
Why ask it
Yes, because there was never a day it stopped being that band; no, because nobody who made the first record is on the stage. Each answer counts a different thing as the band (the name, the people, the songs) and nothing forces the choice. Real examples come up fast, so let people argue from the ones they know.
When you finish eating a donut, where does the hole go?
Why ask it
A hole is made of nothing, so there was nothing to go anywhere, yet it was plainly there a minute ago with room for a finger. The trouble is that we point at holes and count them as if they were objects. Best asked while someone is holding a donut.
How high do you have to climb before you are in the sky?
Why ask it
The sky has no floor: the air at your ankles is the same stuff as the air around a cloud. So you are either already in it or it starts at a height nobody can name. Small children often answer this with more confidence than adults, which is worth seeing.
What is north of the North Pole?
Why ask it
The question is perfectly grammatical and has nothing behind it, because at the pole every direction you can face is south. People reach for 'up' or 'space', which changes the subject. Use it as a model for other questions that sound deep and may be empty, such as what happened before time began.
If you forward a photo to five people, which copy is the original?
Why ask it
When the copies are identical, 'original' can only mean the one that came first, and nothing in the picture shows which that was. With a painting the question has an answer. With a file it may not even have a meaning, and somebody will insist it is 'the one on my phone' without being able to say why.
Is the pause in the middle of a song part of the song?
Why ask it
Take the pause out and the song is different, so it belongs to the song; but a pause is no sound at all, and a song is made of sound. One of those has to give and neither will. Clap a rhythm with a gap in it and ask whether the gap was clapped.
What color is your shirt when the lights are off?
Why ask it
The same color, because nothing about the shirt changed; no color, because color has to be seen. Both replies are right about different things, one about the cloth and one about the seeing, and the question refuses to say which it means.
When does a pen you borrowed become your pen?
Why ask it
Not on the day you took it, and not today either, although it has lived in your bag for a year and its owner has forgotten it. No moment in between can be pointed to, only a slow drift from one word to the other. Expect confessions, and possibly the return of a pen.
In your head
Try to think about nothing for five seconds. What were you thinking about?
Why ask it
Checking whether you are thinking about nothing is a thought, so the attempt reports its own failure. Anyone who claims to have managed it is describing what it was like, and that description was a thought as well. Count the five seconds out loud so the whole group tries together.
How would you know if you had forgotten something for good?
Why ask it
You would look for the memory and find nothing, which is also what you would find if the thing had never happened. From the inside the two cases are identical. A gentler follow-up: what has someone reminded you of that you would have sworn never took place?
When you talk to yourself in your head, who is listening?
Why ask it
If the listener is you, you already knew what was coming and had no need to say it; if it is someone else, there are two of you. Some people say they have no inner voice at all, so ask that first and expect the two camps to stare at each other.
If your red looked the way my green looks to me, how would we ever find out?
Why ask it
We would both point at a strawberry and say 'red', because each of us learned the word from the same objects. Every test anyone suggests uses words or matching, and both come out the same for the two of you. With no test available, it is unclear what a right answer would even look like.
Can you plan a surprise for yourself?
Why ask it
To plan it you have to know it, and what you know cannot surprise you. Somebody will suggest hiding a note and waiting to forget, which works only by splitting you into the person who hid it and the person who finds it. Ask whether that counts.
If your brain were making mistakes, what would you use to catch them?
Why ask it
The same brain, which is like asking a ruler to measure whether it has shrunk. Other people and written notes help, but you still judge those with the mind in question. Keep it playful: the point is the loop, not anybody's actual memory.
At what moment did you fall asleep last night?
Why ask it
You were there for it and still cannot say, since noticing the moment would mean being awake for it. The best anyone can give is a time they were still up and a time they woke. Everyone in the room has done this thousands of times and nobody has one eyewitness report.
What does it feel like to not notice something?
Why ask it
Any honest description would require noticing the thing, and then it is the wrong experience. The only answer is 'like nothing', which is also how everything you are missing at this moment feels. Good for ending a round, since people go quiet and start looking around the room.
How to confuse a room and keep it friendly
Practical guidance for the conversation itself
Asking so the knot holds
Read it exactly as written
These questions live in their wording. Paraphrase the card question, the crocodile or the multiple choice one and the knot usually falls open, so read from the screen and do not improve it on the way.
Get one word before any explaining
Ask for yes or no first, then why. Committing is what makes the trap close. A person who is allowed to open with 'well, it depends' walks around the question and never feels it.
Take the other side, whichever it is
Most of these have two answers that each defeat themselves. When someone says yes, argue no, and when they switch, switch with them. You are not being difficult. You are showing them the second wall.
Know which ones have a door
A handful can be escaped: the speaker who says everything is a lie, the room crossed in halves, the multiple choice question, the misspelled dictionary. Hold the exit back for a minute and then give it. Withholding it all evening stops being a game.
What kind of confusing each group is
Say up front that there is no catch
A trick question has a hidden right answer that you reveal at the end. Nothing on this page works that way. Tell the group before the first one that nobody is being fooled and nobody will be told they were wrong, or the people who hate being caught out will sit on their hands.
Loops, clashes and blurs
Self-undoing questions loop: whichever answer you give flips into the other. Paradoxes clash: two things that both sound true cannot both be. Blurry lines blur: a word everyone uses turns out to have no edge. Telling a frustrated person which of the three they are stuck in is often all the help they want.
Empty questions count as solved
A few questions are grammatical and ask about nothing: north of the North Pole, the edge of nowhere, where the donut hole went. Anyone who says 'that question does not mean anything' and can say why has given the best available answer, so treat it as a win and not as a refusal to play.
Word tangles are the rest stop
The language questions are lighter than the rest because the confusion belongs to English and not to the person answering. Go back to them when the table has had one paradox too many.
Group chat, dinner table, back seat
Dropped into a group chat
Post one question with no comment and leave. The ones that need rereading do best in text: the multiple choice question, 'Is the answer to this question no?', the opposite of 'opposite'. Do not explain for at least an hour, and let the first person who cracks do it for you.
Around a table
Quick knots and Blurry lines suit a table because people can interrupt each other. Props help more than you would think: an actual donut, an index card written on both sides, a pen of doubtful ownership.
With kids in the car
Pinocchio, the crocodile, the sky and the donut hole all work as short stories. Say at the start that these are questions grown-ups cannot answer either. A child who expects a right answer and never gets one feels cheated, and a child who has been told there is none feels let in on something.
One on one
With a single person the In your head group works best, since the questions ask them to check something privately and report back. Leave long silences alone. They are doing the experiment.
When to let one go
Someone is annoyed, not amused
Some people find a question with no answer restful and some find it an itch they cannot reach. If a face has gone tight, give them one that has a door, tell them the exit, and move to Word tangles.
Someone announces they have solved it
Hear the whole solution out. Often they have found a real exit, usually by pinning down one slippery word, and they deserve to be told so. If the fix only moves the problem, ask the same question about their new version and let them find that out for themselves.
Three or four is a full round
Being confused is tiring in a way that laughing is not. Stop while people are still arguing about the last one, because that argument will carry on without you, which is the result you were after.