Dumb Questions to Ask Your Friends to Annoy Them
Dumb questions annoy a friend best when they sound sincere: the square root of a sandwich, or a favorite number between 1 and 0, asked in a flat voice by someone who seems to want an answer. If you came looking for troll questions to ask, these 57 questions are the harmless kind, grouped by how the wind-up works: Fake trivia, Nonsense, Old debates, No context, Follow-ups and Over text. Deploy sparingly, and only on people who like you.
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The questions
Each question, and why to ask it
Fake trivia
What's the square root of a sandwich?
Why ask it
The grammar is fine and the request is not, so a friend's brain starts on it before it objects. If they say half a sandwich, ask them to show their work.
What's your favorite number between 1 and 0?
Why ask it
The trap is the ordering, not the range. People start answering before they notice, then have to decide whether to correct you.
What's the speed of dark?
Why ask it
Someone will confidently say it travels at the speed of light, someone else will say dark is not a thing that moves, and the two of them will forget you were involved.
What's the difference between a duck?
Why ask it
An old anti-joke that stops one word early, so the listener waits for the rest of the sentence. When they ask 'a duck and what?', say 'just the duck' and hold eye contact.
How much does a thought weigh?
Why ask it
The one question in this group that can go somewhere by accident. A friend who starts on brain cells and electricity is giving a lecture, so nod, and ask whether a sad thought weighs more.
What's north of up?
Why ask it
It has the shape of a riddle with a solution, and that keeps a friend working at it. Whoever answers 'nothing' has understood it and will be irritated that there was nothing to get.
Is it farther to the airport or by bus?
Why ask it
Two halves of two sensible questions, joined in the middle. Thank the friend who says 'by bus' as though that settles your plans, and repeat it more slowly for the one who asks 'farther than what?'.
What comes after the last number?
Why ask it
Do not accept infinity: tell them infinity is not a number and ask again. Of everything in this group, this is the one most likely to get you told to stop.
Which is heavier, a kilogram of regret or a kilogram of feathers?
Why ask it
Built to catch anyone who has heard the bricks-and-feathers version and answers on autopilot. Wait for the pause when they realize one of the two cannot go on a scale.
What's half of a hole?
Why ask it
Half a hole is still a whole hole, which people work out about two seconds after saying 'a smaller hole'. Agree with their answer and then ask where the other half went.
How far is it from here to Thursday?
Why ask it
Distance and time are swapped, so the sentence parses and means nothing. If they answer in days, ask for it in miles.
What's the capital of the alphabet?
Why ask it
It sounds like geography, so they hunt for a place before settling on the letter A. Tell them that was close and decline to say what the answer is.
Nonsense
If the color beige had a middle name, what would it be?
Why ask it
Beige invites a mild contempt, so the names come out dull on purpose. Write the answer down as though it will be needed later.
What does Tuesday smell like?
Why ask it
Some people have an immediate answer and cannot explain why, which unsettles the rest of the group more than the question does.
What's the loudest color?
Why ask it
The answer comes fast and the reasons never do, which leaves two friends who picked different colors with nothing to argue with but volume. Tell whoever says red that red is the quiet one.
If silence had a flavor, would you order it again?
Why ask it
The yes-or-no framing is the irritant, because it demands a verdict on a premise nobody agreed to. Follow-up: ask what it came with.
If your left shoe had a vote, what would it ban?
Why ask it
Puddles, stairs and the right shoe all have a case. Anyone who asks why it is the left one has taken the bait, and the reply is that the right shoe abstained.
Which kitchen appliance would file a complaint about your personality?
Why ask it
The joke points at the person answering, so they play along where a dig from you would get a groan. Ask for the wording of the complaint: a toaster tired of being ignored until something burns is the standard to beat.
How would you explain the letter M to someone who had only ever heard of N?
Why ask it
The setup is impossible but the task feels solvable, so people try in earnest. Time how long it takes before someone draws it in the air.
Which month is the most left-handed?
Why ask it
Nobody has an opinion on this until asked, and then they will defend their month as though it were obvious. Put the same question to the next person so the two answers can disagree.
Which vegetable is hiding something?
Why ask it
Treat whatever they name as an accusation: ask what it did and who else knows. A friend who says celery without a pause has clearly thought about this before.
Which of your fingers do you trust the least?
Why ask it
They will look at their hand before answering, and from that moment they are taking it seriously. The ring finger is the easy target, having no clear job.
Who wins an argument, a staircase or a ladder?
Why ask it
The staircase has stability and the ladder has ambition, and somebody will say so with a straight face. Refuse to accept a draw.
Old debates
Is a hot dog a sandwich, and can you answer without raising your voice?
Why ask it
There are real sides to this one, so it will outlast the joke by an hour. The second clause is what makes it unbearable, because people cannot help proving it wrong.
How many holes does a straw have?
Why ask it
One or two, and both camps think the other is being deliberately obtuse. Nobody changes their mind, so pick the smaller camp at the table and join it.
Is water wet, and are you prepared to be wrong?
Why ask it
People arrive with a rehearsed position on this one because it has circulated online for years. The annoying part arrives later, when they are still arguing it after you have lost interest.
How long is a piece of string, to the nearest inch?
Why ask it
The phrase is the stock way of saying nobody can know, and asking for inches takes that exit away. Anyone who gives you a real number has won and should be congratulated.
Is it pronounced GIF or GIF?
Why ask it
Out loud only. Say the word exactly the same way both times and keep a straight face while they try to work out which one you want them to pick.
Is a Pop-Tart a ravioli, yes or no, no explaining?
Why ask it
Filling sealed inside a pastry shell is the entire case, and it is stronger than anyone wants it to be. With explaining banned, count how many words past 'no' a friend gets before you hold up a hand.
Is a thumb a finger, and how many fingers am I holding up?
Why ask it
Ask the first half, let them commit, then hold up an open hand. Whichever they said, four or five, the other number is now yours to insist on.
How many is a few, and why isn't it three?
Why ask it
Most people carry a private number for a few, a couple and several without ever having compared notes. Reject the number they give, then ask how many several is.
Do you put on both socks first or finish one foot at a time, and why is that the wrong way?
Why ask it
Sock, sock, shoe, shoe people have rarely pictured the alternative, and hearing it described bothers them. The last clause rules against them before they have answered, so the defense starts early.
No context
What's the third thing?
Why ask it
Asked with no context and complete confidence, as though you are following up. A friend will search their memory for a list they never heard, and when they offer two things, repeat the question.
Have you noticed it yet?
Why ask it
There is nothing to notice. They will check the room, their shirt and your face, and 'never mind, you will' keeps it running for the rest of the afternoon.
So, did you ever hear back?
Why ask it
Nearly everyone is waiting to hear back from someone, so the question finds its own target. Nod at whatever they tell you, then say 'no, the other one'.
Is this the one you were telling me about?
Why ask it
Ask it while holding up something ordinary: a fork, a remote, their own water bottle. The more certain you sound, the longer they wonder whether they did once tell you about a fork.
Why were you so rude to me in my dream last night?
Why ask it
Holding a friend to account for a dream they were not present for is unfair in a way that is hard to argue with. Accept the apology and stay vague about what they did.
What were you about to say?
Why ask it
Best asked into a silence where they were plainly about to say nothing. Plenty of people produce a sentence anyway, just to be helpful.
Can I ask you a question?
Why ask it
When they say yes, thank them and walk away, because that was the question. It works once per friend, so choose the friend.
Wait, was that today?
Why ask it
Said with a small amount of alarm and no further detail. Own up within a minute, since a friend who really has forgotten something will start to worry.
You know what I mean?
Why ask it
Ask it after saying nothing at all, ideally following a long pause. A friend who answers 'yes, completely' has outplayed you and should be allowed to enjoy it.
Follow-ups
Are you sure?
Why ask it
Two words that work on any answer to anything, including their own name. Use it once per answer; a second time is just badgering.
Can you be more specific?
Why ask it
Meant for answers that could not possibly be more specific, such as 'four' or 'no'. Stay polite, as though a little more detail would clear everything up.
And then what?
Why ask it
Use it on an answer that was not a story. If beige's middle name is Gary, ask what happened next, and enjoy the pause while they look for an event.
Compared to what?
Why ask it
For answers that compared nothing, such as a name or a vegetable. 'Celery.' 'Compared to what?' leaves a friend defending celery against everything else at once.
On a scale of one to ten?
Why ask it
Leave off what is being measured. If a number comes back before 'of what?' does, thank them for their honesty and never say what the scale was for.
Is that a yes or a no?
Why ask it
Reserved for questions that were never yes or no, like what Tuesday smells like. Insist on one of the two until a reasonable person says 'yes' to a smell.
Okay, but why?
Why ask it
The toddler's method, and it still works on adults. Three in a row is the limit: by then a friend answers 'because I said so', has turned into their own parent, and you can stop.
Who told you that?
Why ask it
It treats their opinion about the loudest color as a rumor they picked up somewhere. Watch them try to name a source before remembering they made it up ten seconds ago.
Over text
Are you awake?
Why ask it
Send it at two in the afternoon. Any reply answers it, so what usually comes back is a single question mark, and that counts as a win.
Did you get this message?
Why ask it
It can only be answered by someone who did. A friend who replies 'no' is playing along, so say you will resend it and send the same message again.
What's your number again?
Why ask it
Sent by text, to the number in question. The patient friends type it out in full before they see what they are doing.
Guess what?
Why ask it
Whatever they reply, including 'what?', answer 'no, guess'. Two rounds is funny and a third costs goodwill, so have something real to tell them by then, even if it is only what you had for lunch.
Which one?
Why ask it
Send it with no photo, no link and no earlier message it could refer to. A committed friend will answer 'the left one', and then you owe them a 'good choice'.
Is your phone on silent?
Why ask it
If they see it, the answer hardly matters, and if they do not, they cannot reply. It is at its best sent to a friend sitting across the same room.
Are you free that day?
Why ask it
No day has been mentioned, and a friend will scroll up to make sure. Follow it with a real plan, because this one is only funny coming from someone who does eventually name a day.
Sorry, who is this?
Why ask it
Send it first, to a friend who has not messaged you all day. They will point out that you texted them, and 'that doesn't answer my question' is the reply.
How to Do This Without Losing Friends
Practical guidance for the conversation itself
Which group to pull from
Fake trivia and Nonsense for a bored room
Fake trivia sounds like a sum or a quiz question and has no answer, and the Nonsense group asks for an opinion nobody holds. Both suit a table or a car full of people, since anyone can answer and no one is singled out.
Old debates when you want them arguing with each other
The hot dog, the straw and the Pop-Tart arrive with sides already attached. Ask one, add the extra clause that makes it worse, and your part is finished.
No context for one friend at a time
The third thing and the dream question depend on a friend trying to remember a conversation that never happened. In a group someone laughs and gives it away, so save these for one to one.
Follow-ups go on top of an answer
Nothing in the Follow-ups group starts a conversation. Each one is a reply to what your friend just said, about beige or the straw or anything else, and one per answer is the dose.
Over text when you are not in the room
Most of these are sent to one friend with nothing before or after them, and 'What's your number again?' only works in a private thread. A message cannot carry a straight face, so admit the joke sooner than you would in person.
Who and when
Only with people who already find you funny
The same question is a bit or an insult depending on the relationship. With someone new, deliberate nonsense reads as not listening.
Never while they are doing something
Mid-task, driving in traffic, or on the phone, these stop being funny immediately. The right moment is when everyone is already bored and there is nothing else happening.
Two or three, not the whole list
The joke depends on the question arriving out of nowhere. Working down a list turns it into a bit everyone can see coming, and it stops landing after the third.
Delivery
- Ask in a completely flat, sincere voice. Signalling that you know it is nonsense removes the whole effect.
- Do not explain the joke when they push back. Repeat the question instead, in the same voice.
- The first question only sets it up. 'Can you be more specific?' on top of a one-word answer does the annoying.
- Let two of them start arguing with each other and go quiet. That is the best outcome available.
- Have one question with real sides ready, such as the straw or the socks, so you can pivot if the mood turns.
Knowing when to stop
When someone stops answering
Short flat replies mean the game is over for them. Past that point only one of you is in on the joke, so answer the next thing they say like a normal person.
When it turns into a real argument
The hot dog and straw questions have actual sides, and they can curdle. Concede the point cheerfully and change the subject.
When it is aimed at one person
The square root of a sandwich asked of a whole table is nonsense. Asked of the same friend five times in front of the others, it is about that friend, so spread the questions around or drop them.
When a text gets no reply
A friend's silence in a chat cannot be read the way a flat voice can. Send one line saying it was a joke about nothing and leave it there.