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02 · Social & Fun

Dumb Questions to Ask Your Friends to Annoy Them

Twenty nonsense questions designed to be mildly infuriating, like asking for the square root of a sandwich or a favorite number between 1 and 0. There are no right answers, which is the whole appeal. Deploy sparingly, and only on people who like you.

20 questions · each with a note on why · conversation guide

The questions

Open any question for the note

  1. What's the square root of a sandwich?

    Why ask it

    The reliable opener, because the sentence is grammatical and the request is not. Most people answer with half a sandwich, which is wrong in a way they cannot immediately explain, and that is the annoying part.

  2. 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, which is a more interesting fork than the question deserves.

  3. 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.

  4. How much does a thought weigh?

    Why ask it

    This is the one that accidentally goes somewhere. There is a real answer about the energy cost of neurons, so expect either a shrug or a lecture, with nothing in between.

  5. What's north of up?

    Why ask it

    Sounds like a riddle with a solution, which is what makes people keep working at it. Whoever answers nothing has understood it and will be irritated that there was nothing to get.

  6. Is a hot dog a sandwich, and can you answer without raising your voice?

    Why ask it

    The only question here with a genuine dispute behind it, so it will outlast the joke by an hour. The second clause is what makes it unbearable, because people cannot help proving it wrong.

  7. 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, which is the point of asking.

  8. If the color beige had a middle name, what would it be?

    Why ask it

    The answers are better than the question deserves, because beige invites a specific kind of contempt. Someone will name a relative.

  9. What does Tuesday smell like?

    Why ask it

    About a third of people have an immediate answer and cannot explain why, which unsettles the rest of the group more than the question does.

  10. 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. The pause when they realise one of the two is not a physical object is the whole payoff.

  11. If your left shoe could vote, who would it back?

    Why ask it

    Absurd enough to be safe, and it produces a surprisingly detailed character sketch of the shoe. Anyone who asks why the left one has taken the bait.

  12. How wide is a decision?

    Why ask it

    People try to answer it as a metaphor before conceding it is not one. The attempt to make it mean something is funnier than any answer.

  13. What comes after the last number?

    Why ask it

    Do not accept infinity, since infinity is not a number and saying so is the second half of the joke. This is the question most likely to get you told to stop.

  14. 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.

  15. What's the loudest color?

    Why ask it

    Almost everyone answers instantly and then argues about it, because the intuition is strong and completely unjustifiable. Red and neon yellow do most of the work.

  16. Which kitchen appliance would file a complaint about your personality?

    Why ask it

    The self-deprecating version of the appliance question, which is why it gets a real answer instead of a groan. The toaster comes up more than you would expect.

  17. 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 genuinely try. Watch how long it takes before someone draws it in the air.

  18. How long is a piece of string, and I want a number?

    Why ask it

    The stock non-answer is blocked by the second half, which is exactly why it annoys. Anyone who gives you a real number has won and should be congratulated.

  19. 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 annoyance is not the question, it is that they cannot let go of it afterwards.

  20. What's the third thing?

    Why ask it

    Asked with no context and complete confidence, as though you are following up. Most people search their memory for a list they never heard, which is the cheapest possible trick on this page.

How to Do This Without Losing Friends

Practical guidance for the conversation itself

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 twenty

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.
  • The follow-up is what actually annoys people: ask them to be more specific.
  • Let two of them start arguing with each other and go quiet. That is the best outcome available.
  • Have one real answer ready for a question like how much a thought weighs, 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. Continuing past that point stops being a joke you are both in on.

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

Repeatedly asking the same friend unanswerable questions in front of others stops being nonsense and starts being about them.