Dumbest Questions to Ask
Twenty questions with no possible answer: how to fold a cloud, how to weigh a shadow, which nonexistent day of the week is your favorite. Useful when a group has gone quiet and nobody wants another round of small talk.
The questions
Open any question for the note
What's the best way to fold a cloud?
Why ask it
The good answers treat it as a real technical problem and describe the equipment. Anyone who just says you cannot has opted out, so follow up by asking them to pretend they have already agreed to try.
How would you weigh a shadow?
Why ask it
Someone in the room will start explaining light and mass in earnest, and the group has to decide whether to let them. That fork is more entertaining than the question.
What's your favorite day of the week that doesn't exist?
Why ask it
Most people invent a name and then immediately assign it a mood and a place in the week, usually between Sunday and Monday. What they invent says more about their schedule than their imagination.
How would you catch a thought before it gets away?
Why ask it
This one quietly turns practical, because half the room actually has a method involving notes apps and voice memos. The joke becomes a real exchange of habits.
Which punctuation mark would other people say you already are?
Why ask it
Asking what others would say instead of what they would choose is what makes this work. Nobody picks a period for themselves, but plenty will admit others see one.
If you were a traffic light, which color would you be stuck on?
Why ask it
The word stuck is what gets the honest answer. People who pick amber are usually describing their whole approach to decisions and will notice as they say it.
What sound would your personality make?
Why ask it
Expect a demonstration rather than a description, which is the point. Anyone who names a musical instrument is flattering themselves and the group will say so.
What's the flavor of the number four?
Why ask it
Some people genuinely associate numbers with tastes and colors, and this question finds them. The rest of the room finds that far more unsettling than the nonsense.
What's the ninth color?
Why ask it
Sounds like it has an answer, so people count rainbows on their fingers before objecting. Whoever names a specific shade with confidence has understood the assignment.
If a doorknob could complain, what would it say about your house?
Why ask it
Reframing the absurd from the object's side gets a small tour of somebody's home life. The complaints are usually about a specific person who slams things.
If you had to be a vegetable, would you rather be a carrot or a cucumber?
Why ask it
A forced choice between two meaningless options, which produces more committed argument than an open question would. Nobody is neutral once they have picked.
How would you describe rain to someone who had only ever been indoors?
Why ask it
Starts as nonsense and turns into a genuine test of description. Watch for people who go straight to the smell rather than the water, because that answer is usually the best one.
If your handwriting had a voice, what would it sound like?
Why ask it
Everyone has an opinion about their own handwriting already, so the answers come fast and are unusually self-critical.
Which piece of furniture in your house is the most judgmental?
Why ask it
The answer is almost always the one associated with a chore nobody does. It is a way of asking what someone feels guilty about without asking that.
How would you measure a nap without using time?
Why ask it
People land on units like episodes, dreams, or how bad they feel afterwards. It gets more inventive than most questions on this page because the constraint is clear.
What's the shortest distance between two ideas?
Why ask it
The nonsense here is dressed as geometry, which is why people try to solve it. Answers about jokes or arguments usually beat answers about logic.
If you had to bottle a Sunday afternoon, what would the label say?
Why ask it
Whether the label is warm or bleak tells you what Sundays are like for that person. A surprising number are bleak, and that is worth noticing rather than laughing at.
What would you do with a Thursday that had no afternoon?
Why ask it
The impossible framing gets past the usual answer about catching up on sleep. People start describing what they would skip, which is more revealing than what they would do.
If you could argue with your reflection about one thing, what would it be?
Why ask it
This is the point where the round can turn sincere, so ask it late or not at all. If someone answers seriously, let the joke drop rather than rescuing it.
What's the last question anyone will ever ask?
Why ask it
A closing question that gets either a punchline or a long pause, and both are acceptable. Anyone who asks whether you mean the last person alive has taken it further than you did.
Using Questions With No Answers
Practical guidance for the conversation itself
Opening a round
Answer the first one yourself, badly
A weak answer from whoever asks sets the standard low enough for everyone else to join. Asking a question like this and then sitting back to evaluate answers kills the round immediately.
Start with a doing question, not a being question
How to fold a cloud gets a method. Which punctuation mark you are gets a judgment about your personality, which people are slower to volunteer to a group. Save those for later in the round.
Ask why once, then move on
One follow-up gets the reasoning, which is the funny part. Three follow-ups turn a joke into an interrogation and the next person will give a one-word answer.
Reading the group
Someone will try to solve them
In most groups one person answers the shadow question with actual physics. Let it happen for a minute, since it is usually interesting, then hand the round back to the next person.
Watch for the sincere answer
Every so often an absurd question gets a real one, particularly the Sunday afternoon and reflection questions. When that happens, do not immediately make a joke over the top of it.
Two or three people is a different game
In a small group these become a conversation and can run long. In a group of eight they need to move fast, one question and one answer each, or the people who are not answering check out.
Where these fit
- Dead time works best: waiting rooms, delayed trains, the half hour before food arrives.
- They are a poor icebreaker with strangers, because half of them need someone to already find you funny.
- With children they land better than with adults, and the answers are better too.
- In a work setting, stick to the object questions and skip anything about personality.
- Five or six is the limit. There is no version of this that survives twenty in a row.