Stupidest Questions to Ask
Questions with no useful answer, which is the point. Built for waiting rooms, long car journeys, and groups where nobody wants to talk about work, and none of them require knowing anyone well.
The questions
Open any question for the note
If you had to rename the moon, what would you call it?
Why ask it
Immediate and impossible to get wrong, so it works with strangers. First answers are throwaway jokes and second answers are better, so ask for another one.
Is a hot dog a sandwich?
Why ask it
A famously unresolvable argument, which is the entire function. Useful early because it gets people talking to each other instead of answering whoever asked.
If you could delete one food from existence, what goes?
Why ask it
Destructive choices produce stronger opinions than favorites do. Somebody will defend olives with genuine feeling and somebody else will take it personally.
What's a job you'd be catastrophically bad at?
Why ask it
Sounds like a joke and produces oddly accurate self-assessment. The reasons people give are funnier than the jobs they name.
If your pet could talk, what's the first complaint?
Why ask it
Owners answer this in character, which is consistently funnier than anything they would say as themselves. People without pets can borrow someone else's.
What's the correct number of pillows?
Why ask it
Domestic absurdities divide a room faster than politics. Ask people to justify their number and the argument escalates without any help from you.
If you could win one argument permanently, which argument?
Why ask it
Framed as a joke, and the answers quietly reveal what people are tired of arguing about at home or at work. The specificity is what gets the laugh.
What's the most ridiculous thing you own?
Why ask it
Objects beat opinions, and most people can produce theirs in about a minute. If they claim they own nothing ridiculous, ask about their kitchen drawer.
If you came back as a piece of furniture, what are you?
Why ask it
Everyone's answer is a self-portrait they did not intend to paint, so the follow-up question about why is where this actually pays off.
What's the worst possible thing to say in a wedding speech?
Why ask it
Invention with a clear target, so answers escalate fast. Somebody in the room will admit to having nearly said theirs out loud.
If you had to get everywhere by one ridiculous form of transport, what is it?
Why ask it
Loose enough that people build the joke themselves. The answers that get into logistics, tunnels, catapults, running costs, are the ones to keep pulling on.
What food combination will you defend in public?
Why ask it
Shifts from hypothetical to confession while staying completely trivial. Anyone who claims to have none is holding something back and the table will find it.
If animals had a legal system, which animal is the lawyer?
Why ask it
Absurd but specific, and the reasoning matters more than the choice. Crows do unreasonably well in most rooms.
What would your reality show be called?
Why ask it
Forces a title, and titles are compact jokes. If somebody undersells it, ask what happens in episode one.
What's the dumbest thing you've ever won?
Why ask it
Small victories with a trophy attached make far better stories than real achievements. Raffles and pub quizzes supply most of them.
If you had to hide a spare key somewhere ridiculous, where?
Why ask it
A joke with a practical layer, and someone always volunteers their real hiding place, which the rest of the group then reviews harshly.
What's the most unnecessary thing you've ever felt strongly about?
Why ask it
Invites people to indict themselves, gently. Answers tend to involve tea, seating arrangements, or the correct way to load a dishwasher.
If you could make one very small thing illegal, what is it?
Why ask it
The word small keeps it funny instead of political. The enforcement details are where everyone else joins in.
What's a rule you follow that nobody asked you to?
Why ask it
Sounds absurd and lands on something genuinely revealing: private routines people have never had a reason to describe out loud.
What's the stupidest question anyone has ever asked you?
Why ask it
Hands the floor back at the end, and it usually produces a story about a job interview, a customer, or a relative at a family gathering.
How to use these questions
Practical guidance for the conversation itself
Making a stupid question work
Deliver it flat
Asked with a straight face, an absurd question gets a real answer. Asked with a wink, it gets a shrug, because you have already told everyone it does not matter.
Take the first answer seriously
Following up on a ridiculous answer as though it were a policy proposal is where most of the comedy comes from. Ask about costs, logistics, and enforcement.
Move on while it is still funny
Two or three of these, then back to normal conversation. A whole evening of absurd hypotheticals turns into homework.
Where these work
- Car journeys and waiting rooms, where nobody can leave and there is nothing else to look at.
- Groups that do not know each other well, since none of these require a personal history to answer.
- With children and teenagers, who tend to give better answers than adults and enforce the rules more strictly.
- Not in a meeting billed as an icebreaker, where hypotheticals with no answer usually irritate whoever wanted to get on with the agenda.
Common pitfalls
Explaining the joke
If a question needs setup, it has stopped being a stupid question and become an anecdote. Ask it cold or not at all.
Letting one person win
The argumentative questions are meant to stay open. If somebody is producing evidence on their phone, change question rather than resolving it.
Reaching for something edgier when a question flops
Not every question lands with every group. Move to the next one instead of escalating, because escalation is how these evenings go wrong.
Asking a group that wants a real conversation
Absurd questions cannot rescue a conversation that people want to be serious. If two people are mid-topic, leave them to it.