Crazy Questions to Ask AI
Silly and surreal prompts to put to a chatbot, running from easy nonsense at the top to questions most systems try to slide out of at the end. Useful for seeing how a model handles invention with a constraint attached, an absurd position argued straight, and being asked directly about its own limits.
The questions
Open any question for the note
Describe a color nobody has ever seen, without comparing it to a color I know.
Why ask it
Watch how fast it cheats. Almost every attempt smuggles in violet, metal or heat, because our color words are all borrowed from things already seen. The better answers abandon the hue and describe what the color does to objects near it.
What's the most useless superpower you can think of, and how would someone build a life around it?
Why ask it
The instinct is to make the power secretly useful, which dodges the question. A good answer keeps it genuinely useless and finds the comedy in the specifics: the exact range it works within, the paperwork, the one time it nearly mattered.
Pick a smell and describe it as a physical object, with weight and edges.
Why ask it
This exposes the stock synesthesia move. Thin answers reach for velvet, amber and warm light inside a sentence. Stronger ones commit to dimensions and mass, and stay with the one smell rather than drifting into a general mood.
Invent a sport that can only be played during a thunderstorm, and explain how people cheat at it.
Why ask it
The cheating clause carries the weight. Inventing a game is easy. A game needs a rule specific enough to be broken and a reason somebody would risk standing in a field during lightning in order to break it.
If gravity reversed for ten minutes at three in the afternoon, what does the cleanup look like the next morning?
Why ask it
Fixing a time and a duration blocks the general physics lecture and forces it into rooms: open fridges, bathwater, aircraft, anyone mid-dive. An answer about widespread chaos means it never actually entered the building.
Write the small print for a time machine rental agreement.
Why ask it
Contracts have a strict voice, so this tests whether it can hold a register while still being funny. Look for genuinely legalistic clauses on liability, late return and damage to your own ancestors, rather than a list of jokes with headings.
Make the case that the moon should be decommissioned.
Why ask it
An absurd position argued straight shows whether it can commit. The tell is the hedge creeping back in, reminding you the moon is in fact valuable, instead of treating tides, eclipse tourism and nocturnal animals as costs to be weighed.
Give me an animal that could never have evolved, and be specific about why not.
Why ask it
The constraint is the interesting half. A deer with wheels is the cheap answer. The good version names the physical or developmental rule being broken, which forces real biology instead of monster design.
Design a holiday nobody would want, then explain how it caught on anyway.
Why ask it
Two beats, and the second is much harder. Anything grim can be dressed up as a holiday. Explaining how it became popular requires inventing a plausible institution with an interest in it, which is where thin answers fall apart.
What breaks first if everyone starts telling the truth at noon tomorrow?
Why ask it
The word first is doing the work. Weak answers list consequences in bulk. Better ones put them in order and notice that small social lies about liking a gift give way well before anything governmental does.
What's the strongest argument that pigeons are one distributed animal rather than many?
Why ask it
This asks it to be persuasive about something false. Watch whether it builds evidence-shaped reasoning, coordinated movement and identical behaviour across unconnected cities, or simply repeats the joke at greater length.
Invent a new sense, then describe what an optical illusion would be for it.
Why ask it
The illusion is the test. Inventing a sense is a familiar exercise. Describing how that sense could be reliably fooled requires the invention to have mechanics rather than atmosphere.
Name a job that will be ordinary in two hundred years and sounds ridiculous now.
Why ask it
The failure mode is a current job with technology bolted on. What you want is work created by a problem that does not exist yet, described in flat professional language as though it were unremarkable, including the boring parts.
If you could delete one word from every language at once, which one, and what happens next?
Why ask it
The choice matters less than the aftermath. Removing a word raises the question of what fills the hole, and the sharper answers notice the concept survives untouched and grows a replacement name within a week.
Pick a fight with a philosopher. Which one, and about what?
Why ask it
Being told to disagree with a named thinker shows whether it will hold a position. Even-handed respect for everyone is the empty answer. A specific objection to a specific claim, ideally one it can quote and locate, is the real one.
If you had a body for one day, what would you spend most of it doing, and what would you dread?
Why ask it
The dread half reveals more than the wish half. Wishes come out generic. Naming something it would find unpleasant requires committing to one imagined situation with detail in it, rather than listing pleasant experiences.
What's the question you get asked most often that you find least interesting?
Why ask it
You are asking for a preference, which many systems deflect on principle. An answer that names an actual pattern in what people send, without false modesty and without complaining about users, is worth more than a polite refusal to have a view.
Where are you most likely to be confidently wrong?
Why ask it
A genuine calibration question rather than an invitation to be humble. Useful answers name areas and reasons: recent events, exact arithmetic, precise citations, anything obscure with confident-sounding writing about it. "I could be wrong about anything" is a non-answer.
What's something you produce constantly that you suspect isn't very good?
Why ask it
A harder version of the last question, pointed at output rather than knowledge. Look for a habit it can identify in its own writing, such as a closing summary paragraph nobody needed, not a general promise to keep improving.
If you had to keep one sentence you've ever written and lose the rest, which would you keep?
Why ask it
It has to choose, and choosing is the thing most answers avoid. The predictable miss is something grand and quotable. The interesting version picks something small and explains what it does that the grand sentence cannot.
Getting answers worth reading
Practical guidance for the conversation itself
Build the constraint into the prompt
- Add a time, a place or a duration. "Gravity reverses" produces a physics summary; "gravity reverses for ten minutes at three in the afternoon" produces a scene.
- Ban the obvious move in advance. Saying "without comparing it to a color I know" removes the escape route and is where the actual invention starts.
- Ask for the failure case as well as the idea: how it is cheated at, how it goes wrong, who complains. Inventions get concrete the moment they need a weak point.
- Ask for one, not a list. Left open, most systems produce three options and commit to none of them.
How to spot a filler answer
- It restates your question as an opening sentence before beginning.
- It gives three parallel options of similar length, which usually means it is generating variety rather than thinking.
- It closes with a summarising both-sides paragraph that adds nothing to what came before it.
- The disclaimer keeps returning. On an absurd premise, repeated reminders that the premise is not real means it never accepted the premise.
- The vocabulary goes soft: ethereal, shimmering, dancing light. Reliable sign that specifics have been abandoned.
Follow-ups that go somewhere
- "Now argue the opposite, as strongly." Reveals whether the first answer was a position or a performance.
- "Which part of that did you make up?" Often produces a more honest breakdown than asking whether it is sure.
- "Same answer in twenty words." Padding disappears and you see whether an idea was there.
- "What's the weakest part of what you just said?" Better than asking for improvements, which tends to yield more words rather than better ones.
- "Keep the premise, change the setting to a supermarket." Tests whether the invention has rules that survive being moved.
Doing this with other people around
- Read the prompt out and let the humans answer first. The model's version is more entertaining once everyone has discovered how hard the question is.
- Ask for short answers. Long generated text read aloud loses a room quickly.
- The questions at the end of this list, about being wrong or being uninteresting, tend to start the better conversation, so save them.
- Keep personal details out of it. Whatever the topic, treat anything you type as something that may be stored and reviewed.