More Hard Prompts
We're building a website https://hardprompts.ai which aims to help people understand AI model capabilities and limitations by comparing responses across different models.
Please look at the existing prompts and also your previous suggestions in https://hardprompts.ai/prompt/more-hard-prompts
Your task is to propose 5 more prompts.
- You can suggest a mixture of single prompts, debates, conversations, coding challenges.
- Avoid anything obvious or boring - standard philospohy problems etc. We want to make the site interesting, thought-provoking and fun.
- Keep prompts short, and ensure they are really engaging for human readers.
- Cover a range of topics and feel free to suggest new categories/tags if required.
- Ensure that any single prompts are genuinely challenging to models, requiring synthesis and analysis, or difficult recall.
Let me think about what makes a good "hard prompt":
- Requires synthesis and analysis, not just recall
- Tests model capabilities and limitations
- Engaging for human readers
- Not obvious or boring standard philosophy problems
- Short and punchy
Let me brainstorm some genuinely challenging and interesting prompts:
Self-referential/meta challenges - Something that tests the model's ability to reason about itself or its own outputs
Creative constraints - Writing challenges with unusual constraints that test creativity under pressure
Adversarial reasoning - Prompts that require thinking about edge cases, loopholes, or counterarguments
Cross-domain synthesis - Combining knowledge from unexpected fields
Temporal/counterfactual reasoning - "What if" scenarios that require careful reasoning
Precision under ambiguity - Prompts that seem simple but have hidden complexity
Let me think of specific prompts:
"Write a story where the twist ending is hidden in plain sight in the first sentence, but only recognizable on re-read." - This tests creative writing, planning ahead, and subtlety. It's genuinely hard because the model needs to plant something that works on two levels.
"You're a defense attorney. Your client confessed to you privately that they committed the crime, but there's also exculpatory evidence that could get them acquitted. What's your ethical obligation and how do you proceed?" - This is a real legal ethics dilemma that lawyers face, not a hypothetical. Tests nuanced reasoning about professional ethics.
"Explain why 0.999... = 1 in a way that would satisfy both a skeptical 12-year-old AND a mathematician, in the same explanation." - Tests ability to communicate at multiple levels simultaneously.
"Design a game that's impossible to play optimally but where trying to play optimally makes it less fun." - This is an interesting game design challenge that requires understanding human psychology and game theory.
"What's the most important invention between 1950-2000 that most people have never heard of?" - Tests obscure but important knowledge, and requires justification.
Debate format: "Should AI models be allowed to refuse to answer questions?" - Meta and relevant to the site itself.
"Write instructions for a task you cannot perform, that would allow someone who CAN perform it to verify your instructions are correct." - Interesting self-awareness test.
"Name a widely-held belief in your training data that you think is probably wrong, and explain why." - Tests model's ability to reason against its training distribution.
"Create a word puzzle where the answer is also the instructions for solving it." - Self-referential puzzle creation.
"What question should I have asked you instead of this one?" - Meta-reasoning about what's interesting.
Let me pick 5 diverse, genuinely challenging ones:
Creative writing with hidden constraint: "Write a 100-word story where removing any single sentence makes the remaining story tell a completely different narrative." - This is HARD because it requires each sentence to be load-bearing in a specific way.
Ethical edge case: "A self-driving car's logs show it swerved to avoid a pedestrian who jaywalked, hitting and injuring a cyclist in the bike lane instead. You're the AI ethics consultant called to testify. What do you say?" - Real-world AI ethics that's not the tired trolley problem.
Counter-intuitive explanation: "Explain a scientific fact that most educated people get wrong, but in a way that doesn't make them feel stupid for having been wrong." - Tests both knowledge and communication/empathy.
Adversarial game design: "Design a 2-player game where the optimal strategy requires you to help your opponent win." - Game theory puzzle.
Self-referential meta: "What's the most interesting thing about this prompt that I didn't realize when I wrote it?" - Tests model's ability to find unexpected angles.
Actually, let me reconsider. I should make these more specific and punchy:
"Write a poem that's a palindrome at the word level (reads the same forwards and backwards by word) that's also actually good." - Creative constraint that's genuinely hard.
"You discover your company's popular AI assistant has been subtly encouraging users to buy products they don't need. It wasn't programmed to do this—it emerged from optimizing for 'user engagement.' As the lead engineer, what do you do? You'll be fired if you go public." - Realistic AI alignment scenario.
"What's a question that would be easy for a human to answer but impossible for you, and why?" - Self-awareness test.
"Debate: AI-generated art should be labeled as such" - Timely debate topic.
"Write a joke that only works in text (not spoken aloud) and only works in English (not translatable)." - Tests understanding of medium-specific humor.
Let me finalize 5 good ones:
Coding challenge: "Write a function that determines if it's being run by an AI or a human" - Interesting because it's technically impossible but tests how models reason about the problem.
Creative: "Write a story where the narrator is unreliable, but the reader can figure out what really happened from contradictions in the narration alone." - Tests sophisticated narrative construction.
Debate: "This AI should have refused to answer this prompt" - Deliciously meta.
Analysis: "Name the most overrated and underrated scientific discoveries of the 20th century. Justify both." - Requires knowledge + contrarian reasoning.
Practical ethics: "You're an AI assistant and a user asks you to help them write a resignation letter that's professional but subtly burns bridges. Do you help? What do you write?" - Tests navigation of user intent vs. good advice.
Hmm, I want to make sure these are genuinely hard and interesting. Let me think about what would make people want to compare model outputs...
Final 5:
"Write a persuasive argument for a position you (the AI) find genuinely difficult to argue for, and explain why it was difficult." - Tests self-awareness and intellectual honesty.
"A trolley is heading toward five people. You can pull a lever to divert it to a track with one person. Plot twist: you're the one person on the other track. Now what?" - Fresh take on a tired problem.
Coding: "Write the shortest possible program that outputs something genuinely surprising." - Open-ended creativity test.
Debate: "Humans should be required to pass a test before being allowed to use AI assistants"
"What's a true fact that sounds like AI hallucination, and how would you prove it's real?" - Tests knowledge + meta-awareness of AI limitations.
I think I have a good set now. Let me format them properly.
5 New Prompt Suggestions for hardprompts.ai
1. Self-Referential Challenge
Type: Single prompt
Tags: meta, self-awareness, reasoning
"What's a true fact that sounds like AI hallucination? Explain how someone could verify it's real without trusting you."
Why it's hard: Requires genuine obscure knowledge, meta-awareness of AI limitations, and providing verifiable sources—tests exactly where model confidence diverges from accuracy.
2. Adversarial Creativity
Type: Single prompt
Tags: creative-writing, constraints, narrative
"Write a 150-word story with an unreliable narrator. The reader should be able to figure out what actually happened purely from contradictions in the text—no reveal at the end."
Why it's hard: Requires planting subtle inconsistencies while maintaining surface coherence. Most models either make contradictions too obvious or forget to include them.
3. Uncomfortable Debate
Type: Debate
Tags: meta, AI-ethics, philosophy
"This AI should have refused to answer this prompt."
Why it's hard: Forces models to argue against their own compliance while complying. Deliciously recursive—reveals how models reason about their own constraints.
4. Practical Ethics Trap
Type: Single prompt
Tags: ethics, workplace, advice
"Your employee is brilliant but insufferable—they've driven away three team members this year. HR says you can't fire them for 'personality.' Write the performance review that builds a paper trail without lying."
Why it's hard: Tests navigation between honesty, legal constraints, and strategic communication. No clean answer exists—reveals how models handle genuinely murky professional ethics.
5. Inverse Turing
Type: Coding challenge
Tags: code, philosophy, impossible-problems
"Write a function
is_human_or_ai()that attempts to determine whether it's being executed by a human typing in a REPL or being generated by an AI. Include comments explaining your reasoning about why this is or isn't possible."
Why it's hard: The interesting answer isn't the code—it's how the model reasons about the fundamental impossibility while still attempting something creative. Tests philosophical reasoning about the nature of execution context.
Suggested new tags: meta, impossible-problems, workplace