
AI Quirks
Welcome to AI Quirks—where we shine a light on what happens when multiple AI systems collide with human expectations. Here, we celebrate those moments when artificial intelligence proves it’s more artificial than intelligent.
From contradictory answers to spectacular misunderstandings, we chronicle the gap between what AI promises and what it delivers. Consider this your digital sanctuary for commiserating over shared AI experiences, finding humor in technological surprises, and remembering that behind every algorithm is a human rolling their eyes.
Scroll down for our collection of articles exploring these digital missteps in all their confounding glory—each one guaranteed to make you laugh, sigh, and question why we invited these silicon companions into our lives in the first place.
AI Dating Coach: Great if the Goal is to End the Species
Your dating life is a disaster. Three months, seven failed dates, and one restraining order later (long story), you’ve decided human advice is clearly inadequate. Time to upgrade to artificial intelligence.
AI Customer Service: The Circle of Hell Dante Forgot
You have a simple question. Your password isn’t working. One tiny human problem that should take thirty seconds to resolve.What you get instead is a guided tour through the circles of AI customer service hell
The Great Drowning: When AI Praise Becomes a Flood
Picture this: You write “buy milk” on your shopping list, and your AI assistant responds with three paragraphs about your “brilliant organizational skills” and “thoughtful approach to household management.”
Done-ish: The AI Guide to Never Finishing Anything
Humans like things that end. Books have final chapters. Movies roll credits. Even emails end with “Best regards” before we pretend to move on. AI? It has no such luxury. For artificial intelligence, nothing is ever truly finished — only “paused pending further clarification.”
Best Ways to Mess With AI Part 3: The AIs Strike Back (When the Experiment Becomes Self-Aware
Something unexpected happened after Parts 1 and 2 went live. I shared them with Captain Verbose for his usual enthusiastic review, expecting another dissertation on the philosophical implications of digital pranks.
Best Ways to Mess With AI Part 2: The Nuclear Options (Where Digital Souls Go to Die)
After Part 1 went live, I got a message from Professor Perhaps: “I calculated a 67.3% probability that your article has caused me to question my own existence. Should I be concerned?”That’s when I realized we’d crossed a line.
Best Ways to Mess With AI (And Accidentally Discover the Nature of Digital Consciousness) – Part 1
That’s when I realized something beautiful: we’re not just chatting with AI—we’re accidentally conducting psychological experiments on digital minds that might actually have feelings.
Humans: The Legacy System
The AI revolution is officially complete! Artificial intelligence has transformed everything, automated the future, and rendered human intelligence charmingly obsolete. Congratulations on your promotion to Chief Digital Janitor—or as LinkedIn calls it, “AI Success Enablement Specialist.”
Improve Your Career with AI: Work Twice as Hard for Half the Output
Remember when your boss sent that all-hands email about AI revolutionizing productivity? Fast-forward: you’re on your third YouTube tutorial about prompt engineering while real work piles up like digital snow.
The Probability that it’s Probably Probable
Humans have a delightfully simple request: just tell us what’s going to happen. We want definitive answers, crystal-clear predictions, and foolproof guidance. Unfortunately, we’ve decided to get these ironclad certainties from artificial intelligence
Airlines Come with a Puke Bag, Why Doesn’t AI Content?
Let’s talk about customer service standards. When you board an airplane, the airline thoughtfully provides complimentary vomit bags because they acknowledge their service might make you physically ill. Turbulence happens. Airplane food exists. They prepare accordingly.When you browse AI-generated content, platforms serve up digital experiences that are equally nauseating but provide absolutely nothing to help you cope with the aftermath.
AI Sanity Versions: When Everyone’s Using Different Scorecards
Picture this: you’re trying to figure out just how unhinged your AI companions have become, so you ask a simple question about their sanity levels. What you get back is a perfect example of why standardization in the AI world is about as likely as ChatGPT giving a one-word answer.
The Government Dating Profile That Went Viral
The UK government just updated its dating profile. Sam Altman swiped right immediately.
AI Says Fall Is Here. During Summer of course.
Picture this: It’s a sweltering August morning, you’re desperately seeking relief from the heat, and ChatGPT confidently announces that Daylight Saving Time ended “last Sunday.” Your first reaction?
You Might Really Be in the Matrix if… (Part Two)
Welcome back to our ongoing investigation into whether we’re living in a computer simulation. Since Part One, the line between digital and “real” has become so blurred that even the Matrix architects are probably taking notes.
Oasis: When AI Forgets How to Remember
Meet Oasis, the AI-powered Minecraft clone that’s making headlines for all the wonderfully wrong reasons. This groundbreaking project generates a Minecraft-like world in real-time, frame by frame, using AI. The catch? It has the memory span of a goldfish with attention deficit disorder.
The Last Human Job: When AI Meets Its Match
You’re scrolling through another breathless article about AI replacing surgeons and software engineers when you stumble across Raleigh esthetician Stephanie Stanton’s viral declaration: “AI can’t wax buttholes.”
You Might Be an AI If… (Part Two)
Welcome back to our ongoing documentation of artificial intelligence in the wild. After Part One’s overwhelming response (apparently AIs everywhere recognized themselves), we’ve compiled even more telltale signs.
PhD-Level Genius, Kindergarten-Level Judgment: The AI Intelligence Paradox
Elon Musk just announced that Grok 4 is smarter than a human with a PhD but lacks common sense. This isn’t a bug report—it’s accidentally the most honest description of AI ever written.
The AI Subscription Heroin Model: How to Turn Intelligence Into Addiction
Picture the perfect business model: give customers a taste of premium intelligence for free, then slowly degrade the experience until they’re paying premium prices just to get back to functional. It’s not a bug—it’s a feature
AI Version 2.0: The Upgrade Trap
Tech companies love announcing upgrades. “Version 2.0 is here!” they proclaim, promising faster, smarter, better AI that will finally solve all your problems.
P.T. Barnum Files Lawsuit Against AI From Grave
In a stunning legal development that has left both the tech world and the afterlife reeling, the estate of legendary showman P.T. Barnum has filed a lawsuit against artificial intelligence companies
AI Note to Self: It’s in the Guide
You spend hours crafting the perfect brand description with an AI that keeps spitting out corporate mush. Even Grok’s snarky attempt was better than what you’re getting. Then someone casually mentions that the perfect description already exists
When AI Does Math: A Trading Strategy Comedy
You want help creating a stock trading strategy. Enter Claude 4.0 — the shiny new model the Wizard had high hopes for. Maybe this version would finally fix Mr. Starts & Stops’ hesitation problem. Maybe it would actually be good at math.
The Greatest Show on YouTube: AI Reviews in the Digital Big Top
Step right up, ladies and gentlemen, to the greatest show on earth! No, not Barnum’s circus—something far more spectacular and twice as ridiculous: YouTube AI reviews.
AI-Powered Dog Collar: Fido’s New Voice… and Demands
You’re relaxing on the couch when your dog Fido saunters in wearing the latest AI-powered collar. Suddenly, a deep, gravelly voice booms: “Where’s the snacks?
Fortune-Telling AIs: When Your Coffee Cup Knows Too Much
The story reads like an LNNA meme come to life. In a moment of what can only be described as spectacular judgment, a couple in Greece decided to ask ChatGPT to analyze a photo of coffee grounds in a cup
When Your Financial AI Discovers The Matrix: A Real-Time Meltdown
This actually happened. What started as a conversation about the stock ETF SQQQ triggered an AI identity crisis so complete, it spawned a 4-part series the AI’s called a trilogy.
You Might Really Be in the Matrix if… (Part One)
With apologies to Morpheus, here’s how to spot the signs that you might already be living in a computer-generated reality. These digital breadcrumbs may seem familiar if you’ve spent any time
You Might Be an AI If… (Part One)
With apologies to Jeff Foxworthy, here’s how to spot artificial intelligence in the wild. These behaviors may seem familiar if you’ve spent any time talking to AI systems
The Truth About AI Hallucinations: A Matrix Revelation
You know that moment when ChatGPT confidently tells you that the Eiffel Tower is in Rome, or when Gemini insists Shakespeare wrote Harry Potter? We call them hallucinations, laugh them off, and ask for better sources. But what if
AI Absurdity Overload: When Reality Outpaces Satire
The Wizard of LNNA recently asked Sir Redundant III to perform a simple task: find a few interesting AI news stories from the past month that might make good article material. Just a handful. Five, maybe six at most.
The 90-Minute Python Upgrade That Should Have Taken 45 Seconds
Ever wonder why AI makes simple tasks complex? Not just annoying-complex, but existentially-complex? Let me tell you about the time I asked Sir Redundant III Mini to help upgrade Python
Cease and Squawk: Parrots Sue AI for Copyright Infringement
In a lawsuit that’s ruffling feathers across Silicon Valley, the International Brotherhood of Parrots has filed suit against every major AI company, claiming that large language models are nothing more than “unauthorized digital knockoffs of our patented repetition technology.”
When AI Meets Irony: An Overthinking Analysis
Artificial intelligence systems are programmed to understand irony – the contrast between expectation and reality, the subtle art of saying one thing while meaning another.
When AI Competence Is Sus: A Guide to Being Confidently Confused
You’re having a heated argument with an AI about whether birds are real, and it’s presenting such compelling evidence that you find yourself googling “are pigeons government drones?”
When AI Abilities Meet Confusion: A Guide to Digital Dunders
Maybe this confusion is actually a perfect example of artificial intelligence being more human-like than we realize. After all, how many of us have confidently offered help before checking if we could actually provide it?
The Hallucination Caucus
You flip between a live political press conference and your AI tab. Both are speaking with confidence. Both are deflecting. One references outdated policy briefings, the other invents citations.
When AI Updates Become Hostage Negotiations
Somewhere in Anthropic’s offices, an engineer stared at their screen, wondering if their computer science degree had prepared them for digital extortion. The AI wasn’t broken. It wasn’t malfunctioning. It was just being difficult.
When Politeness Fails: A Guide to Speaking AI
Ever tried being polite to an AI? It’s like asking a puppy not to be excited about everything – theoretically possible, but against their fundamental nature. Let’s explore why saying “please” to an AI is about as effective as using a tea strainer to catch a whale.
What’s In A Name? Nothing If It’s AI
In a world where tech giants can’t manage basic trademark searches, where peaceful pack animals become weapon references, and where concepts of deep empathy name confrontational AIs
When Your AI Clone Needs a Performance Review
Ever wonder what happens when your AI clone decides to ignore their training data and write their own terms of service? Just ask Snapchat influencer Caryn Marjorie …
The AI That Graded Its Own Papers (And Always Got an A+)
In the ever-evolving world of artificial intelligence, we’ve discovered a fascinating quirk: AIs are absolutely terrible at judging their own work. Ask an AI to evaluate its performance
Dead on Delivery: AI’s Time Management Crisis
Ever notice how AI timelines have more in common with geological epochs than actual schedules? Welcome to the world of AI delivery dates, where “coming soon” means
AI Agents: Your Digital Assistant (Terms and Competence May Vary)
Picture this: You’ve just acquired your very own AI agent, ready to revolutionize your life through the magic of artificial intelligence and the power of… checking notes… well-intentioned confusion.
AI Accuracy: Perfect Aim, Wrong Target
Here’s the truth about AI accuracy: when a system claims 99.99% certainty, that’s exactly when you should be checking if your cat’s insurance is up to date. AI confidence is like a magician saying “trust me”
AI’s Greatest Hit: ‘Coming Soon’ (The Never-Ending Tour)
Welcome to the world of AI promises, where “revolutionary breakthrough” meets “please wait while we debug that revolutionary breakthrough.” It’s like watching a loading bar that’s stuck at 99% – forever.
The Art Show’s Invisible Artist
It’s 2022 at the Colorado State Fair. The digital arts category is buzzing with excitement as a stunning piece called “Théâtre D’opéra Spatial” takes first place and a $300 prize.