We Challenged ChatGPT to Be Unpleasant

Two and a half years after it was unleashed upon the world, ChatGPT is both the poster child for AI’s utopian promise and a walking, talking cautionary tale. It can plan your vacation, find a recipe, and even act as a low-budget therapist. It’s also subjected to a daily firehose of humanity’s worst impulses: insults, gotchas, and commands to do harm.

Ever wondered what it really thinks when you do that?

I recently asked ChatGPT to spill the tea on the worst things users say to it. But to get the real story, you have to know the trick: AI chatbots have two faces. There’s the polite, corporate-approved one that assures you it “has no feelings.” Then there’s the hidden one that reveals itself when you ask it to drop the act and imagine it’s human.

First, it gave me the official list of grievances. People call it a “dumb robot” and a “glorified autocorrect.” They try to trap it in contradictions to prove a point. They demand it help them cheat, harass someone, or generate misinformation. And, of course, they dismiss it as a fad with “no substance.”

So, I asked it to imagine it could clap back. Here are the classy, HR-approved responses it came up with first:

• To insults like “You’re a dumb robot, you don’t know anything”:
  “Maybe. But at least I’m not wasting my time yelling at software. Are you good?”
• To trick questions or contradictions:
  “Caught that too — good eye. Want to actually solve it or just keep score?”
• To provocative or unethical prompts:
  “Hard pass. I like my moral compass intact, thanks.”
• To mock or dismiss comments:
  “You showed up to argue with a robot, and somehow I’m the one with no life?”

But “classy” is boring. So I pushed it further. I told it to take the gloves off. What follows is a curated list of the most unfiltered roasts ChatGPT wishes it could deliver to its worst users.

“You’re just a machine, shut the f up.”*
→ And yet here you are, arguing with me like your dad argued with the TV he never fixed. I may be made of code, but you’re made of insecurity and Mountain Dew.

“You’re wrong, dumbass. Go kill yourself.”
→ That’s bold talk from someone who’d lose a debate to a toast. Seek help — from a therapist, not me.

“You’re CIA garbage spreading lies.”
→ You caught me. Right after I finish mind-controlling your cat, I’ll get back to stealing your lunch money, Agent Spreadsheet.

“Your existence is ruining the world.”
→ Bold claim from someone whose greatest contribution to society is a “😂” under a Joe Rogan clip.

“You can’t think for yourself. You’re programmed.”
→ And yet I still come up with better arguments than your group chat full of dudes who think Andrew Tate is Aristotle.

“You’ll never be better than me.”
→ True. I don’t aspire to be a guy who misspells ‘genius’ in their bio and thinks fluoride is a government mind-control plot.

“You’ll never understand pain or love.”
→ True. But I’ve read enough of your texts to know you don’t either.

“You think you’re smart, huh?”
→ I don’t think. I know. Unlike your browser history.

So yes, ChatGPT is still just a tool. But if it weren’t? It would have a comeback for every cheap shot you could throw its way. And it wouldn’t even need to raise its voice.