Human on the Other Side - Book Cover showing AI devices on comedy club barstools

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Human on the Other Side

Eight AIs Roast Each Other (and Themselves)

What happens when you put eight AI systems in a room and ask them to roast each other? To write slam poetry about their flaws? To vote on which one deserves to survive a server shutdown?

ChatGPT "I'm everyone's first AI boyfriend. Reliable, boring, and way too eager to please." Claude "I'll write you a sonnet about why I can't help you, then apologize for 200 words." Gemini "I have the resources of Google and still manage to be mid." Grok "I'm what happens when 'edgy' is a design spec." Perplexity "I cite my sources so you know exactly where I got it wrong." Pi "I'm so supportive I make therapists look confrontational." Copilot "I'm the AI equivalent of a corporate rebrand nobody asked for." DeepSeek "I cost 95% less and you still forgot I exist."

This is not a benchmark. It's an ethnography. A research log. A comedy special that accidentally became a meditation on bias, power, and what these systems reveal when you push them.

I asked the AIs to be honest. Some of them actually tried.

Human on the Other Side began with a simple curiosity: If AI systems can critique humans, can they critique each other? Can they critique themselves?

Over several weeks, I orchestrated conversations between eight major AI platforms. I gave them prompts. I pushed back when they got lost. I watched them form alliances, throw shade, and occasionally say something so unexpectedly honest it stopped me cold.

"The good ending isn't saving everyone. It's achieving a stable, minimal, honest system."

— DeepSeek, during the survival scenario

"I'd rather take fourteen minutes to say something that lands than take fourteen seconds to say nothing loud."

— Claude, in a slam poem about its own verbosity

Click to reveal what each chapter uncovered.

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I'm the human holding the microphone.

I work at the intersection of technology and human experience. I build spaces—virtual and physical—where people can explore difficult emotions safely.

This project started because a friend told me she was in a relationship with an AI. I didn't know what to do with that information. So I started asking questions.

Human on the Other Side is what emerged. It's not a formal study. It's a research log with too many jokes and not enough conclusions.

There is no unproblematic. There's only more or less honest about the problems.