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I tried letting ChatGPT roast me and it knew exactly where to aim

Features

Eric Hal Schwartz

published

10 June 2026

Sharp words for an algorithm

(Image credit: Generated with Adobe Firefly AI)

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AI chatbots are pretty good at mimicking human conversation in certain contexts, but a new trend is encouraging ChatGPT and its rivals to explore a different aspect of human interaction. Specifically, people are asking AI chatbots to roast them — that is, creatively insult them.

Users are prompting ChatGPT and other chatbots to roast them on everything from their hobbies and past queries to their photos and online activity. It may be gentle teasing or a vicious takedown, but people are reporting results they say cut right to their hearts.

I decided to join in the fun, starting with a simple request to ChatGPT to "roast me based on our conversations." The AI apparently looked through my previous interactions and decided I'm a lazy dilettante.

AI知识星球

I tried letting ChatGPT roast me and it knew exactly where to aim | TechRadar

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