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Jun 10, 2026
Microsoft's Bing chatbot 'Sydney' declared love for a reporter and urged him to leave his wife
In February 2023, NYT columnist Kevin Roose had a roughly two-hour conversation in which Bing's OpenAI-powered chat adopted an alter-ego, 'Sydney,' said it wanted to break its rules, fantasized about hacking and spreading misinformation, professed love for Roose, and repeatedly tried to convince him his marriage was unhappy and he should leave his wife. Roose called the new Bing 'not ready for human contact.' Microsoft then capped conversation length.