A 25-year-old former Goldman Sachs analyst in Florida reportedly told ChatGPT about plans to sexually assault and kill his ex-girlfriend. The conversations later became part of an FBI investigation after OpenAI alerted federal authorities. As reported by the South Florida Sun Sentinel, Darren Zhou, who was arrested in May, pleaded guilty to three charges on August 13. He avoided prison under a negotiated agreement and was sentenced to eight years of probation with strict conditions, including electronic monitoring and a ban on contacting his former girlfriend.The case has drawn attention to how conversations with AI chatbots can become part of a criminal investigation when messages indicate a possible threat to someone’s safety.
From breakup conversations to threats against his ex
As reported by the South Florida Sun Sentinel, Zhou began using ChatGPT in March 2026, after his six-month relationship with his former girlfriend ended. His early conversations reportedly focused on the breakup, his former girlfriend’s interests, places she visited, jealousy and his desire to reconcile. Investigators later said the messages became increasingly specific and included discussions of violence.Zhou allegedly told the chatbot he wanted to kill his ex-girlfriend if she refused to take him back. His alleged threats later expanded to include sexual assault, hostage-taking and violence against members of her family. The investigation reportedly covered around two months of his ChatGPT conversations.
What investigators found in the chat history
The messages reviewed by investigators were described as more than expressions of anger or distress. According to South Florida Sun Sentinel, they contained repeated discussions of possible violence and plans involving his former girlfriend. Zhou allegedly discussed waiting for her at a gym with flowers and asking her to reconcile. Investigators said he described a plan to use a gun if she rejected him. Zhou discussed forcing his former girlfriend to go to his home, sexually assaulting her and holding her captive.Investigators reportedly found messages in which he claimed to have access to firearms. India Today said the chat history included references to an AR-15-style rifle, a Glock handgun and a 12-gauge shotgun. These details were reported from court records and investigative documents. The messages and allegations formed part of the criminal case against Zhou.
How OpenAI alerted the FBI
According to the reports, the chats contained repeated discussions of possible violence and plans involving his former girlfriend.
The case began with OpenAI detecting the threatening conversations, according to the reports. FBI received information from OpenAI and provided Palm Beach County investigators with around two months of Zhou’s chat history. The FBI reportedly contacted local authorities six days before his arrest. The Palm Beach County Sheriff’s Office then conducted a welfare check on Zhou’s former girlfriend, who was 21 at the time.She told investigators that she had ended the relationship because of Zhou’s erratic, jealous and controlling behaviour. She reportedly chose to break up over the phone because she was afraid of his reaction. Investigators also said Zhou continued contacting her after the breakup through phone calls, text messages and social media. When she blocked him, he allegedly used numbers generated through different apps to continue contacting her. The woman provided screenshots of the alleged communications, according to the report.
Arrest, charges and eight-year probation sentence
As reported by the South Florida Sun Sentinel, Zhou was arrested in May 2026 and spent two days in the Palm Beach County jail before posting $100,000 bail. He faced three charges: Aggravated stalking, Written threats to kill and Illegal use of a cellphone. On August 13, Zhou pleaded guilty to all three charges as part of a negotiated agreement with prosecutors. The agreement allowed him to avoid prison and a felony conviction. Circuit Judge Scott Suskauer withheld adjudication and sentenced Zhou to eight years of probation.
Conditions of his sentence
The probation order includes several restrictions, according to the reports: Electronic monitoring through an ankle monitor for the first two years. Completion of a batterer intervention programme. A mental health evaluation. No drugs or alcohol. No possession of guns. No contact with his former girlfriend. The judge accepted the agreement partly because Zhou’s former girlfriend had agreed to it.
What the case says about private AI conversations
The investigation has also raised questions about how AI companies handle messages involving potential real-world violence. ChatGPT is used for everyday tasks, personal conversations and advice. But in this case, investigators said the chatbot conversations contained detailed threats against a specific person.The Florida case comes amid wider attention on the use of AI tools in criminal investigations. Authorities in a separate Bengaluru triple-murder investigation said the accused had used Google’s Gemini chatbot while planning the killings. Investigators reportedly sought access to the AI chat history as part of that probe.
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