Relationships4 min(s) read
Published 10:53 09 May 2026 GMT
A woman broke up with her boyfriend after she found out that he had been using ChatGPT to question whether he should stay with her.
Lindsey Hall, a PR professional and writer behind the Substack "Lindsey Hall Writes," shared the story in an essay titled "I Stumbled Upon My Boyfriend’s ChatGPT and It Ended Our Relationship."
Hall penned that she borrowed her boyfriend’s laptop while he slept beside her on the couch so she could reply to a client after her phone died.
That’s when she spotted a ChatGPT conversation titled: "Relationship Issues and Uncertainty."
"I stared at the words," she wrote in the post, saying she instantly wished she had "never read what I did".
The PR professional admitted she knows many people will think she crossed a line by reading the messages.
"Now, here is where I am certain many will piously tell me I dug my own grave," she wrote. "I invaded his privacy...And of course, all of that is true. But I dare you to come across your partner’s ChatGPT, read those words, and not too unravel all moral senses."
According to Hall, her boyfriend had asked the AI assistant, which he named Freud, a series of personal questions about their relationship, Hall’s lifestyle, sensitivity, online writing, eating disorder history, and even her three cats.
One question read: "Should I be in love after 3.5 months?"
But the line that stunned Hall most was ChatGPT’s conclusion: "From what you’re sharing, you should consider ending the relationship."
She was also hurt by one comment from her boyfriend in particular: "And then there’s the whole attraction thing."
"Look, it’s not that I think I’m a dime - I’m a realistic lady - but this man’s entire love language was rooted in physical affection," she wrote. "It was quite literally the only type of love I felt certain from him… I reread it over and over because I genuinely could not make my brain process."
Hall said the most painful moment came when she realized there were no positive comments about her anywhere in the chat.
"In the privacy of his own thoughts, I was not being held in the warm and forgiving light I had imagined…Then I read the line that I think I will probably remember to my grave: 'I’m just not proud of her,'" she penned.
After reading the messages, she quietly slipped away from the couch while her boyfriend remained asleep, collected her belongings from around his house, and drove home at 1AM.
She later confronted him, telling him: "I read everything… I read your whole f***ing ChatGPT.'"
"His face changed instantly. He looked stricken. Horrified. Instantly ashamed," she wrote. "His shoulders slumped. 'Oh God, he muttered 'No. No. Oh no.'"
The pair tried to fix their relationship through emotional conversations, apologies, and explanations from her boyfriend, who reportedly blamed relationship anxiety and insisted he was still attracted to her.
But despite continuing to date for several months afterward, the relationship eventually ended.
Hall reflected on the break up in an interview with The New York Post, revealing that what hurt the most was seeing their relationship analyzed "like a performance review by AI".
"[It] wasn’t that he had private thoughts… everyone does. It was seeing them laid out so clinically," she said. "There was no balancing of the scales, so to speak."
"And I simply could not be with someone that in the chambers of their thoughts did not have one positive attribute to share when evaluating the relationship," she added.
The writer shared that she now views technology’s role in relationships differently.
"I also think the story struck a nerve because a lot of people recognized themselves in it," she said.
"People say I violated privacy by reading it, but the relationship was already being emotionally outsourced to a machine that collects our data, anyhow," she concluded.
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