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Legal fail: Don’t use AI to sue Facebook users for calling you a bad date

May 19, 2026 Development Source: Ars Technica

Legal fail: Don’t use AI to sue Facebook users for calling you a bad date

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In an opinion Friday, David Hamilton, a senior circuit judge for the US Court of Appeals for the Seventh Circuit, wrote that the three-judge panel agreed that “this is a relatively rare appeal in which sanctions appear to be appropriate.” Not only was the appeal deemed “frivolous” for failing to advance D’Ambrosio’s arguments, but it was also littered with “mistakes and fictitious quotations” that “bear the hallmarks of the misuse of generative artificial intelligence,” Hamilton said. “Briefs and other court submissions that include fictitious quotations—inaccuracies discoverable with elementary professional care—are unacceptable,” Hamilton wrote. MarcTrent.AI did not immediately respond to Ars’ request for comment on whether the firm plans to fight the potential sanctions. The firm has until June 16 to request a hearing or file statements on whether sanctions are warranted. D’Ambrosio’s legal fight started when a woman whom he briefly dated, Abbigail Rajala, blocked his number, and he persisted in sending a menacing text by using an alternate number. Additionally, he tried to blame Rajala for another woman’s reply on the thread, which linked to a mug shot of a convicted rapist. Despite the mug shot link displaying another man’s name and photo, D’Ambrosio claimed he had been defamed and had “suffered emotional distress, emotional loss, loss of professional opportunities, and damage to his reputation and relationships.” His goal, Hamilton’s opinion noted, was to sue “anyone remotely associated with those posts for all possible, imaginable claims, including the woman who dated him and her parents, women commenting on posts, the operators of the Facebook group, and Facebook itself.” In his blog, Trent acknowledged that these Facebook groups “were ostensibly created to help women navigate dating safely,” but he claimed that some women abuse the groups to instead trigger harassment campaigns by accusing innocent men of spreading sexually transmitted infections or forcing women to having abortions. After pushing the “frivolous” appeal, D’Ambrosio’s lawyers now face potential sanctions on three fronts: for misleading the court over the authenticity of the screenshot, using AI to introduce fake and deceptive citations, and filing a frivolous appeal. Sanctions could include fines covering the costs for the Rajalas to fight the appeal, as well as possible fines for Trent and another attorney at his firm, Aaron Walner. “In short, D’Ambrosio and his attorneys failed to advance any conceivable reason for this court to reverse the dismissal of any of his claims against any of the Rajalas,” the appeals court panel ruled. Regarding the fake citations, the panel said that it focused its analysis on a section of a court filing that “seemed to have the highest density of them,” while emphasizing that it was a “serious” problem when lawyers submitted such “sloppy” work. On top of misquoting statutes and misrepresenting legal standards, the filing also made broad claims about what constitutes doxing without citing a single case to support their stance. In a footnote, the panel appeared particularly frustrated that Walner not only didn’t seem to review fake citations included in the filing, but he also neglected to sign the filing, which is supposed to serve as a lawyer’s stamp certifying his review. In some cases, lawyers have offered some pretty wild excuses for relying too much on AI, but it’s increasingly rare for the court to forgive and forget, so sometimes ‘fessing up and sincerely apologizing can help to lower fines. However, whether D’Ambrosio’s lawyers admit to using AI or not, the panel still could order sanctions. “Submitting fictitious quotations to a court, regardless of how they are generated, is obviously inconsistent with the standards of conduct this court expects from attorneys practicing in this court,” Hamilton wrote.