Legal fail: Don’t use AI to sue Facebook users for calling you a bad date - Ars Technica
Overview
Legal fail: Don’t use AI to sue Facebook users for calling you a bad datevar abtest_2155061 = new ABTest(2155061, 'click');
Fake citations dashed a dude’s “Are We Dating the Same Guy” revenge lawsuit.
Details
An attempt to pressure Meta into removing a critical post from a Chicago Facebook group called “Are We Dating the Same Guy” may end in sanctions for lawyers whose takedown arguments appeared to rely on fake AI citations to support doxing claims.
The case had already been dismissed with prejudice by a district court, which ruled there was no way to amend the complaint to possibly save it. But Nikko D’Ambrosio—who accused more than two dozen women of defaming him and blamed Meta for supposedly boosting the post to profit off its “entertainment value”—appealed anyway.
Perhaps he felt confident despite his likely tough odds because he was relying on Marc Trent. AI, a law firm that claims to use AI to “uncover legal opportunities traditional firms miss” and “increase legal success rates by 35 percent through predictive modeling.”
In a 2025 blog discussing the case, founder Marc Trent confirmed that the firm had “utilized our tech team to draft” the initial complaint. He boasted that the “evolved” firm uses “everything related to AI now,” suggesting that “even Meta can’t beat us” and claiming that a win would make Facebook safer for everyone.
Laying out the case, Trent said that he assumed that Meta “would quickly distance itself by removing the post.” But when Meta didn’t, he figured that overcoming Section 230 claims would be his biggest hurdle in the fight. However, he insisted that “his firm’s technological capabilities” would level the playing field, making it possible to beat Meta’s well-resourced legal teams who are deeply schooled at defending against Section 230 claims.
However, during the appeal, judges agreed that the case was so weak that Section 230 didn’t even factor in. And the firm’s seeming reliance on AI to “execute” arguments “with precision” apparently did not help matters at all.
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.
Marc Trent. 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.
Screenshot of text D’Ambrosio wanted removed from Facebook.
Rajala posted a screenshot of the text in a thread where more than two dozen women started sharing photos of D’Ambrosio and criticizing him. Importantly, Rajala did not urge any call to action, like contacting his family or employer, or reveal his phone number or any other identifying information.
Since the post was popular, it stuck to the top of the Facebook group’s feed, frustrating D’Ambrosio, who tried to claim that Meta was disregarding his safety by promoting the post.
None of his arguments won out, but D’Ambrosio was hoping the court would agree that Rajala—and her parents, since she posted using their home Internet connection—had doxed him. He also tried to accuse Meta of profiting off his likeness by running ads alongside the post.
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.
“They’re facilitating having people contact their bosses, their employers, to take the harm even further,” Trent alleged.
But importantly, D’Ambrosio failed to allege any concrete harm caused by the post, and there is no evidence that the post led to improper contacts in the real world.
He also never argued that anything that the women said about him was false. Extremely late in the game, his lawyers tried to save his case by arguing that it was possible that the screenshot Rajala shared was doctored. But the panel rejected that argument since D’Ambrosio had ample opportunity to dispute the text’s authenticity earlier in the litigation, and never did it before oral arguments during the appeal.
An Internet law expert monitoring the case, Eric Goldman, explained that D’Ambrosio’s case is similar to other lawsuits where men have tried and failed to get critical posts removed from “Spill the Tea”-branded Facebook groups like the Chicago-based “Are We Dating the Same Guy” group. But repeatedly these men fail, largely because posts like Rajala’s are considered opinions protected by the First Amendment and defamation laws in states like Illinois.
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.
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Key Takeaways
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Legal fail: Don’t use AI to sue Facebook users for calling you a bad datevar abtest_2155061 = new ABTest(2155061, 'click');
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Fake citations dashed a dude’s “Are We Dating the Same Guy” revenge lawsuit
-
An attempt to pressure Meta into removing a critical post from a Chicago Facebook group called “Are We Dating the Same Guy” may end in sanctions for lawyers whose takedown arguments appeared to rely on fake AI citations to support doxing claims
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The case had already been dismissed with prejudice by a district court, which ruled there was no way to amend the complaint to possibly save it
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Perhaps he felt confident despite his likely tough odds because he was relying on Marc Trent
