Man who sued women for trash-talking him on Facebook sentenced for tax fraud


Nikko D'Ambrosio, left. (Photos from court documents)

Nikko D’Ambrosio, left. (Photos from court documents)

A Chicago man who filed a defamation lawsuit against dozens of women he accused of trash-talking him in a “Are We Dating The Same Guy” Facebook chat group has been sentenced to prison for tax fraud.

Nikko D’Ambrosio, 32, learned his fate this week. He was convicted in January of two counts of false statements on his tax forms for 2020 and 2021. He claimed expenses and deductions for charitable donations to a church that had no record of him being a registered parishioner. He also claimed meals and mileage for his work as an installer of electronic sweepstakes kiosks at gas stations and later lying to an IRS agent when he said his tax forms were correct and he had “wined and dined” business owners in connection with his work, court documents said.

“The miles you said you drove would have allowed you to drive to the moon and back,” U.S. District Judge Thomas Durkin told him before handing down the one-year sentence, the Chicago Tribune’s Jason Meisner reported. “And you lied badly. You doubled down.”

D’Ambrosio apologized.

“I’ve established myself as a good family man,” he said, according to the Tribune. “I do go to church. I’m loyal to my faith.”

One of D’Ambrosio’s attorneys said the case wasn’t about greed, “It’s about stupidity.”

“I don’t mean this to disparage Nikko in any way, but as you can see from his educational records, he is not the most sophisticated human being,” Christopher Grohman told the jury, the Tribune reported. “Somebody with his skill set is not doing his own taxes, and nor should he be, frankly. You go to a professional. And the professional he relied upon was his cousin.”

Prosecutors called that hogwash.

“This [isn’t] a whodunit without the mystery,” Assistant U.S. Attorney Richard Rothblatt said. “This isn’t ‘The Usual Suspects’ with Keyser Soze and a dropped mug … The defendant had 119,000 reasons to lie.”

D’Ambrosio filed a lawsuit in January against Facebook and individuals who refused to remove what he said was defamatory information on social media.

The lawsuit alleged that 50 women made false and defamatory statements about him in an online group that claims to have more than 3 million registered users who “discuss and disparage men in their local communities with which they have had allegedly unsatisfactory dating experiences.”

The group, “Are We Dating the Same Guy?” is a collection of “Red Flag Awareness groups all across the country where women can empower each other and keep each other safe from toxic men,” court documents said.

It is a place where women can anonymously “dox, defame, and attack the moral character of men they’ve met online,” court documents said.

One of the defendants, who met D’Ambrosio at a cultural event in Chicago in 2023, had sex with him on the night they met and spent time together a handful of times later, which were described as unremarkable, the lawsuit said.

The woman was accused of publishing “provably false and defamatory statements” about D’Ambrosio and a photo of him on the Chicago Facebook group page. The post was taken down and republished anonymously, court documents said.

Others described him as “clingy” and a “ghoster,” according to the lawsuit.

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