'Are We Dating the Same Guy' Guy Imprisoned for Tax Fraud

After suing 27 women and multiple platforms because people he'd dated warned others not to date him, he filed a class action lawsuit against them. Now, he's headed to federal prison.
'Are We Dating the Same Guy' Guy Imprisoned for Tax Fraud
Nikko D'Ambrosio. Screenshots via complaint

A man who sued more than two dozen women for calling him “clingy” and “psycho” was just sentenced to a year in federal prison for tax fraud and generating mob-connected earnings from gambling machines. During his trial, his lawyers defended him by calling their client too stupid to be held accountable. 

In January, 32-year-old Nikko D’Ambrosio sued 27 women, one man, 20 different parts of the Facebook corporation, Meta, Patreon, GoFundMe, and the website, claiming that he incurred damages after members of the Chicago “Are We Dating the Same Guy” Facebook group called him “clingy” and “psycho.”  

The judge for that case dismissed the complaint because the court did not have subject matter jurisdiction, but D’Ambrosio immediately refiled a class action lawsuit. D'Ambrosio's lawyers at Trent Law Firm were seeking others in Illinois who would come forward with claims that they’d been doxed, defamed, or had their photos posted in “Are We Dating The Same Guy” groups. “This group is a place for women to protect, support, and empower other women,” the Chicago group, and other official AWDTSG groups’ descriptions say. There are AWDTSG groups in many major cities around the U.S. 

Man Who Sued ‘Are We Dating the Same Guy?’ Groups Files Class Action Lawsuit
Nikko D’Ambrosio of Illinois had his first case dismissed, and refiled as a class action that seeks other guys who feel harmed by “red flags or tea?” dating groups.

Women posted photos from D’Ambrosio’s social media, and in his complaint he claimed that one commenter wrote, “He’s been posted here before. The poster said he sent her a slew of texts calling her names because she didn’t want to spend the night with him.” Another wrote, according to screenshots in his complaint: “Flaunted money very awkwardly and kept talking about how I don’t want to see his bad side, especially when he was on business calls.” 

Sign up for free access to this post

Free members get access to posts like this one along with an email round-up of our week's stories.