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The lawsuit stems from an allegation from a commenter on one of the site's stories, claiming she contracted chlamydia from Bilzerian.
According to TMZ, the comment in question reads, "I ended up getting super drunk and sleeping with Dan. I got tested two weeks later and lucky me I found out he gave me chlamydia." Bilzerian claims he is STD-free, and therefore the statement is defamatory.
Step one in proving defamation for Bilzerian is to prove he is clean -- a true statement, no matter how injurious, cannot be defamation. While we have not seen the lawsuit itself, one would imagine that Exhibit A to Bilzerian's complaint would be his STD test.
Even if Bilzerian is clean, TheDirty.com and founder Nik Richie (who is also named in the suit and has been feuding with Bilzerian) may have a defense to any defamation claim. First, news publications (and I use that term as loosely as possible here) are generally given more deference when it comes to potentially defamatory statements that could be in the public interest. Especially, as TMZ points out, websites that don't edit their comments section.
Although The Dirty could claim the statement isn't theirs, they did "publish" it, and, according to Bilzerian's lawsuit, the website also posted pictures of him with several women next to the comment.
Second, Bilzerian is a public figure (just ask his Instagram account), therefore he can't recover unless Richie and The Dirty knew the statement was false or acted in reckless disregard of the statement's truth or falsity. This must be the case due to the "actual malice" standard, which applies to public figures in defamation cases.
Bilzerian is no stranger to litigation, especially for tossing things around.