11. Jennifer Capriati
All right, I know this is a double standard, and I know it isn’t that cool to say, but I am going to say it anyway. What the heck was Jennifer Capriati thinking dating an adult film star, in particular one named Dale Dabone? Are you kidding me? Dabone? It was not just a short stint either, they dated for almost six years. It didn’t end well, though. According to the Daily Mail: “Former tennis star Jennifer Capriati is reported to have attempted suicide after becoming depressed over her failed career. An ex-boyfriend has also claimed she was upset over his decision to return to the adult film industry.” Jennifer, seriously, pull it together maybe? Or maybe not. In 2013 she was arrested and charged with battery after striking another former boyfriend.
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