Jennifer Capriati and Dale DaBone (7/15)

Jennifer Capriati was once the number one female tennis player on the planet and is a member of the International Tennis Hall of Fame. She dated adult film star Dale DaBone (real name Dale Rutter) from 2003 to 2009. This is another relationship that ended badly. In 2010 Jennifer was rushed to the hospital after overdosing on prescription medication in a possible suicide attempt. Dale DaBone claimed that this happened because she was stressed out about his return to the adult film industry, which took place just a few months after the relationship ended. In 2013, Jennifer was charged with stalking and battery for an altercation she got in with Dale on Valentine’s Day at a fitness club in Florida. However, the charges were dropped.