1. The Lei of the Land

Date: 7/9/2011 (Deleted)
Once Jose Canseco met Leila Shennib in 2009 at the Playboy Mansion, the two fell in love quickly, much to the disapproval of the model's family and friends. When the pair broke up after two years together, Canseco took to Twitter to discuss personal matters and even posted Leila's phone number. Stay classy, Jose. Stay classy.