30. Charlie Sheen and Bree Olson
Couple Nickname: None
Dated Between: 2011
When Charlie Sheen had his breakdown in 2011 that resulted in his divorce from wife Brooke Mueller and the loss of his longtime Two and a Half Men gig, he claimed to be running on "Tiger's Blood" and shacking up with girlfriends he called his "goddesses." One of them was adult film star Bree Olson, who more or less supported his mental breakdown and his subsequent decisions in the media.
During her initial four-day stint with him, she "retired" from the adult film industry because he wanted her to, though she personally "didn't believe in it." A few days later, however, Sheen was tweeting that Olson had left the house, and that "applications are now being accepted." Two hours later, Sheen updated that Olson had returned, and the two were together for another month before calling it quits.
One of Sheen's biggest problems during that time period was the fact that he was surrounding himself with total yes-men. And from the way it looks, Olson was definitely one of them.