Couple Nickname: None
Dated Between: 2004 - 2005

Brandon Davis and Mischa Barton's relationship was weird when it was happening. The two dated between 2004 and 2005 when Mischa was still considered one of the hottest celebrities in young Hollywood, and Brandon...well, wasn't. But it was more what happened afterwards that cements their spot on this list.

Five years after their break-up, a tweet popped up on Davis's Twitter reading: "Omg. Just realized my ex turned in to 1 of the fattest people in the planet. I'm gonna start dating plus size models. Not! Mischa the Hefer" [sic].

Though Davis later claimed that he did not post the tweet and doesn't even have a Twitter account—the account had been created a week before the tweet was posted—the New York Daily News reported that the two did run into each other that night, making the whole story a bit confusing. Either way, Mischa could have done better.