40. Taylor Swift and John Mayer
Couple Nickname: None
Dated Between: 2010
We get it, every girl wants a bad boy that they can be the one to "change," because, of course, popular culture dictates that deep down inside every player, there's a sensitive soul just waiting to be found and nurtured. That said, we're really not sure what Taylor Swift was thinking when she got with John Mayer.
Sure, he's the guy who wrote about an ex-girlfriend's body being a "wonderland," but he's also the same guy who talked about something called a "hood pass" and announced to the world that Jessica Simpson was like "sexual napalm" to him.
A leopard can't change its spots, and even Taylor Swift should've known that her cutesy laugh can't change John Mayer's predisposition to being a hilarious jerk sometimes.