Couple Nickname: None
Dated Between: 2007 - 2010

We're sure that Justin Siegel is a perfectly nice guy, but this relationship is just another case of a clearly hot girl having the ability to do so much better than the guy she's with. Emmy Rossum secretly married music executive Siegel in 2008 when she was just 22, and they kept the union so on the down-low that it wasn't even known she was married until the two broke up in 2010.

No reason was given for the split, but Rossum has since said in interviews that the divorce "wasn't the end of the world," and she "knew" that she was going to be OK. Clearly, Siegel didn't feel the same, as he requested spousal support in addition to citing irreconcilable differences in his divorce papers. The request was denied.