Couple Nickname: None
Dated Between: 2008

Infidelity from one party in any relationship is always enough to get stamped with the title of 'lame,' which makes the affair that took place between The Yankees' Alex Rodriguez and superstar Madonna so much worse.

Both A-Rod and Madonna were married at the time—him to Cynthia Scurtis for six years and Madonna to Guy Ritchie for seven and a half—and Cynthia's divorce attorney reportedly told TMZ that A-Rod's affair with Madonna was "an affair of the heart" as opposed to a physical relationship. Ouch.

Even worse, both A-Rod and Madonna have kids with their spouses, so not only did their relationship wreck marriages, but it broke up families as well. Classy doesn't even begin to cover this one.