Couple Nickname: None
Dated Between: 2003 - 2012

It wasn't Demi Moore and Ashton Kutcher's gigantic age difference that made the two of them a lame couple. That fact is more creepy, especially when you consider the fact that Kutcher is only ten years older than Moore's oldest daughter, Rumer. Instead, what made these two deserve a spot on this list was actually they way their six-year marriage ended: With reports that Kutcher had cheated on Moore with a 22-year-old he met in San Diego and, on the day of his and Moore's anniversary, no less.

News of the cheating, and then Moore and Kutcher's subsequent break-up dominated the news and tabloids for ages, and it led to Kutcher getting with the sexiest woman alive, Mila Kunis. Basically, it ended well for no one except Kutcher.