1. Kim Kardashian & Reggie Bush
Kim Kardashian started dating Reggie Bush in 2007, but they split in 2009 due to hectic work schedules. Kardashian reunited with the New Orleans Saints player in the fall of 2010 before calling it quits again -- after the team's Super Bowl win. Dating rumors swirled about them yet again in early 2012 when they were seen making nice at lunch in L.A. just months after the reality star divorced that guy who plays basketball.