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Madonna's Ex-Files: From Sean to Guy and Beyond

Wed., Oct. 15, 2008 6:54 PM PDT by Ted Casablanca

Ron Galella/Getty Images

To know where you're going with Madonna, Mr. Rodriguez, it's best to know where she has been, love-wise. With the Big M being the most recent Hollywood scheduled divorcée (officially, at least) we want to ensure we don't have another sad postsplit Jennifer Aniston sitch on our hands. So we can all educate ourselves, let's take a look at where M's gone wrong in her past 'ships and where it should've gone better.

To begin with, there were Dan Gilroy (X-BF, 1979-1980) and Steve Bray (X-BF, 1980-1982), both one-time members of the Breakfast Club. And then: