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Coincidentally, Damon and Affleck's respective girlfriends, Ryder and Paltrow, also lived together in LA in the '90s. They cut ties in 1998 when Paltrow reportedly stumbled upon the script for "Shakespeare in Love" lying around the house; Paltrow is said to have asked to audition for the role, and as we all know, she landed it and went on to win an Oscar.
Though Paltrow has denied swiping the role from Ryder, things came to a head again in 2009 after she launched her now-famous website, Goop. In an early article, she addresses a former friend that many speculate to be Ryder, saying, "Back in the day, I had a 'frenemy' who, as it turned out, was pretty hellbent on taking me down." She went on to write: "I restrained myself from fighting back. I tried to take the high road. But one day I heard that something unfortunate and humiliating had happened to this person. And my reaction was deep relief and happiness."