#5. Justin Timberlake and Cameron Diaz
During their entire, nearly four-year relationship, the former 'N Sync-er and star of There's Something About Mary endured rumors that they were either breaking up or getting engaged. In January, the pair finally announced the former with little fanfare. In fact, the most dramatic moment in this split was an awkward and much-photographed meeting on the red carpet at the Shrek the Third premiere four months post-breakup. They kissed and lived happily ever after without each other.
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