7. Jennifer Aniston
This was one of the famous hookups of John Mayer that seemed to have legs, at least for a while. John and Jen were definitely more than just “Friends“, and actually had a public long term relationship (at least by Hollywood standards). The two began dating in February 2008, and after briefly breaking up, they got back together until they split for good in March 2009. They were fixtures on the red carpet together for a while there, but then John’s excessive Twitter habit started bothering Jen so she moved on.
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