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After some on-and-off dating for about a year, including an impromptu press conference from Mayer about their first breakup, Aniston and Mayer finally called it quits on respectable terms.“I ended a relationship to be alone because I don’t want to waste somebody’s time if something’s not right,” he told reporters outside of his NYC gym in the summer of 2008.Months later, he’d show up at the 2009 Oscars ceremony on Aniston’s arm.

Before he dated Swift, Mayer was walking red carpets with Jennifer Aniston from 2008 to 2009.There was a rumor that Mayer wrote his song, “Your Body is a Wonderland,” about Hewitt.The actress, having heard the rumor, responded in a comical way. My body is more like a pawn shop,” she told Entertainment Weekly.In 2002, Hewitt was still in blockbuster films and making her appearances, which was great exposure for the rising artist on her arm.Unfortunately, this first celebrity relationship of Mayer’s didn’t last too long, and apparently they didn’t even have sex.