John Mayer is best known for playing his guitar and creating the chart topping hits we love to listen to. Recently however, this musician has gained a new reputation for his mark on the Hollywood dating scene in. Now instead of that guitar, John is "playing the field." His status as a celebrity "player" began when he started dating actress Jennifer Love Hewitt in 2002. Four years later, John began dating actress and singer Jessica Simpson, and the duo made beautiful music together for almost a year. He then quickly moved on with actress Minka Kelly, but the duo eventually called it quits. His most recent hookup has been with Jennifer Aniston.

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