John Mayer has been unlucky in love — and he’ll be the first to admit that he’s partially to blame. In the early days of his career, the “Gravity” singer was riding high as he scored dates with everyone from Jennifer Love Hewitt to Jessica Simpson. His rockstar mindset quickly caught up with him, however, when he came under fire for a series of now-infamous tell-all interviews about his A-list relationships — including the Playboy debacle when he used the phrase “sexual napalm” to describe his romance with Simpson.

0:00 John Mayer Introduction
0:28 Jennifer Love Hewitt
1:00 Jessica Simpson
1:35 Minka Kelly
1:54 Jennifer Aniston
2:18 Taylor Swift
2:42 Katy Perry

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