John Mayer’s Dating History: Jessica Simpson, Jennifer Aniston, Katy Perry and More

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.

At first, the Grammy winner was unapologetic — “I want girls to like me. I want to make music and be thought of as attractive,” he told The New York Times in a March 2017 profile — but as time passed, he began to realize that he had “started to invent my own grenade,” he told the Times.

Since his romance with Simpson fizzled, Mayer subsequently dated Jennifer Aniston, Taylor Swift and Katy Perry, romances that made headlines — and songs. Fans have long theorized that Swift has written a handful of tracks about Mayer, including Speak Now's "Dear John," Midnights' "Would've, Could've, Should've" and more, while Mayer's "Paper Doll" is rumored to be about the "Anti-Hero" artist. Mayer also admitted to writing music about Perry.

While the Room for Squares singer hasn't been in a serious romance since his 2014 split from Perry, he ultimately wants to tie the knot. “Of course I want to get married,” he shared on the "Call Her Daddy" podcast in late 2022.

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Keep scrolling to see Mayer's A-list romances throughout the years: