John Mayer Dating History: Jessica Simpson, Jen Aniston, more

John Mayer has been unlucky in love – and he’ll be the first to admit he’s partly to blame.

In the early days of his career, the “Gravity” singer was riding high as he scored dates with everyone out Jennifer LoveHewitt Unpleasant Jessica Simpson. His rockstar mentality quickly caught up with him, however, as 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.

Initially, the Grammy winner was unapologetic: “I want girls to like me. I want to make music and be considered attractive,” he shared The New York Times in a March 2017 profile — but as time went on, he began to realize that he “started to invent my own grenade,” he told the Times.

As 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 wrote a handful of songs 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 Space for squares singer has not had a serious romance since his breakup with Perry in 2014, he wants to tie the knot eventually. “Of course I want to get married,” he shared on the podcast “Call Her Daddy” at the end of 2022.

Keep scrolling to see Mayer’s A-list romances over the years: