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

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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 rock-star 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. In January 2010, Mayer told Rolling Stone that his ideal woman had to have “a beautiful vagina” that he “could pitch a tent on and just camp out on for, like, a weekend.” Just weeks later, he raised eyebrows again when he used the phrase “sexual napalm” to describe his romance with Simpson, telling Playboy, “That girl is like crack cocaine to me. … Did you ever say, ‘I want to quit my life and just f--kin’ snort you? If you charged me $10,000 to f--k you, I would start selling all my s--t just to keep f--king you.’” At first, the Grammy winner was unapologetic. “I’m a young guy. I like girls. 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. However, as time passed — and Mayer’s subsequent relationships with Jennifer Aniston, Taylor Swift and Katy Perry also failed — he began to realize that he had “started to invent my own grenade,” as he told the Times. “What has to happen for a guy to believe that he’s totally well-adjusted and be that far out of touch?” he wondered, joking that he was “old enough to look back” on life and pinpoint his “downfall.” While the “New Light” crooner has not publicly dated anyone since his romance with Perry ended in February 2014, he has not shied away from talking about his love life. He revealed in the Times interview that he was on an exclusive dating app (“It’s just a lot of chatter”). And when an Instagram user asked Mayer how he was “still single” during a July 2019 livestream, he had a hilarious response: “Google me.” Scroll down to revisit Mayer’s dating history!

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Jennifer Love Hewitt

The musician and the I Know What You Did Last Summer actress dated in 2002, and he reportedly wrote his song “Your Body Is a Wonderland” about her. Hewitt tried to downplay her role in the hit, telling Entertainment Weekly in 2007, “My body is far from a wonderland. My body is more like a pawn shop. There’s a lot of interesting things put together, and if you look closely you’d probably be excited, but at first glance, not so much.”

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Jessica Simpson

The pair dated from 2006 to 2007, but it wasn’t until the aforementioned 2010 Playboy interview that Mayer spoke publicly about his attraction to the “With You” singer. Simpson wrote in her 2020 memoir, Open Book, that she and the singer initially stayed in touch after their breakup, but she deleted his phone number after the Playboy tell-all because she was embarrassed what her grandmother would think of it.

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Minka Kelly

Mayer and the Friday Night Lights alum were briefly linked in 2007.

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Jennifer Aniston

The guitarist and the Friends alum dated on and off from 2008 to 2009. He admitted to Playboy that he slept with “four or five” women while on a break from Aniston and would “always be sorry that it didn’t last” with the actress. A source exclusively told Us Weekly in 2020 that the exes now “have a nice friendship.”

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Taylor Swift

Mayer and the country-pop star briefly dated in 2009 and 2010. She reportedly wrote her song “Dear John” about their ill-fated romance, which Mayer told Rolling Stone was “a really lousy thing for her to do.” Swift’s response? “How presumptuous!” she told Glamour. “I never disclose who my songs are about.”

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Katy Perry

The Dead & Company member and the “Teenage Dream” songstress began dating in 2012 and split in 2014. After telling Chelsea Handler that “you have to go through all this s--t to get your grips on life,” Perry promised that she was no longer going to talk about her ex. “I don’t want to be rude to him … because it always comes to bite me in the ass,” she told Rolling Stone in August 2014. Mayer, for his part, told The New York Times in 2017 that he wrote his single “Still Feel Like Your Man” about Perry.