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

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Jennifer Love Hewitt

The musician and the I Know What You Did Last Summer actress dated in 2002, and it was long rumored that he wrote “Your Body Is a Wonderland” about her. (In a 2022 interview on the "Call Her Daddy" podcast, however, Mayer revealed that the track was about his "first girlfriend" — not anyone famous.)

In 2007, Hewitt joked that the hit was not about her, telling Entertainment Weekly, “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.” (Mayer, for his part, reportedly penned his 2013 track "Paper Doll" about Swift.)

While Swift attempted to shut down the discussion of her rumored Mayer tracks at the time — which fans have theorized also include even more tracks off of Speak Now, including "The Story of Us," "Ours," and "Superman," as well as later songs like "Would've, Could've, Should've" — her brief romance with Mayer once again made headlines in July 2023 with the release of Speak Now (Taylor's Version).

At one of her Eras Tour stops one month prior, Swift encouraged fans to lead with kindness — and not attack Mayer — while introducing "Dear John." "What I’m trying to tell you is that I’m not putting this album out so that you should go and feel the need to defend me on the Internet against someone you think I might have written the song about 14 million years ago," she told the crowd.

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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.