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John Mayer used to be the type to kiss and tell. In fact in the 2010s, the “Gravity” singer, 45, was infamous for his TMI interviews about his sex life, eagerly going into detail about his tries for men’s magazines like Playboy. After decades of dating in Hollywood, however, John finally learned to seal his lips, though.
But that doesn’t mean we’ve forgotten about his star-packed list of ex-girlfriends. Over the years John dated everyone from Taylor Swift to Jennifer Anistonto Jessica Simpson, leaving behind a trail of paparazzi snaps, breakup songs, and unreal moments to recount for future memoirs. (Taylor’s “Dear John” still cuts like a knife and Jessica’s Open Book is a masterclass in having the last word.)
While John has learned to bite his tongue these days, in 2017 he told the New York Times he has “nightmares” about his slew of tell-all interviews. “I’ve inherited a younger man’s reputation,” he said. “You can even break ‘bad boy’ into good bad boy and bad bad boy — I somehow managed to become a bad version of a bad boy.”
It’s okay, John. There’s someone out there for you. Ready to learn more about John Mayer’s love life? Check out all of his girlfriends, rumored flings, and more here.
Jennifer Love Hewitt
The musician and 9-1-1 Star Jennifer Love Hewitt dated briefly in 2002. But their relationship had enough of an impact on John to allegedly write “Your Body Is a Wonderland” about her. Jennifer isn’t so sure. “My body is far from a wonderland,” she joked in a 2007 interview with Entertainment Weekly. “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.” She has been married to her Love Bites co-star Brian Hallisay since 2013, and they have two kids together: Autumn and Atticus.
Jessica Simpson
After her marriage to Nick Lachey ended in 2006, Jessica’s first high-profile relationship was with John. The couple split the next year. Three years later, he famously told Playboy, “that girl is like crack cocaine to me. Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm.” Jessica was offended by the crass interview, and she elaborated about her feelings — as well as their allegedly toxic relationship — in her 2020 memoir.
Jessica wrote in Open Book that the pressure to be “perfect” for John contributed to her issues with drinking. “I constantly worried that I wasn’t smart enough for him,” Jessica said. He was so clever and treated conversation like a friendly competition that he had to win. “My anxiety would spike and I would pour another drink. It was the beginning of me relying on alcohol to mask my nerves.
Minka Kelly
After breaking up with Jessica, John briefly dated Friday Night Lights Star Minka Kelly. Their 2007-2008 romance didn’t last too long, but there was no bad blood between the two. Minka and John reportedly remained friends after splitting in January 2008 and have never spoken about each other in interviews.
Jennifer Aniston
John and The Morning Show star dated on and off between 2008 and 2009, even going to the 2009 Academy Awards together. After their amicable split, John told Playboy that he would “always be sorry that it didn’t last.”
Their friendship has endured through the years, much to fans’ delight. John even “liked” a photo of Jen on a fan account in December 2020! Just a few months earlier, she tuned into one of his Instagram Lives and left crying-laughing emojis.
Taylor Swift
“Dear John,” anyone? Taylor reportedly wrote her scathing breakup anthem about the Dead & Company guitarist, whom she dated in 2009 and 2010. Just look at the lyrics: “Dear John, I see it all now that you’re gone / Don’t you think I was too young to be messed with? / The girl in the dress, cried the whole way home / I should’ve known”.
Taylor was 19 during their relationship; John was 30. Taylor denies writing the song about her ex-boyfriend, but that didn’t stop John from telling Rolling Stone in 2012 that it was “a lousy thing to do” that “humiliated” him. “How presumptuous! I never disclose who my songs are about,” Taylor responded Glamour.
In 2019, John sent love to Miss Swift, telling an Instagram Live that he “loved” her romantic song “Lover.” Regardless, a decade later, Swifties are still after John. They dog-piled on him on TikTok. As one fan put it, “Funny how Taylor’s one song about you is better than your entire discography.” Ouch.
Katy Perry
Something Taylor and Katy Perry have in common besides the same backup dancers? They both dated John. Katy and John were together from 2012 to 2014. John confessed in 2017 that he wrote his hit “Still Feel Like Your Man” about Katy. She got put on the spot the same year, when James Corden asked her to rank her top three exes in bed. John got top billing!
