He’s ultra private about his personal relationships now. But once upon a time, John Mayer was all about dating high-profile women in Hollywood — with mixed results. There have been songs written about him, chapters in memoirs, and countless awkward interviews. But still, he perseveres. From Taylor Swift, to Jennifer Aniston, to Jessica Simpson and beyond: take a look back at the famous women John has dated:
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 alleged 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.
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 start of me relying on alcohol to mask my nerves.
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 one another in interviews.
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.
“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,” responded in Glamour.
In 2019, John sent love to Taylor, saying in 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.
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!