John Mayer used to be the kiss and tell type. 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 endeavors for men’s magazines such as Play boy. However, after decades of dating in Hollywood, John finally learned to seal his lips.
But that doesn’t mean we’ve forgotten about his star-studded list of ex-girlfriends. Over the years, John dated everyone Taylor Swift on Jennifer Anistonon Jessica Simpson, leaving a trail of paparazzi snaps, breakup songs, and unreal moments to tell for future memoirs. (Taylor’s “Dear John” still cuts like a knife and Jessica’s Open Book is a master class in having the last word.)
While John has learned to bite his tongue these days, in 2017 he joined the New York Times he had “nightmares” about his zip tell-all interviews. “What has to happen for a guy to believe he’s perfectly well adjusted and so far out of touch?” he asked, adding that he is now “old enough to look back” on life and see where the “downfall” is happening.
It’s okay, John. There are many fish in the sea. In the meantime, learn everything there is to know about all his girlfriends, rumored flings, and more here.
Jennifer Love Hewitt
The musician and 9-1-1 star Jennifer Love Hewitt dated shortly in 2002. But their relationship had enough of an impact on John to reportedly 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 are a lot of interesting things together, and if you look carefully you will probably be excited, but at first glance not so much.” She is married to her Love bites co-star Brian Hallisay since 2013, and they have two children together: Autumn and Atticus.
After her marriage to Nick Lachey ended in 2006, was Jessica’s first high-profile relationship with John. The couple broke up the following year. Three years later he famously told Play boy, “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 raunchy interview, and she opened up about her feelings — as well as their allegedly toxic relationship — in her 2020 memoir.
Jessica signed up Open Book that the pressure to be “perfect” for John contributed to her problems with drink. “I was constantly worried that I wasn’t smart enough for him,” Jessica said. He was so smart and treated conversation like a friendly competition that he had to win. “My anxiety would increase and I would pour another drink. This was the beginning of me relying on alcohol to mask my nerves.
After breaking up with Jessica, John dated briefly 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 they broke up in January 2008 and have never spoken about each other in interviews.
John and The Morning Show star dated on and off between 2008 and 2009, and even went to the 2009 Academy Awards together. After their amicable split, John told Play boy that he would “always regret that it didn’t last”.
Their friendship lasted throughout the years, much to the delight of fans. 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 apparently wrote her scathing breakup song 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 all the way home / I should have 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 bad thing to do” that “humiliated” him. “How presumptuous! I never reveal who my songs are about,” Taylor replied 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 piled him on TikTok. As one fan put it, “Funny how Taylor’s one song about you is better than your entire discography.” Ah.
Something Taylor and Katy Perry besides having the same backup dancers in common? 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 was put on the spot the same year, when James Corden asked her to rank her top three exes in bed. John has top billing!