John Mayer’s Romantic History: All The Women He’s Loved From Taylor Swift To Jessica Simpson

With the release of ‘Dear John (Taylor’s Version),’ look back on John Mayer’s past romances, including his relationship with Taylor Swift.

• John Mayer is a Grammy-winning singer-songwriter, known for his versatile abilities to craft both catchy pop-rock songs, and his virtuoso guitar skills, which earned him a place in the band Dead and Co.
• John has dated tons of famous ladies over the years, including Taylor Swift, Jennifer Aniston, and more.
• With the release of ‘Dear John (Taylor’s Version),’ there’s been renewed interest in John’s past relationships.

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 trysts for men’s magazines like Playboy and rock and roll rags like Rolling Stone. After of decades dating in Hollywood, however, John finally learned to seal his lips, but the release of Speak Now (Taylor’s Version), and Taylor Swift’s new version of her devastating breakup song “Dear John,” has led fans to revisit some of the singer-songwriter’s past romances, especially his short-lived relationship with Taylor.

That doesn’t mean we’ve forgotten about all his A-list ex-girlfriends. Over the years John dated everyone from Taylor to Jennifer Aniston, to Jessica Simpson, leaving behind a trail of paparazzi snaps, breakup songs, and wild moments to recount for future memoirs. (Jessica’s Open Book is a masterclass in having the last word.)

While “Dear John” remains a cutting breakup tune, Taylor did ask fans to be kind to its subject at her Minneapolis stop on The Eras Tour, before playing it. While she didn’t name the “Waiting On The World To Change” singer, she told the audience that she had moved on from her past breakups. “I’m 33 years old. I don’t care about anything that happened to me when I was 19,” she said. “I’m not putting [Speak Now (Taylor’s Version)] out so that you can go and should feel the need to defend me on the internet against someone you think I might have written a song about 14 billion years ago.”

While John has learned to bite his tongue these days, in 2017 he told the New York Times he still has “nightmares” about his slew of tell-alls. “What has to happen for a guy to believe that he’s totally well-adjusted and be that far out of touch?” he wondered, adding that now he was “old enough to look back” on life and see where the “downfall” happened.

Asked how he was “still single” during a July 2019 livestream, the guitarist was brutally honest. “Google me,” he quipped with a smile, per, Us Weekly. It’s okay John, you keep searching. In the meantime, learn everything there is to know about 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 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.

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 floored by John’s crassness, telling Oprah Winfrey in 2010, “I tried to read the article and I was so so disappointed in him. It made me so sad and it was really discouraging because that’s not the John that I knew,” per ABC.

Jessica looked back on the relationship in her 2020 memoir Open Book, revealing how 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.”

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. Neither have never spoken about one another 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.”

Talking about the relationship with Vogue in 2008, she said, “He had to put that out there that he broke up with me. And especially because it’s me,” later adding, “It doesn’t take away from the fact that he is a wonderful guy.”

Their friendship seemed to endure, 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 in Glamour not long after.

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. Still, during one of her 2023 concerts, Taylor did ask fans to be nice to the subject of her past songs, as she releases her “Taylor’s Versions” of albums.

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!