The Truth About John Mayer's Celebrity Ex-Girlfriends

John Mayer has one of the most storied dating histories in Hollywood today. The 43-year-old songwriter has earned himself a reputation, not just for dating famous women but for saying the exact wrong thing about the relationships in the media.

Mayer's history of dating famous women began early in his career. He reportedly dated fellow up-and-comer Vanessa Carlton in 2002 for less than a year before they went their separate ways (per Evening Standard). Next up was actress Jennifer Love Hewitt, who he dated from 2002 to 2003. Mayer reportedly wrote his hit single, "Your Body Is A Wonderland," about her (per More).

The next few years saw Mayer making the most of his bachelor status. He was dating around, spotted with many different models and actresses, but none for too long. It wasn't until 2007 he met a woman who stopped him in his tracks, singer and actress Jessica Simpson.

Things between John and Jessica were complex, to say the least

In her memoir Open Book, Simpson opened up a lot about her relationship with Mayer. They first started seeing each other shortly after her divorce from Nick Lachey in 2006 (per Refinery29). Simpson revealed that they broke up nine times and each time, Mayer ended things with her by email. 

Mayer famously crossed the line by referring to Simpson as "sexual napalm" in a 2010 Playboy interview (per Us Weekly). She claimed that was the last straw in their back and forth. "He was the most loyal person on the planet and when I read that he wasn't, that was it for me," Simpson wrote in her memoir (per Evening Standard). "I erased his number. He made it easy for me to walk away."

Mayer had no problem moving on to another major name whose relationships were constantly making headlines: actress Jennifer Aniston.

John dated Jennifer for just over a year

Mayer and Aniston got together in 2008, after he was rumored to be involved with Cameron Diaz and Minka Kelly (via More). Mayer and Aniston only lasted about a year in their relationship before splitting. When they did break up, rumors flew that the age difference between the two was a factor (via Marie Claire). Though Mayer denied Aniston dumped him for tweeting too much specifically, he did hint that she wasn't thrilled with his relationship with technology in the same Playboy interview where he discussed his relationship with Simpson.

"I'll always be sorry that it didn't last. In some ways I wish I could be with her. But I can't change the fact that I need to be 32," he said. Of a rumor that they broke up over him Tweeting too jmuch, he added, "That wasn't it, but that was a big difference. The brunt of her success came before TMZ and Twitter. I think she's still hoping it goes back to 1998. She saw my involvement in technology as courting distraction. And I always said, 'These are the new rules.'"

2009 saw Mayer have some flings with some famous names. He was linked to Vanderpump Rules star Scheana Marie and actress and writer Rashida Jones. 

In 2009, John crossed paths with Taylor Swift

Mayer shocked many with his next high profile relationship. In 2009, he began dating fellow singer-songwriter Taylor Swift. She was 19 years old at the time, while he was 32 (per Evening Standard). Swift wasn't shy about the fact that the breakup was not amicable. In her song "Dear John," she wrote, "Don't you think 19 is too young to be played by your dark twisted games, when I loved you so?" (per Genius).

That was far from Mayer's last famous fling, however. After Swift, he was linked to Miley Cyrus, Kim Kardashian, and Reena Hammer (per More). There was one more famous songstress in his sites, however. In 2012, rumors began circulating that Mayer was seeing Katy Perry, fresh off her divorce from Russell Brand. Mayer and Perry waited some time to confirm that they were an item. She discussed it when talking about the track "Legendary Lovers" off her album Prism.

"I actually wrote it in an email one time, and after I wrote it I looked — we had a long courtship before anything was [public], just writing letters to each other — and seeing 'legendary lovers,' it sounded so nice," she told Entertainment Weekly. "Some things float into my mind, and I process them, and [then] I make songs about them."

Katy and John were also on and off

Like his other relationships, things between Mayer and Perry were rocky. The two reportedly split three different times between 2012 and 2016. "I was madly in love with him. I still am madly in love with him," Perry told Rolling Stone during one of those break-ups in 2013. "All I can say about that relationship is that he's got a beautiful mind ... Beautiful mind, tortured soul. I do have to figure out why I am attracted to these broken birds."

Since their split, Mayer hasn't dated much. He acknowledged the fact when asked about his 2017 song, "Still Feel Like Your Man," which he admitted was about Perry. "Who else would I be thinking about?" Mayer told The New York Times. "And by the way, it's a testament to the fact that I have not dated a lot of people in the last five, six years. That was my only relationship. So it's like, give me this, people."

Perry has moved on with actor Orlando Bloom. The two welcomed a daughter, Daisy Dove, in August 2020 (per Today). As for Mayer, he's been linked to ladies such as Halsey, Jennifer Lawrence, and Cazzie David. He's quick to shoot down rumors, leading many to believe he's been single since he and Perry called it quits.