John Mayer: The man that dates the most powerful women in the world.


Singer-songwriter John Mayer is almost as famous for his relationships as is he for his catalogue of chart-toppers.

In fact, several of the latter are believe to be inspired by the well-known women he’s dated over the years.

And somehow, it seems the singer has a real knack for dating the most powerful women in the world, often when they’re at the pinnacle of their careers.

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Need a refresher? From Jessica Simpson to Renée Zellweger, here are all the singers and actors that John Mayer has gone out with.

Jennifer Love Hewitt

Jennifer Love Hewitt in 2002. Image: Getty.

The early '00s TV star dated John Mayer in 2002. Their relationship was widely talked about, as a rumour suggested his hit song, Your Body is a Wonderland, was written about her.

However, Jennifer later denied this, sharing that the song was in-fact written before they met.

Jessica Simpson

Mayer with Jessica Simpson in 2006. Image: Getty.

Following her divorce from Nick Lachey, singer Jessica Simpson dated John Mayer on and off for a year in 2006. In 2010, he described her to as "sexual napalm" to Playboy.

"Yeah, that girl is like crack cocaine to me. Sexually it was crazy," he said. "That's all I'll say. It was like napalm, sexual napalm."

In her new memoir, Simpson reflected on the "shocking" quote.

"He thought that was what I wanted to be called. I was floored and embarrassed that my grandmother was actually gonna read that."

She wrote that Mayer told her "again and again" throughout their relationship that he was "obsessed" with her, "sexually and emotionally".

Cameron Diaz

cameron diaz
Cameron Diaz in 2007. Image: Getty.

In 2007, Cameron Diaz and Mayer had a brief thing. Diaz had just ended her relationship with Justin Timberlake, and Mayer and Simpson had only recently called it quits, so the two went out for dinner and drinks in New York City.

Although there are no comments stating it was anything more than a date, People shared that it got "super flirty".

Jennifer Aniston 

Mayer with Jennifer Aniston in 2008. Image: Getty.

The pair met at an Oscars party in early 2008 and, soon after, they were dating. Mayer was spotted flying to Miami to meet Aniston, where she was filming Marley & Me. And almost immediately, the Friends star and the singer were plastered across every magazine cover.

Speaking about their high profile relationship with Popsugar, Mayer shared, “I had a conversation about fame with Jen before we ever really stepped out in public. She said, ‘Do you understand what this entails?'

“Two weeks later I had people outside my house. I was smart enough to know it would probably make me a salable item for the paparazzi. I knew I’d have to move to a home that had a gate.

"But that pearl of possibility that lives in your heart when you meet somebody you want to know more about has such a different molecular density than everything else, that you have to pursue it. And I wouldn’t undo it, man.”

Only a few months after their relationship began, the pair stopped dating in August 2009. Mayer shared that the age difference (Aniston was eight years older) played a major role.

In a 2010 interview with Playboy, he said, “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.”


On the plus side, it seems the two remain close, as Mayer attended Jen's 50th birthday party last year.

Taylor Swift

Taylor Swift in 2009. Image: Getty.

Rumours began circulating in 2009 that the 18-year-old, emerging country artist Swift was dating 32-year-old Mayer. Although no pictures confirm this, she later wrote a song titled, Dear John, with lyrics that read, "Don't you think I was too young to be messed with?"

Considering Taylor's songs are known to include details about who she's dating, it's widely believed two were definitely seeing each other, if only for a little while.


Miley Cyrus

miley cyrus
Miley Cyrus in 2011. Image: Getty.

This was only a very brief affair. When Miley was 18, she was spotted kissing Mayer backstage at the 2011 Grammy Awards.

Renée Zellweger

Renee Zellweger in 2011. Image: Getty.

It was confirmed by Page Six that Zellweger and Mayer were discreetly dating briefly in May 2011.

Katy Perry

Mayer and Katy Perry in 2014. Image: Getty.

Musicians Katy Perry and John Mayer dated on and off for three years. Since starting their relationship in 2012, the pair broke up three times until they finally called in quits in 2015.

During that time, they performed together multiple times and co-wrote a song, titled Who You Love.

When Ellen Degeneres asked about the relationship, Mayer shared, "Listen, it was a very private relationship going in. It was a private relationship during, and it's a private relationship still," he said.

In 2017, Mayer confirmed the song Still Feel Like Your Man was indeed about ex Katy Perry.

Speaking to The New York Times he said, “Who else would I be thinking about?

"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.”

Lastly, although nothing has been confirmed, it was rumoured that he went on dates with Kim Kardashian, Shenae Grimes and Demi Lovato, too.

Last anyone heard, John Mayer is currently single.

Feature image: Getty.