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Not just Taylor Swift – John Mayer’s celebrity dating timeline: from Katy Perry and Jessica Simpson, to Jennifer Aniston and Jennifer Love Hewitt, ‘Mayer the Player’s longest relationships revealed

Jennifer Aniston, Taylor Swift, Gracie Hunt and Jessica Simpson have all been romantically linked to John Mayer in the past. Photos: @jenniferaniston, @graciehunt, @johnmayer, @jessicasimpson/Instagram; Getty Images

Have you been able to keep up with John Mayer’s dating history? Us neither – after all, it reads like a who’s who of beautiful, talented A-listers who just happen to work in showbiz, too.

But the singer once nicknamed “Mayer the Player” for the speed at which he changed up romantic partners might finally be ready to settle down and tie the knot.

“People don’t think I want to be married. I absolutely want to be married,” he said on an episode of the Comfort Food podcast earlier this month.

Is John Mayer finally ready to settle down? Photo: @johnmayer/Instagram

“You know the secret, which is that I’m actually fairly well-adjusted. And I so badly want to get married if only for my wife to just know in her heart, like, ‘John will know what to do.’ I just think that level of being relied on is the hottest thing in the world to me … You’re a full grown-up when this is your romantic fantasy.”

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Problem is, no such wife exists – but exploiting the 46-year-old’s self-confessed “reliability kink” could very well be the way into Mayer’s heart.

Which begs the question, does this aspiring homebody have a type? Here are just some of the most high profile women Mayer has been linked to over the years …

1. Jennifer Love Hewitt (2002)

Actress Jennifer Love Hewitt poses as she arrives at the Jennifer Love Hewitt, Esquire Magazine and Aids Project Los Angeles 4th annual Oscar viewing party in 2005. Photo: Reuters

Back in the early 2000s when Mayer dated the I Know What You Did Last Summer actress, it was rumoured for some time that the song “Your Body Is a Wonderland” was about Hewitt. Alas, Mayer later clarified that this wasn’t true and it was about his non-famous first girlfriend. Do we believe him?

2. Jessica Simpson (2006-2007)

Jessica Simpson at the Hollywood premiere of The Dukes of Hazzard remake in 2005. Photo: Getty

Simpson and Mayer were romantically linked from 2006 to 2007. Although they reportedly stayed in touch after the break-up, things changed after Mayer’s tell-all Playboy interview went viral. “That girl is like crack cocaine to me,” Mayer said at the time, “Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm. … If you charged me US$10,000 to f*** you, I would start selling all my s*** just to keep f***ing you.’”

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Simpson later wrote in her memoir Open Book that she deleted his number soon after the interview was published. Too right.

3. Minka Kelly (2007)

Minka Kelly later dated Trevor Noah. Photo: @minkakelly/Instagram

The Roommate star briefly dated the singer in 2007, but this time “quietly split” according to media reports.

4. Jennifer Aniston (2008-2009)

Actress Jennifer Aniston attends the premiere of Derailed in New York in 2005 Photo: Getty Images

After her divorce from Brad Pitt, the Friends alum was linked to the guitarist for about a year, per Us Weekly. In his interview with Playboy, Mayer claimed that he slept with “four or five” women while he was on a break from Aniston, before adding that he would “always be sorry that it didn’t last”. We wonder of those two statements may be linked.

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5. Taylor Swift (2009-2010)

Taylor Swift in New York in October 2023 in New York City. Photo: GC Images

Mayer famously dated Swift from 2009 to 2010, and it’s widely rumoured that the country superstar’s song “Dear John” is about their former romance, which was notable for its dramatic age difference: Swift was only 19, and Mayer was 32, when they began their relationship.

“Don’t you think 19 is too young to be played by your dark twisted games, when I loved you so?” Swift sung in the song. Ouch.

6. Katy Perry

Katy Perry was next up on John Mayer’s relationship timeline. Photo: @katyperry/Instagram
Mayer’s longest known public relationship was with “Firework” songstress Katy Perry, whom he dated and-off from 2012 to 2016, per Evening Standard.

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He has publicly said the song “Still Feel Like Your Man” is about Perry.

7. Kiernan Shipka (2022)

In 2018, Kiernan Shipka poses for a portrait in New York to promote her new Netflix series The Chilling Adventures of Sabrina. Photo: Invision/AP

The singer was most recently linked to the Sabrina the Teenage Witch actress in 2022, after they were spotted together in February and November that year, states Popsugar. However, neither party responded to the rumours and they haven’t been spotted together again since 2023, per the source.

So is he single once again? Watch this space …

  • The Strat-toting musician earned the nickname ‘Mayer the Player’ after being linked to a string of high-profile stars over the years, from Taylor Swift – who was 19 when he was 32 – to Jennifer Love Hewitt and Friends’ Jennifer Aniston
  • Mayer has been linked to both Kourtney and Kim Kardashian – but neither relationship was confirmed – and enjoyed his longest romance with pop songstress Katy Perry