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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
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

  • 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

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.

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

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
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)

Faye Bradley
Faye Bradley is a Hong Kong-based contributing online editor for Style by SCMP, where she covers topics in luxury, pop culture, celebrity, influencer, entertainment, travel, trending news, food and drinks, and lifestyle. As a freelance writer, her work has been featured in CNN Style, Business Insider, Michelin Guide, Travel + Leisure Asia, China Daily, Design Anthology, BurdaLuxury, Skyscanner, and Hong Kong Tourism Board. With a BA (Hons) in art and design from the University of Leeds, she is the co-founder of Paradigm Haus, a print publication that covers artists, creatives and entrepreneurs the world over, and the founder of CSP Times, a digital luxury lifestyle website. She is also an editor for luxury wellness travel publication Compare Retreats.