John Mayer turned heads at a Vogue event in Los Angeles on Wednesday night, showing off graying hair — a far cry from the fresh-faced heartthrob who once dated half of Hollywood.
Now 47, the Grammy-winning singer-songwriter has racked up an impressive romantic resume over the years, including rumored flings with Jennifer Love Hewitt, Jessica Simpson, Taylor Swift, and Katy Perry.
Perhaps most famously, he had an on-and-off relationship with Jennifer Aniston between 2008 and 2009, reportedly reconnecting again in 2019 before calling it quits for good that same year.
But Mayer’s A-list dating streak appears to have cooled in recent years, despite ongoing speculation linking him to Chilling Adventures of Sabrina actress Kiernan Shipka since 2022.
And while age may be slowing down his wild romances, Mayer doesn’t seem to be hiding it.
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John Mayer turned heads at a Vogue event in Los Angeles on Wednesday night, showing off graying hair — a far cry from the fresh-faced heartthrob who once dated half of Hollywood
Still handsome — just a little more seasoned — and clearly still a magnet for Hollywood’s leading ladies, as he posed with Hailey Bieber
And while age may be slowing down his wild romances, Mayer doesn’t seem to be hiding it as he showed off his graying hair; (L in 2006; R on Wednesday)
At the starry event celebrating luxury watchmaker Audemars Piguet, he confidently embraced his salt-and-pepper temples, pairing his silver strands with a laid-back look and a stylish pair of glasses.
Still handsome — just a little more seasoned — and clearly still a magnet for Hollywood’s leading ladies, as he posed with Hailey Bieber.
Back in 2020, Mayer and Aniston made headlines for flaunting their platonic bond, trading likes and friendly comments on social media.
Of course, their original split in 2009 wasn’t exactly smooth.
Mayer raised eyebrows with some blunt remarks about their age difference, telling Playboy at the time: ‘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.’
‘One of the most significant differences between us was that I was tweeting,’ he noted. ‘There was a rumour that I had been dumped because I was tweeting too much.
He added: ‘The brunt of her success came before TMZ and Twitter. I think she’s still hoping it goes back to 1998.’
He went on: ‘If Jennifer Aniston knows how to use BitTorrent, I’ll eat my f**king shoe. One of the most significant differences between us was that I was tweeting…
At the starry event celebrating luxury watchmaker Audemars Piguet, he confidently embraced his salt-and-pepper temples, pairing his silver strands with a laid-back look and a stylish pair of glasses; (pictured with Ginny Wright and Chloe Flower)
Perhaps most famously, he had an on-and-off relationship with Jennifer Aniston between 2008 and 2009, reportedly reconnecting again in 2019 before calling it quits for good that same year; (pictured 2009)
Mayer and Taylor Swift are rumored to have written songs about each other; (pictured in 2009)
The Grammy-winning singer-songwriter has racked up an impressive romantic resume over the years, including rumored flings with Jennifer Love Hewitt, Jessica Simpson and Katy Perry; (pictured with Simpson)
‘There was a rumour that I had been dumped because I was tweeting too much. That wasn’t it, but that was a big difference…’
Speaking herself to Vogue about their split, Jennifer said: ‘He had to put that out there that he broke up with me. And especially because it’s me. It’s not just some girl he’s dating. I get it. We’re human.’
‘It doesn’t take away from the fact that he is a wonderful guy. We care about each other,’ she said at the time.
She concluded, ‘There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that’s where it is.’
Since her split from John Mayer in 2009, Aniston has had only one confirmed relationship and several rumored romances.
Her most significant relationship was with Justin Theroux.
They met in 2011 while filming Wanderlust, got engaged in 2012, and married in a private ceremony at their Los Angeles home in 2015.
The couple announced their separation in 2018 but have remained on friendly terms.
