Pete Davidson might be this generation’s “lothario”, but millennials had the ever-contentious John Mayer stealing the dating spotlight.
WATCH: John Mayer and Taylor Swift perform together in 2009
The singer, now 45, has been involved in a slew of high-profile relationships with many famous faces. Though, he has confessed he is “surprised” to be labelled a “lothario” and “womanizer”.
But there’s no denying that the Gravity singer has made ~quite~ the mark on his former partners.
We’ve all seen Jennifer Love Hewitt’s cameo in the Your Body Is A Wonderland music video… we’ve cried to Taylor Swift’s John-inspired song lyrics… and we’ve laughed as Katy Perry slid out of her chair after hearing one of his songs.
So, just who has John Mayer dated? Why did the relationships end? And who is his current partner?
Scroll on for all of the answers.
Jennifer Love Hewitt – 2002
It’s unknown how these two met, but they briefly dated in 2002.
Jennifer even starred in John’s video for Your Body Is A Wonderland, fuelling speculation that she inspired the song.
But unlike Benjamin Barry, the actress wasn’t so vain (How To Lose A Guy In Ten Days fans will understand) to think herself the muse.
“My body is far from a wonderland. My body is more like a pawnshop. There’s a lot of interesting things put together, and if you look closely you’d probably be excited, but at first glance, not so much,” she told Entertainment Weekly in 2007.
John confirmed the hit song wasn’t about Jennifer while appearing on the Call Her Daddy podcast in 2022, revealing it was inspired by his high school girlfriend.
“That was about my first girlfriend,” the singer-songwriter said. ”That was about the feeling, which I think was already sort of nostalgic… I was 21 when I wrote that song and I was nostalgic for being 16.”
Jessica Simpson – 2006 to 2007
Yet another double J relationship – John and Jessica dated on-and-off around 2006 to 2007.
After their final split, the Last Train Home singer brought attention to their relationship during a 2010 interview with Playboy where he compared his ex to “crack cocaine”. Jane Austen, eat your heart out.
“It wasn’t as direct as me saying, ‘I now make the choice to bring the paparazzi into my life.’ I really said, ‘I now make the choice to sleep with Jessica Simpson.’ That was stronger than my desire to stay out of the paparazzi’s eye,” John told the publication of his growing fame.
“That girl, for me, is a drug. And drugs aren’t good for you if you do lots of them. Yeah, that girl is like crack cocaine to me … Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm.”
Minka Kelly – 2007
You may remember Minka Kelly as Lyla Garrity from Friday Night Lights. Around the same time she was filming the hit show, the actress struck up a short-lived romance with John.
The pair were spotted hanging out in Austin, Texas, where FNL was filmed. They also attended a Knicks game with Grey’s Anatomy star Ellen Pompeo and partner Chris Ivery.
Their time together lasted a few months, per reports.
Jennifer Aniston – 2008 to 2009
We don’t remember this episode of Friends. John and Jennifer (another double J couple???) reportedly met at the 2008 Oscars after party – and, to quote Taylor Swift, sparks flew.
Apparently they dated for around a year before going their separate ways.
Jen didn’t say too much about the relationship, but John shared his thoughts – implying that their age difference of eight years played a part in their breakup.
The singer had nothing but praises to sing about his ex, deeming her “the most communicative, sweetest, kindest person” to Playboy magazine.
“We just have a regard for each other’s feelings that is pretty intense. It’s been a deep relationship, and it’s no longer taking place at all.”
Taylor Swift – 2009 to 2010
Ahem… speaking of Taylor Swift. We won’t soon forget that these two dated when he was 32 and she was 19.
They met via Twitter in March 2009 when John shoot his shot on the platform.
“Waking up to this song idea that won’t leave my head. 3 days straight now. That means it’s good enough to finish,” he wrote. “It’s called Half of My Heart and I want to sing it with Taylor Swift. She would make a killer Stevie Nicks in contrast to my Tom Petty of a song.”
Having just released her sophomore album, Taylor was starstruck and told Ellen DeGeneres she “freaked out” when reading the tweet.
The pair eventually took the stage together and even released Half of My Heart in June 2009 – performing it at Z100’s Jingle Ball in December, at which point they were “confirmed” to be an item.
John and Taylor then dated until around mid-2010. After their split, the latter songwriter detailed the relationship in ~excruciating~ detail via the song Dear John.
The song’s inspiration himself responded to the track in a 2012 interview with Rolling Stone, saying it was “cheap songwriting” and that he “didn’t deserve” to be called out by Taylor.
“It made me feel terrible. It was a really lousy thing to do,” he said. “I never got an email. I never got a phone call. I was really caught off guard.
“It’s abusing your talent to rub your hands together and go, ‘Wait til he gets a load of this!’ That’s bulls–t.”
Since then, there’s been some subtle tit-for-tats between the two exes – culminating in Taylor’s Midnights track Would’ve, Could’ve, Should’ve (a bop) and John’s appearance on the Call Her Daddy podcast.
You can read our entire breakdown of their relationship right here.
Katy Perry – 2012 to 2014
Although they’ve buried the hatchet now, Taylor and Katy Perry’s former “left shark” feud perhaps wasn’t helped by the fact they both dated the same guy.
Yep, the Firework performer, then 36, was on-and-off with John, then 43, for around four years.
At the start of their courtship, they apparently sent each other love letters. We wonder if John was triggered when he read the words ‘Dear John’ from Katy?
Speaking of being triggered, that’s exactly what Katy admitted to being when a contestant performed one of her ex’s songs on American Idol.
After sliding out of her seat, the judge admitted: “I’m triggered! It’s a great song. You did great, but I can’t talk anymore.”
Now, Katy has found Orlando Bloom and Taylor has found Joe Alwyn. AND their feud has been laid to rest – we love to see it.
Kiernan Shipka (allegedly) – 2022
In November 2022, John, 45, was spotted leaving the same Italian restaurant as Chilling Adventures of Sabrina star Kiernan Shipka, 23.
Eyewitnesses claimed the pair spent four hours together during the dinner. Though they reportedly left in separate vehciles.
John, for his part, denounced the concept of dating entirely on the Call Her Daddy podcast in December 2022.
“Dating is no longer a codified activity for me, it doesn’t exist in a kind of… It’s not patterned anymore,” the Waiting On the World to Change singer said, explaining that sobriety played a big part in his decision.
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