John Mayer seems comfortable with his reputation as a serial dater. He once joked to TV host Andy Cohen that Jennifer Lawrence avoids him because of his dating history, while on his Instagram show, Current Mood, Mayer put the number of women he's slept with at "a soft 500." Recently, Jessica Simpson revealed they rekindled their romance "close to nine times" over five years before finally calling it quits.
Back in 2009, Mayer told Ellen DeGeneres that relationships tend to freak him out. “I don't know if you know this, I have sort of a funny track record," he said. "I'm a little freaked out right now about it, to be honest.”
On Instagram, he once posted a black and white photo playing guitar on Instagram, and a fan commented, “Beautiful! How are you still single?” His response was simply, “Google me.”
The 41-year-old is showing no signs of settling down anytime soon.
He slid into popstar Halsey’s DMs in 2018, although Halsey insists the pair are just friends. He was also rumored to be seeing Kourtney Kardashian - but he debunked that theory when he told Andy Cohen on Radio Andy that he thinks Kardashian started the rumor diabolically and said once two people are put together, "You're like, 'Well, if I do [date her], then everything falls into place, because they're already putting us together." He's also close friends with Larry David's daughter, Cazzie, but it doesn't appear that the two are together.
Here's a look at his track record.
The “Your Body Is A Wonderland” years
In the early 2000s, Vanessa Carlton blessed us with the ubiquitous track 'A Thousand Miles,' and she also reportedly dated fellow chart-climber Mayer. They called it quits in 2002, after less than a year. Mayer linked up with actress Jennifer Love Hewitt shortly after.
While Hewitt and Mayer didn't last long together, Mayer’s 'Your Body Is A Wonderland' is rumored to have been written about Hewitt - even though Hewitt herself denied this in a podcast this year.
After the two parted ways, Mayer reportedly kept it in the Hollywood family by dating Hewitt’s Party of Five co-star Rhona Mitra in 2005.
The Jessica and Jen years
Mayer began seeing Jessica Simpson in 2006 after her very public divorce from Nick Lachey. He would later would refer to Simpson as "sexual napalm" in a 2010 Playboy interview.
Simpson said that his "shocking" comments ended their on-off relationship. Speaking to Hota Kotb, she revealed that she had gone back to the singer "nine times" over five years - saying that their relationship was "very complex", but Mayer torpedoed it with the Playboy interview.
She said, "We were great at intimacy. We were great at loving each other. That was easy, but the relationship was very complex."
As for what Mayer said that accidentally ended any hope of them getting back together? Mayer said to Playboy that Simpson was "like crack cocaine to me", adding, "Sexually it was crazy. That’s all I’ll say. It was like napalm, sexual napalm. Did you ever say, “I want to quit my life and just f***ing snort you?
Simpson continued in her memoir Open Book that his comments left her "floored and embarrassed that my grandmother was actually gonna read that."
She continued, "A woman and how they are in bed is not something that is ever talked about. It was shocking. He was the most loyal person on the planet and when I read that he wasn’t, that was it for me. I erased his number. He made it easy for me to walk away."
In the same story, Mayer also discussed his breakup with Jennifer Aniston, who he dated on-and-off from '08 to '09. He set the record straight that his song "Heartbreak Warfare" isn't about the actress, because she's the "sweetest, kindest person," and denied rumors that Aniston dumped him for tweeting too much.
"That wasn't it, but that was a big difference," he said, "The brunt of her success came before TMZ and Twitter. I think she's still hoping it goes back to 1998. She saw my involvement in technology as courting distraction. And I always said, 'These are the new rules.'"
Let's not forget some of his other casual flings from this period, which include: Cameron Diaz, Rashida Jones, and Scheana Marie -- although Mayer reportedly dumped the Vanderpump Rules star after she got a little too candid with the press.
'Dear John' and pop star mania
Mayer might be on good terms with some of his exes, but you can't break Taylor Swift's heart and get away with it. The two musicians famously dated in 2009, at ages 32 and 19 respectively, and Swift reportedly wrote 'Dear John' about Mayer. The song features Swift firing off lyrics like, "Don’t you think 19 is too young to be played by your dark twisted games, when I loved you so?”
Unsurprisingly, Mayer wasn't a fan of the hit and told Rolling Stone in 2012 that he had no idea Swift had felt that way.
"I never got an e-mail. I never got a phone call," he told the magazine. "I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”
He recently discussed Swift's song 'Lover' with Shawn Mendes on his podcast and poked fun at it when he said he loved the song but wanted to change the lyrics. Swifties were unimpressed with his commentary.
He also briefly dated makeup artist Reena Hammer in 2010 and Renee Zellweger in 2011, along with a supposedly secret relationship with actress Shenae Grimes.
Also, long before she broke the Internet, Kim Kardashian was linked to Mayer after they were spotted out in New York in 2010.
Mayer's long-term girlfriend was Katy Perry, who he dated on-and-off from 2012 to 2016. Although they displayed their affection for one another in the video for their collaborative song 'Who You Love,' the couple kept their relationship relatively private.
Mayer admitted to The New York Times that his lovesick song 'Still Feel Like Your Man' is about Perry, appropriately adding: “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.”
We'll give you that one, John.
