His body is a wonderland. And a busy one, at that.
Earlier this week, John Mayer broke the internet and our brains when he sat down with Cazzie David on his unofficial Instagram live show, Current Mood, and admitted that, when it comes to number of sexual partners, he was in the “sub-500 gang.” And once we realized that he was, in fact, saying “sub-500,” and not “soft 500” as many misheard, we’ll admit, it left us with a whole lotta questions.
First off, how? We’re not in the business of shaming folks for what’s going on in their bedrooms—as long as it’s consensual and no one’s getting hurt, you do you!—but “sub-500” seems as though it’s a pretty large number, no? How does one find enough time in their day, their week, their month, or even their year to woo that many partners? We’re exhausted at the mere thought of it. Our friends over at The Cut did the math and, factoring in an unsubstantiated claim that Mayer lost his virginity at 24 and ignoring any periods of supposed monogamy, it comes out to 25 partners a year and, at most, a new partner every 14.4 days. And we’re going to trust them on that because math makes our heads hurt.
Getty Images; Melissa Herwitt/E! Illustration
Of course, the next question is who? It’s no secret that Mayer’s had quite a few high-profile relationships and flings over the years and, for a while, the whole lothario thing was really his shtick. One that, sure, he’s managed to overcome quite nicely in recent years, but still lingers in our minds, nevertheless. (Never forget the whole “I’ve got a Benetton heart and a f–kin’ David Duke c–k” Playboy interview fiasco of 2010.) And keeping track of a celebrity’s love life—even one as involved as Mayer’s? That’s our thing. Our bread and butter. After all, there’s no math involved there. We were made for this.
So we thought, why not? Let’s give it our best shot and do the damn thing. We present to you our most valiant, scientifically-sound* attempt at cataloging John Mayer’s “sub-500” partners.
*Disclaimer: There is no actual science involved in this. But you knew that. Carry on.
The first bold-type name to join Mayer’s “sub-500 gang” is “A Thousand Miles” singer Vanessa Carlton, whom he romanced in 2001-02 when both were burgeoning stars on the rise. The love affair was brief and barely covered by the media, considering their upstart statuses in the industry, and was mostly forgotten all about until Pitch Perfect 2 came along and reminded everyone that it happened in the first place.
Mayer then moved on to Jennifer Love Hewitt, whom he met in 2002. The romance was brief, as well, and only gained notoriety when rumors began to spread that his first hit “Your Body Is a Wonderland” was written about her. Curiously, however, during an ill-fated attempt at a stand-up comedy career in 2006, Mayer seemed to admit that he never actually got to bed the 9-1-1 actress because of a case of food poisoning brought on by bad fish. He later sent her an apology for the joke.
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Mayer was next linked to The Last Ship actress Rhona Mitra, whom he reportedly hooked up with for a few months in 2005, though neither party has ever confirmed the relationship. The whispers report that he moved from Mitra to actress Milana Vayntrub, who was only 19 at the time. There’s little evidence of this romance, but the rumors persist, so do with it what you will.
His next relationship was a doozy. In 2006, after she split from Nick Lachey, Jessica Simpson dated the musician for nearly a year. And Mayer was not shy about what sort of a relationship they had. In that notorious Playboy interview, he described her as “a drug” and “like crack cocaine to me.” “Sexually it was crazy. That’s all I’ll say,” he continued. “It was like napalm, sexual napalm. Did you ever say, ‘I want to quit my life and just f–kin’ snort you? If you charged me $10,000 to f–k you, I would start selling all my s–t just to keep f–king you.'”
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After Simpson, he had two brief dalliances with Cameron Diaz, on the rebound from Justin Timberlake, and Minka Kelly in 2007, before entering into an on-off relationship with Jennifer Aniston for about a year, which he eventually ended in early 2009. He notoriously held an impromptu press conference outside his New York gym immediately after, where he said, “I’m the a–hole. I burned the American flag. I basically murdered an ideal.” By 2012, he still wasn’t over her. “I’ve never really gotten over it,” he told Rolling Stone that June. “It was one of the worst times of my life.”
He was next linked to future Vanderpump Rules star Scheana Shay—then 23 and known best for her guest appearance on Disney Channel’s Jonas, we guess—who, in a video interview with Just Jared, said Mayer “has really nice lips” and sent her “little messages saying like, ‘Hi, how you doing? How’s your day going?’ It’s like ‘Oooh!’ It’s the little things that makes a big difference.”
Towards the end of 2009, Mayer found himself in a brief romance with Taylor Swift. And that hook-up soured so quickly, it inspired T.Swift’s harsh track “Dear John,” which included lyrics like, “Dear John, I see it all, now it was wrong / Don’t you think 19 is too young to be played by your dark twisted games, when I loved you so?”
In 2011, Mayer was reportedly caught making out with 18-year-old Miley Cyrus at the Grammys, though that reporting came from Star, so take it with a grain of salt. That summer, he added “some girls” to his list when he came across them at a Vegas hotel pool and yadda, yadda, yadda, they all wound up in bed together. “And you know what? It wasn’t smarmy. It was awesome,” he told Rolling Stone of the encounter in 2012. “And then, after that, when I went out that night, I had the greatest time ever, because I was depleted, had no libido left, didn’t have to do any of those crazy Blue Steel looks. It was unbelievable.”
The following year, shortly after she finalized her divorce from Russell Brand, Katy Perry became Mayer’s next conquest. The two recording artists maintained an on-off relationship through 2015, before she began dating Orlando Bloom the following January. And while she moved on from him, she would later rank him a better lover over Bloom or other famous ex Diplo last summer. Mayer’s response? “I don’t have a cool-enough thought for you,” he told Rolling Stone.
Since then, he’s been linked to, well, no one, despite some pretty on-point flirting with Nicki Minaj about a year ago. Calling himself “PR poison” for many people during his IG Live with David, he said, “I find people not being into me brings a real level of reality into my life, whereas when I was in my early 20s where I really couldn’t miss, I kind of abused that. Not so long ago I gave a girl my number and she said, ‘I probably won’t use it.'”
So, that makes 12, right? Like we said, math isn’t our strong suit. As for reaching that sub-500 number, whatever it may be? Our best guess? A whole lotta groupies.
And, yes, we realize we said we had a “whole lotta questions” and only wound up asking about two. We should’ve said we had “sub-500” too. Sue us. (Please don’t. We like our job.)