Untangling John Mayer's Surprising Dating History

John Mayer was once quite the Casanova of the celebrity dating scene, but not all was as it seemed at every turn for the now older, wiser and increasingly introspective musician.

By Natalie Finn Oct 16, 2021 10:00 AMTags
Watch: John Mayer Breaks Silence on Ex Jessica Simpson's Memoir

John Mayer has said at shows—the kind where you have to zip your phone up in a little locked pouch so the magic doesn't make its way online—that, at this point in his life, he'd just like to meet someone who'll be nice to him.

It's hard to imagine a scenario in which there isn't a line of women eagerly waiting their turn to be nice to the Grammy winner, or to meet him underneath the moonlight for just one night, but obviously dating a guy like Mayer isn't so simple. 

For them or for him.

But the now 44-year-old musician has, in fact, grown more introspective with time, owning up to the fact that he had a reputation as a real hound dog—and acknowledging that he didn't exactly discourage that interpretation of his romantic life. "What has to happen for a guy to believe that he's totally well-adjusted and be that far out of touch?" Mayer reflected to the New York Times in 2017. "My GPS was shattered, just shattered."

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Celebrity Exes You Probably Forgot Existed

He continued, "I'm old enough to look back on my life and go: 'That's probably the photonegative shot in Behind the Music.' Coming up after the break—boom—the downfall."

Of course, it took more than his kiss-and-tell antics to put that hound in the doghouse. Mayer said a lot of stuff before being literally silenced by granuloma on his vocal cords, which required two surgeries, and he ended up accounting for a variety of questionable comments.

But he didn't feel the need to apologize for being an appreciator of women.

Michael Rozman/Warner Bros.

He remembered thinking, when in 2014 he started writing the songs that made up 2017's The Search for Everything, "I'm a young guy. I like girls. I want girls to like me. I want to make music and be thought of as attractive. I was finally ready to re-enter that world and grow back into it."

Turned out, the world he'd left behind was still there waiting for him. 

But though he cut quite the swath through the celebrity dating scene at one point, his intentions questioned at every turn, not all was always as it seemed.

Jennifer Love Hewitt

Their relationship was brief, but Mayer was rumored to have remembered enough about what they did that summer to write one of his biggest hits, "Your Body Is a Wonderland," the second single off his debut album, Room for Squares.

Which came out in 2001 and Hewitt dated Mayer in 2002, so the logic was faulty all along. But the association persisted.

"My body is far from a wonderland," Hewitt protested to EW.com in 2007. "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."

However, settling in for an interview on the podcast Inside of You With Michael Rosenbaum, the 9-1-1 star said that it still wasn't true (as far as she knew) but she was, indeed, flattered that people thought it was. "That's a real compliment," she said.

For his part, Mayer said on VH1 Storytellers that he wrote the song about his first girlfriend from when he was about 14, and he originally called it "Strawberry Wonderland."

Jessica Simpson

After her marriage to Nick Lachey ended, Simpson decided to have a little fun. And she left a mark—on Mayer and the zeitgeist. In 2010, about three years after they split up, Mayer infamously told Playboy, "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."

Well, that was rude. Simpson agreed, and it was indeed a loose-lipped moment Mayer would come to regret. "It's more embarrassing [than anything else], 'cause I'll walk into a restaurant or something and I'll notice more men are looking at me," Simpson, pressed for her reaction, said on The View in 2010. "And he'll never have this napalm again."

When they actually disentangled themselves for good, in June 2007 (with Mayer still shy of 30), a Simpson source told People, "They broke up Sunday night, but who knows what the future will hold. This is the twelfth time they've broken up. Their relationship is volatile. Last week they felt better than ever. This week, things are rocky. Who knows what the future will bring?"

Who could have guessed? Meanwhile, Mayer said on Watch What Happens Live! in April 2020 that, yes, he was aware Simpson had released a memoir and, quoting, Pee Wee's Big Adventure, "I don't have to watch it, Dottie. I lived it."

Cameron Diaz

Moving on from Simpson in 2007, Mayer was briefly linked to the Charlie's Angels star—who memorably lived it up during her bachelorette days before finding her to-have-and-to-hold person in Benji Madden.

She had just broken up with Justin Timberlake earlier that year, so...why not get "super flirty" with Mayer in NYC?

Minka Kelly

The Friday Night Lights star remained friends with the singer after seemingly venturing into more-than territory in late 2007, neither wanting to make a big deal about it.

Jennifer Aniston

Mayer dated the Friends star between 2008 and 2009, more or less off and on from one year's Oscars party to another. But following their initial split that first summer, he informed the world of what happened by ranting to a few paparazzi outside his New York gym, letting it be known that he was "a man who ended a relationship." 

Aniston laughed off her immature ex's antics, telling Vogue, "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. But I feel seriously protective of him and us. Trust me, you'll never see that happen again from that man. And it doesn't take away from the fact that he is a wonderful guy. We care about each other. It's funny when you hit a place in a relationship and you both realize, We maybe need to do something else, but you still really, really love each other. It's painful. There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

They reconciled, but all was done by March 2009. "I'll always be sorry that it didn't last," Mayer told Playboy in that interview the following year. "In some ways I wish I could be with her. But I can't change the fact that I need to be 32."

 

Taylor Swift

Alas, he continued to unknowingly dig the grave for the first chapter of his celebrity life when he tweeted he was working on a song and he wanted to sing it with the 19-year-old Fearless artist. "Waking up to this song idea that won't leave my head. 3 days straight now. That means it's good enough to finish," the once-prolific Twitter user wrote in March 2009. "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."

So, no expectations there at all. But they did meet up to record "Half of My Heart" for his 2009 album Battle Studies, which came out that November, and performed live together several times.

But while he did not make the same mistake he did with Aniston, it was Swift who made sure that people kinda-sorta knew what was what. That he was a man who ended a relationship.

Mayer told Rolling Stone in 2012 that he was pretty devastated by the 2010 song "Dear John," which called out a certain fellow's "dark twisted games." He insisted that, in this case, he "didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that. It was a really lousy thing for her to do."(Swift has never explicitly said that the tune is about Mayer, but before the song came out she said in an interview that "little hints" would assure that it would be clear who the guy was, no further explanation necessary.) 

Moreover, he continued, "I never got an e-mail. I never got a phone call. 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?"

Katy Perry

But things would soon start looking up!

"I actually am dating my crush," Perry told in 2013 of being with Mayer, who she started seeing in 2012 following her divorce from Russell Brand. "I had a crush on him for a long time."

That was after they had already broken up once, however, and their off-and-on love affair ultimately settled into the off position for good in 2015. 

But they were the real deal, and while Perry moved on and found happiness (at first hot and cold, but ultimately full steam ahead) with Orlando Bloom, Mayer took a break from love and found himself stewing a bit.

"Who else would I be thinking about?" he told the New York Times in 2017 when asked about speculation that "Still Feel Like Your Man" was about Perry. "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."

Halsey

After folks wondered whether the "Bad at Love" singer and Mayer were trying to tell them something with their public flirting on social media in 2018, Halsey—at the time, recently split from G-Eazy for the second time—reminded people that not every spark meant a fire was burning.

"I just had a ground breaking idea," they tweeted when the speculation went into overdrive. "What if...we let female artists...have friends...without assuming that they are sleeping together? I know I know. It's like, completely ambitious but like, imagine if we like, tried?"

Wait, you're saying. Done so soon?

Yes, and that's where the surprise lies. While we hardly think Mayer's romantic life has started and stopped with this group, whatever he's up to these days he's taking pains to keep private. "I have nightmares about a second occurrence," Mayer told the Times, referring to the days, peaking in 2010, when he was giving those TMI interviews and insisting that he was just a warm-blooded 32-year-old figuring it out as he went along.

He remained a philosophizer, still prone to grandiose, and sometimes puzzling, statements. He also remained very insistent that he wasn't "that guy," and never really was despite how much he enjoyed talking about his sex life, using lots of metaphors that made it sound deeper than your average bro talk. As he concluded, "I think a lot of people's last impression of me is outdated."

But when a charmed individual left a comment on one of his perpetually endearing Insta posts last summer inquiring why he was still single, his reply said it all: "Google me."