John Mayer Dating History
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A Closer Look at John Mayer’s Rich Dating History


| LAST UPDATE 04/16/2023

By Abby Wall

John Mayer opens the lid on his love life, finally addressing his infamous "womanizer" label, and explains why he's currently not dating! But first, let's take a look at all the ladies Mayer has dated…

John Mayer

We know him, and we sure do love him - the one and only John Mayer. Since the early 2000s, he's been considered the ultimate heartthrob, but he's also been known to be the ultimate heartbreaker!

John Mayer Dating HistoryJohn Mayer Dating History
Instagram via @johnmayer

Since his rise to fame, the artist has dated some of the biggest names in the biz, earning the unofficial title of Hollywood's Casanova. However, in a recent and rare interview with Alex Cooper on Call Her Daddy, the musician opened up about his previous dating habits and what's stopped him from going out on the town in recent years.

Musical Success

Born and raised in Connecticut, Mayer was always destined for success. After attending the Berklee College of Music, he moved to Atlanta with Clay Cook to form a band. But after their split, Mayer continued to perform at local clubs, which evidently led him to his first major gig at South by Southwest in 2001.

John Mayer Dating HistoryJohn Mayer Dating History
Instagram via @johnmayer

Mayer was signed immediately after to Aware Records and released Room for Squares (2001) and Heavier Things (2003), which received an unbelievable response from critics and audiences worldwide. From then on, Mayer became a household name in music, eventually making him the latest "it boy" in Hollywood.

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Hound Dog Reputation

Mayer has also garnered a rather personal dating resume throughout his professional career, becoming known as a "womanizer" for his bachelor lifestyle. He was a young rockstar who happened to be extremely attractive. So naturally, he was in the headlines for his "scandalous" dating life.

John Mayer Dating HistoryJohn Mayer Dating History
Instagram via @johnmayer

"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," he said while writing the music for The Search for Everything album. The 2017 album was home to some of Mayers' top hits, such as Love on the Weekend and Rosie.

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Hollywood's Casanova

In a recent interview with Alex Cooper on Call Her Daddy, the Grammy award winner addressed his womanizer past, explaining where it all started. As he told the podcast host, he was "made to believe" from a young age that when a woman expressed any romantic interest, it was "pretty much on accident."

Call Her Daddy John MayerCall Her Daddy John Mayer
Instagram via @johnmayer

So what did he do? He learned to "capitalize" on it pretty quickly, but in reality, he doesn't feel like that's his character at all. "That is what that is," he said of the womanizer label. "That's the role I play on the big TV show I didn't write, but that's fine. Maybe I had a hand in it or something," he admitted.

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Infamous Dating Roster

And look, it all checks out - he's a gorgeous rockstar! Who wouldn't want to date John Mayer? He's a wizard on the guitar, has the voice of an angel, and looks like a supermodel - what a combination! Since his first high-profile relationship in the early 2000s, Mayer has racked up quite the dating resume (and infamous dating label).

John mayer dating relationshipsJohn mayer dating relationships
Instagram via @johnmayer

Although he's recently revealed that he's not "really dating" anyone, it doesn't take away from the fact that he was once the most desired man to date in Hollywood! So, let's take a closer look at his particularly rich and lengthy dating history and some of the music these lovely leading ladies inspired.

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Vanessa Carlton

It was the early 2000s, and life was simple. There was no social media, low-rise jeans were in, and Vanessa Carlton's hit song A Thousand Miles was on repeat. John Mayer had just released new music, and the world was loving every minute of it.

John Mayer Vanessa CarltonJohn Mayer Vanessa Carlton
 L. Cohen/WireImage via Getty Images

So naturally, the two Billboard chart successes would find each other! Carlton and Mayer were spotted a few times together throughout their relationship, and had reportedly dated for a year before calling it quits. Carlton later called her ex a "bad breaker-upper."

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Jennifer Love Hewitt

Following his break up with fellow musician Vanessa Carlton, Mayer began dating Ghost Whisperer star Jennifer Love Hewitt! Although they briefly dated in 2002, there was much speculation around Hewitt being the inspiration for one of his most famous hits; Your Body is a Wonderland.

John Mayer Jennifer Love HewittJohn Mayer Jennifer Love Hewitt
Bauer-Griffin/GC Images via Getty Images

"My body is far from a wonderland," Hewitt told in 2007. "My body is more like a pawnshop," she joked. Although she considered the rumors a "real compliment" that the hit song was about her, Mayer recently confessed the song was actually about a high school girlfriend and not about any one of his starlit girlfriends.

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Your Body is a Wonderland

And as flattered as she was that people thought the song was about her, it turns out it was not! "That's a real compliment," she said to Michael Rosenbaum on the Inside of You podcast. According to Mayer, the song was "about my first girlfriend," and he had "never met a celebrity" when he wrote the tune.

John Mayer Body WonderlandJohn Mayer Body Wonderland
YouTube via John Mayer

"I was 21 when I wrote that song, and I was nostalgic for being 16," Mayer told Alex Cooper. In fact, the song was initially called Strawberry Wonderland before being switched to Your Body is a Wonderland. And that was just the first of many love songs the artist would release…

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Jessica Simpson

After his break up with Hewitt, Mayer began dating Hollywood's "it girl" Jessica Simpson. Following her divorce from Nick Lachey, the couple was first spotted on New Year's Eve together in New York City before going public in 2007. Although they famously broke up and got back together many times, they kept their relationship pretty lowkey.

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 Paul Kane via Getty Images

An inside 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?" John apparently broke up with Jessica nine times over email!

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The Playboy Interview

Hollywood's favorite couple of 2007 eventually broke up once and for all, and according to Simpson's memoir, Open Book, they stayed in touch after their breakup. However, it was Mayer's 2010 interview with Playboy that changed the course of that relationship.

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 James Devaney/WireImage via Getty Images

The Gravity crooner infamously gave a tad too many personal details about his and Jessica's love life. "Yeah, that girl is like crack cocaine to me," Mayer revealed in the interview. "Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm." And, well, that really didn't roll over well.

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Jessica's Reaction

"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 said on The View in 2010 in response to her ex's hurtful comments. "And he'll never have this napalm again," she added!

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 Kevin Mazur/WireImage via Getty Images

The Dukes of Hazzard star later talked about John's Playboy interview and their relationship in her 2020 memoir. "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."

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Dating a Charlie's Angel

It was on to the next for John Mayer, Hollywood's hottest bachelor! After Mayer's breakup with Simpson in 2007, the Free Fallin' singer began dating another Hollywood it girl, Cameron Diaz. The Charlie's Angel star had just broken up with Justin Timberlake and fell right into John Mayer's arms.

Cameron Diaz John MayerCameron Diaz John Mayer
 Jim Smeal/BEI via Shutterstock

According to People magazine, the couple first linked up in NYC at the famous Bowery Hotel, and they were "super flirty" with one another. Although their flirtation didn't last very long, it definitely checked out that two of Hollywood's finest found each other for a little flirtation before moving on to the next one.

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Minka Kelly

Room for Squares, Heavier Things, and Continuum are all out, and John Mayer is at the top of the charts (and basically the world). At this point, he's gained the "womanizer" label around town, raking up a hot Hollywood dating profile- so who would be next?

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 James Devaney/WireImage via Getty Images

Fresh off his fling with Cameron Diaz, the guitarist was spotted hanging out with Friday Night Lights star Minka Kelly. The couple was spotted together at some Los Angeles hotspots but eventually decided to break it off because he allegedly wasn't looking for anything serious at the time.

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Jennifer Aniston

One of his most high-profile relationships began in 2008 when the Grammy Award winner dated the one and only Jennifer Aniston. Before dating the Gravity singer, Aniston was in a long-term relationship with Brad Pitt and took some time off the dating scene before publicly dating Mayer.

Jennifer Aniston John MayerJennifer Aniston John Mayer
Matt Baron/BEI via Shutterstock

The handsome couple dated on and off between 2008 and 2009, but there were more than a few bumps in the road. The Slow Dancing in a Burning Room singer later admitted to Playboy that while he and Aniston were on their "off period," he was sleeping with multiple women.

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Calling It Quits

Following their first split, Mayer decided to make it known that he had initiated the breakup. The guitarist decided to relay the message to a few paparazzi outside his gym in New York, letting them know he was "a man who ended a relationship."

Aniston John Mayer relationshipAniston John Mayer relationship
John Parra/WireImage via Getty Images

The Friends star later responded to his antics by saying, "He had to put that out there that he broke up with me." She added, "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."

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No Malicious Intent

She continued to share with Vogue that regardless of their very public break up, there's still a lot of love between them. "And it doesn't take away from the fact that he is a wonderful guy. We care about each other," the Murder Mystery star said.

Aniston John Mayer datingAniston John Mayer dating
Kevin Mazur/VF/WireImage for Vanity Fair via Getty Images

"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," she added. "There was no malicious intent. I deeply, deeply care about him; we talk, we adore one another. And that's where it is."

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Regrets, Regrets, Regrets

Despite their on-and-off relationship, the two A-listers decided to call it quits once and for all by March 2009. However, that doesn't take away from the fact that Mayer might have wished for a different outcome. He told Playboy the following year, "I'll always be sorry that it didn't last."

Aniston John Mayer timelineAniston John Mayer timeline
 Arnaldo Magnani via Getty Images

"In some ways, I wish I could be with her," he added. But, however sorry he was, he also said," But I can't change the fact that I need to be 32." However, an inside source told Us Weekly in 2020 that they "have a nice friendship." We love to hear it!

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Scheana Shay

We know her as one of the stars of Bravo's Vanderpump Rules, but back in 2008, she was the lucky waitress that caught John Mayers attention. Years later, the reality star shared she linked up with the musician after waitressing at a party he was hosting while he was dating Aniston.

Scheana Shay John MayerScheana Shay John Mayer
Instagram via @scheana

Following his split with Jen, he met Shay and Stacie Adams from The Hills, and they hooked up. "This went on for about six months, that we hung out," she told the Flashback podcast. "We had a little throuple going on." However, Scheana got fired after management found out, and she went on to work at Villa Blanca!

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Taylor Swift

Mayer continued on to date another one of Hollywood's it girls, Taylor Swift. The songstress is known for dating some of Hollywood's finest, but she is also known for writing songs about them post-break-up, and well, John Mayer would soon become one of them.

Taylor Swift John MayerTaylor Swift John Mayer
 Kevin Mazur/WireImage via Getty Images

The couple dated in 2009 when she was just 19 and Mayer was 32. They met after working together on the single Half of My Heart, which would eventually be featured on Battle Studies. At the time, she told Elle she had “been such a big fan of John for such a long time” and was “really excited” to work together.

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Music Meets Romance

After their single was released, Swift and Mayer performed together at Jingle Ball in New York City, and fans quickly suspected a romantic connection-and; well, they were right! Not only did the couple evolve romantically, but musically, it felt like they were made for each other.

Swift John Mayer relationshipSwift John Mayer relationship
Dimitrios Kambouris via Getty Images for VEVO

Their working relationship began when he tweeted he was working on a song and wanted "to sing it with Taylor Swift." And so they did. And even once they broke up, Mayer praised her talent when he presented her with an award, saying, "You could put her in a time machine in any era, and she would have a hit record."

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Dear John

Following their break up, Swift did what she does best; she turned their breakup into a song. The Love Story singer penned the iconic song, Dear John, featured on her 2010 album, Speak Now, and well, it was clearly about her ex, John Mayer. The singer later told Rolling Stone that he was "really humiliated" by her song.

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 Dimitrios Kambouris/WireImage for Clear Channel Radio New York via Getty Images

He claimed that he is "pretty good at taking accountability now" and that he "never did anything to deserve that [song]," adding, "It was a really lousy thing for her to do." Mayer continued to share that he "was really caught off guard" by the song's release, considering he was already "dressed down" by the public over the breakup.

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Paper Doll

So, what did John Mayer do in response to Swift's song, Dear John? The guitarist released a rebuttal song three years later, Paper Doll. As soon as the song was released, fans put together the pieces about who it was about. And with many references to his ex, the mystery was quickly solved: it was about Swift.

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 Larry Busacca/WireImage for Songwriter's Hall of Fame via Getty Images

Mayer directly responded to lines of Swift's Dear John in Paper Doll. For example, Mayer's line, "Someone's gonna paint you another sky," is a shot at her lyric, "You paint me a blue sky and go back and turn it to rain." Audiences also figured Mayer's line referencing "22 girls in one" is connected to Swift's single, 22.

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Katy Perry

After all the Taylor Swift backlash, things made a sharp turn when Katy Perry entered the picture. The American Idol judge dated Mayer on and off from 2012 to 2015, which was the guitarist's longest public relationship. "I actually am dating my crush," she told W in 2013.

Katy Perry John MayerKaty Perry John Mayer
Christopher Polk via Getty Images for NARAS

And things were looking good for the artistic duo; they were constantly on red carpets together, showing affection for one another, and people were rooting for them as a couple. He told CBS News Sunday Morning, "For the first time in my life, I don't feel like I'm in a celebrity relationship."

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The One That Got Away

However, turns out all good things do come to an end. The couple called it off for the last time in 2015, and Perry moved on and began dating her now husband, Orlando Bloom, the following year. Unfortunately for Mayer, he wasn't ready for much moving on and instead took his feelings to song.

Katy Perry John Mayer relationshipKaty Perry John Mayer relationship
Kevin Mazur/WireImage via Getty Images

In 2017, Mayer released the song Still Feel Like Your Man, which he openly admits was written 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," he told the New York Times.

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Kiernan Shipka

After taking a long hiatus from the dating scene, Mayer finally returned to the dating scene! His heart was broken after all. The singer was first spotted hugging Mad Men star outside the Tower Bar in Los Angles over a year ago, but their relationship was never confirmed.

Kiernan Shipka John MayerKiernan Shipka John Mayer
JM HAEDRICH/SIPA via Shutterstock

A few months later, Mayer and Shipka, who happens to be over twenty years younger than the musician, were spotted having an intimate dinner together in Santa Monica, California. Eyewitnesses reported the two spent four hours together and seemed very into each other. However, as of December 2022, Mayer has stated he is single.

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Looking for the One

Despite his dating history and "womanizer" label, Mayer has recently come clean about his dating intentions and relationships. In a very out-of-the-ordinary interview, Mayer told the Call Her Daddy host, "Every relationship I've been in was devoted to the idea that this could go the distance," which surprised many listeners.

John Mayer relationship datingJohn Mayer relationship dating
Instagram via @johnmayer

"My entire life, today included, if you told me I could have a great two months with someone, but it would end on the first day of the third month, I would not be interested. I've always sought potential for long-term relationships. I know what my mistakes were looking back, not worth talking about," he told Cooper.

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The Spotlight

In fact, in a 2021 interview with Andy Cohen, John was asked what remains on his bucket list. "There's one thing left, and that's [having a] wife and kids," he said. "That would complete all of it." So, it's clear he was looking for an everlasting relationship. Still, it was a challenging task with being the center of attention his whole career.

John Mayer celebrity dating John Mayer celebrity dating
Instagram via @johnmayer

"As long as you're aware of what those things are and how you can apply that to the next relationship, I don't see a problem with any past relationships ending badly," he says. "Mine are different because they are well known." And, well, his relationships were extremely well-known!

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Liquid Courage

During his tell-all interview with Alex Cooper, Mayer told the podcast host that he doesn't "date that much" anymore. The 45-year-old musician said, "I look at it like this: Dating is no longer a codified activity for me… It's not patterned anymore."

John Mayer dating relationshipsJohn Mayer dating relationships
Instagram via @johnmayer

However, according to Mayer, a big reason for not dating anymore is his decision to become sober. "I don't really date — I don't think that I have to, to be quite honest. I quit drinking like six years ago, so I don't have the liquid courage. I just have dry courage," Mayer added.

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Conflict Resolution

So, after all these years, Mayer was always looking for the one. And although he garnered this "womanizer" label, he was searching for something more. So, when Cooper asked the Still Feel Like Your Man singer if he was afraid of commitment, he immediately responded, "Nope."

John Mayer relationship historyJohn Mayer relationship history
Instagram via @johnmayer

He told the podcast host, "Of course, I want to get married." He even explained what he hopes for in his marriage, including the more mundane fights, like arguing over the dry-cleaning. "Nothing's hotter to be than conflict resolution," he added.

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What's Next?

Although Mayer's dating life has taken a backseat the past few years, he told Alex Cooper that he's always believed in that forever love! So, after years and years of dating around, it sounds like Mayer was looking for the same thing as the next person-he just happened to be center stage.

 John Mayer relationship timeline John Mayer relationship timeline
Instagram via @johnmayer

In the interview, he told Cooper he is currently single, so we hope he is ready to mingle! We're hoping John finds his leading lady soon that he can write love songs about and get into those boring fights over cleaning the dishes with.

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