John Mayer was born with a musical gift. From his vocals and guitar playing to his passion and songwriting, Mayer was destined to perform. However, there is one thing about the singer that seems to overshadow his natural-born talent and successful career: relationships! Like many other artists, Mayer has admittedly used his fame to get girls.
John Mayer has been linked to a string of Hollywood ladies over the years. From actresses to supermodels, Mayer doesn’t seem to be lacking in that area. From Jennifer Aniston to Kim Kardashian, there are plenty of starlets you didn’t realize hooked up with Mayer.
Check out John Mayer’s relationship timeline. Plus, we added some interesting facts about the singer.
Vanessa Carlton: 2002
Back in the early 2000s, John Mayer dated the beautiful Vanessa Carlton. The pair met as they started their musical careers and paved their way to stardom! Carlton is best known for her hit song A Thousand Miles. Their whirlwind romance wasn’t meant to be.
Their short-lived relationship didn’t even last a full year before the singing duo called it quits in 2002. John set his sights on the stunning actress Jennifer Love Hewitt. Nowadays, Carlton is married to John McCauley. The couple couldn’t be happier and in 2015, they had a baby girl named Sidney.
Jennifer Love Hewitt: 2002 – 2003
Almost immediately after parting ways with Carlton, John Mayer was head over hills for the Ghost Whisperer actress Jennifer Love Hewitt. However, their relationship seemed to have fizzled out before anyone even knew they were dating. The reason for their breakup is unclear.
When the two were still together in 2002, Mayer released his second single Your Body Is a Wonderland, which is believed to have been written about Hewitt. The actress responded to the rumors in an interview with Entertainment Weekly: “My body is far from a wonderland. My body is like a pawn shop.”
Rhona Mitra: 2005
It has never been confirmed (or denied) that the pair actually dated, but back in 2005, there were rumors about British actress Rhona Mirta hooking up with Mayer for a few months. Apparently, both parties tried to keep their affair under wraps…
Whether it was a fling or a full-blown relationship, Mayer and Mitra eventually ended things. Mitra went on to have an impressive and successful acting career, while Mayer spends his time serenading the women of Hollywood and making them swoon! His next victim was Milana Vayntrub.
Milana Vayntrub: 2006
Actress and comedian Milana Vayntrub is one of John Mayer’s many casual flings. Apparently, the starlet was only 19 years old when rumors started circulating that she was hooking up with the 28-year musician. Clearly, he has a type (but we’ll talk about that later).
Vayntrub is mostly known for her role on Days of Our Lives, but she went on to have a remarkable career. She has also appeared on eight episodes of the hit show This Is Us, playing Sloane Sandburg. She has certainly come a long way since crossing paths with Mayer.
Jessica Simpson: 2006
Jessica Simpson’s marriage to Nick Lachey was extremely memorable thanks to their reality show, “Newlyweds: Nick and Jessica.” Unfortunately, the only thing more notable was their very public divorce. That’s when Simpson and Mayer dated for almost a year!
However, they had a seemingly messy breakup. When the pair split, Mayer gave the tabloids pure gold when he compared Simpson to “crack cocaine” during a Playboy interview. The shameless singer even said that “sexually it was crazy,” and he didn’t stop there. He went on to say, “Did you ever say, I was to quit my life and just f*ckin snort you? If you charged me $10,000 to f*ck you, I would start selling all my sh*t just to keep f*cking you.”
Cameron Diaz: 2007
After his split with Jessica Simpson, Mayer was seen flirting with beautiful, blonde actress Cameron Diaz. At the time, she and Justin Timberlake had just called it quits, so it looks like they both needed a rebound. Although they were both ready to start something new, it wasn’t meant to last.
Reportedly, Mayer had real feelings for Diaz, and it wasn’t just a hookup like the other women in his past. However, many people kind of forget about this relationship since it faded quite quickly. Diaz is now married to Benji Madden, and the pair have one daughter together.
Minka Kelly: 2008
In the fall of 2008, Mayer began casually dating Derek Jeter’s ex and Friday Night Lights actress Minka Kelly. The two were spotted together in Austin, Texas – where the show was being filmed – and were later seen hanging out in Los Angeles.
Reportedly, the romance ended just a few months after they started dating. Mayer moved on to date another beloved Hollywood actress, Jennifer Aniston. Kelly has been doing well for herself with a successful acting career. She even had a three-episode guest appearance on Jane the Virgin, playing Abbey Whitman.
Jennifer Aniston: 2009
After meeting at an Oscars party, John Mayer and Jennifer Aniston were dating on-and-off for about a year back in 2009. They eventually broke up for good, but Mayer apparently wrote the song Shadow Days about Aniston. He still feels bad about their breakup years later and indicated age may have been a factor.
“That woman was the most communicative, sweetest, kindest person,” the singer revealed in an interview with Playboy. “I’ll always be sorry that it didn’t last. In some ways, I wish I could be with her. But I can’t change that fact that I need to be 32.”
Scheana Marie: 2009
John Mayer and Scheana Marie may or may not have dated in 2009. Mayer completely denied having any sort of relationship with Marie. However, the reality star said otherwise. Just Jared once asked her if the legendary womanizer John Mayer was a good kisser.
The gushing starlet said that she liked his lips. She dropped a few other subtle hints throughout the interview suggesting she and Mayer had been intimate. I guess we’ll never know the truth. Since then, Marie has made a name for herself starring on the hit Bravo reality show, Vanderpump Rules.
Taylor Swift: 2009
John Mayer is one of the many men who have broken Taylor Swift’s heart. Swift was just 19 when she dated the singer and made it very clear in her song, Dear John (which was allegedly written about Mayer). In the song, she talks about how John treated her and even called him out for his “dark, twisted ways.”
Mayer later told his side of the story to Rolling Stone explaining that the song made him feel “really humiliated.” He continued, “I didn’t deserve it. I’m pretty good at taking accountability… It was a really lousy thing for her to do.” Sure, Johnny… whatever you say.
Rashida Jones: 2009
John Mayer and Rashida Jones were spotted out together enough times in 2009 to spark dating rumors. However, it was reported to E! that their relationship was totally platonic. Nevertheless, it caught the media’s attention. Given the singer’s reputation, everyone believed the rumors.
The rumors eventually fizzled out. Jones went on to have a wonderful career in the industry and seems to be having a flourishing personal life as well. In 2018, Jones had her first child with her boyfriend, Ezra Koenig.
Miley Cyrus: 2010
Unless you have been living under a rock for the last 15 years, you definitely know who Miley Cyrus is. According to Glamour, before Miley and Liam Hemsworth found each other, the Hannah Montana actress briefly dated Mayer. Sticking to his usual young type, Miley was a teenager at the time.
Neither Miley nor John confirmed this relationship. Either way, the two seem to be on great terms. In 2015, Mayer tweeted about Cyrus’s new album: “We never get to see ourselves sleeping peacefully next to the ones that we love. I’m totally transfixed by this Miley Cyrus album.”
Kim Kardashian: 2010
Reportedly, back in 2010, Mayer and Kim K were seen partying in NYC together while the reality star was shooting an episode of Keeping Up With the Kardashians. According to Page 6, both Mayer and Kardashian brought friends along to see if there there was any real chemistry between them.
That being said, Mayer wasn’t amused by the hookup rumors and took to Twitter: “I see @kimkardashian at Sirius/XM and say hello like a gentleman and you want to spin a story at my expense? F*** You!” Yikes! Given his reputation as a serial dater, what does he expect people to think?!
Reena Hammer: 2010
The British makeup artist Reena Hammer is the daughter of one of the most respectable makeup artists in the business, Ruby Hammer. Since they hung around some of the same prominent people, Hammer and Mayer met and began dating back in 2010.
The romance ended just as quickly as it started. Apparently, neither Hammer nor Mayer were looking for anything serious at the time. After going their separate ways, Hammer began dating The Tudors’ Jonathan Rhys Meyers. Do you think the two eerily similar names are just a crazy coincidence? Or does she have a type?
Katy Perry: 2012 – 2015
After finalizing her public divorce with Russell Brand, Katy Perry found herself the perfect rebound: John Mayer. Perry admitted to Entertainment Weekly that long before their romance went public, the pair would exchange love letters! How sweet?!
But like all of Mayer’s love stories, this one came to an end too. The pair did spend three years dating on and off but eventually called it quits due to conflicting work schedules and reported trust issues. But you don’t have to worry about Katy Perry. She is now happily married to Orlando Bloom, and the gorgeous couple just welcomed their baby, Daisy Dove.
Meet the Fam Jam
John Clayton Mayer was born on October 16, 1977, in Bridgeport, Connecticut to Margaret and Richard Mayer, a high school principal and middle school teacher, respectively. His parents have an age gap of 19 years, and they didn’t always get along.
The singer confessed that there was a lot of fighting at home, and it forced him to “disappear and create my own world I could believe in.” Mayer is the middle child of three boys; he has an older brother named Carl and a little brother named Ben.
He Is a Designer
Mayer definitely knows how to captivate his audiences just by gently caressing his guitar, but apparently, he has more than just a musical gift. One of these talents goes far beyond the music industry and may not be what you would expect from the songwriter.
Other than winning the Grammys and writing songs that make my heart melt, Mayer is also a fashion designer! That’s right. He took his natural swag and sense of fashion to create his own brand. The singer designs tees, shoes, guitars, and guitar amps!
He Knows Krav Maga!
So, the paparazzi should definitely take note of this… and so should everyone else who plans on ticking off John Mayer. Although he sings calm, beautiful melodies, you don’t want to cross Mayer. This guy knows Krav Maga, Israeli hand-to-hand combat.
This means that there is more to him than the soulful star we see on stage; he is a fighter too! But his desire to expand his horizons and try out all different types of hobbies doesn’t end there. Mayer also wanted to learn a new language and is now fluent in Japanese.
He’s a Philanthropist
Like many other stars, Mayer likes to give back. He has donated some of his fortune to different charities, but there is one organization that means a lot to him. Back in 2002, the singer formed the Back to You fund to support children with matters related to education, health care, and the arts.
He honestly believes children are the future and wants to help them in any way he can. It’s nice to see his soft side which is often overshadowed by his “diva” reputation. Mayer also contributes in other ways such as auctioning off his guitars and other possessions for a hefty price.
Stevie Ray Super Fan
John Mayer is a huge Stevie Ray fan. When he was just 13 years old, Mayer’s love for legendary songwriter Stevie Ray Vaughan began. A neighbor gave him a Vaughan’s cassette, and that was it. Mayer was totally hooked. He was such a major inspiration.
His love runs so deep that the singer went as far as to ink SRV (Vaughan’s initials) on his body. Mayer praised the singer on numerous occasions and has even called himself a “Stevie Ray Vaughan wannabe.” However, The Police is still his favorite band.
He Came Up With “Daughters” in the Shower
You know what they say, you are the most creative in the shower. Well, I don’t know if they say that, but that’s what I heard! Either way, the 2005 Grammy Song of the Year was born in the shower. 27-year-old Mayer was cleaning himself off when the idea for the song Daughters came to him.
I guess a musician’s brain never fully turns off. Inspiration can come from anywhere. Although many songs started off as a shower idea, not many of them go on to win Grammys! To be fair, Mayer is an exceptional talent and can probably write a hit anywhere.
Work Hard, Play Hard
Mayer is known for a lot of things: the women he dated, his dashing good looks, and his partying habits. However, the most notable thing about Mayer is his extraordinary talent, and he won’t let you forget it! He prioritizes his musical career above all else. On one tour, Mayer traveled across the globe playing 188 concerts. If that’s not hard work, I don’t know what is!
Working hard is a trait Mayer acquired at a young age. Before achieving universal fame, Mayer worked at a gas station for $7 an hour. After saving up for 15 months, Mayer was finally able to buy a 1996 Stevie Ray Vaughan signature Stratocaster. We’ve all got to start somewhere.
Back to the Future Inspiration
Remember that classic movie we can’t help but watch every time it’s on TV? Believe it or not, Back to the Future helped inspire Mayer. Obviously, Mayer didn’t join the movie-making side of the industry but watching Michael J. Fox’s guitar performance as Marty McFly is what inspired the singer to pick up the guitar.
It didn’t take long for Mayer to become fixated with the instrument. In fact, his obsession was so bad that it landed him in a psychiatrist office – on more than one occasion. Although Back to the Future helped shape him as a musician, Mayer’s favorite movie is Goodwill Hunting.
His First Lyrics
Since childhood, John Mayer has been buddies with tennis player James Blake. Their friendship dates all the way back the middle school when the kiddos played Nintendo and tennis together after school.
When he was in high school, 17-year-old John Mayer was stricken with cardiac dysrhythmia. He needed to spend a week at the hospital. Bored, with a lot of free time on his hands, Mayer used this experience to write his first song. The singer was admitted as a patient and discharged as a songwriter. Way to make the best of a bad situation.
He Gets Rejected
It must be nice to be one of the most good-looking guitarists on the planet, and that angelic voice doesn’t hurt either. It’s really no surprise that he has an endless list of ladies; everyone wants a piece of John Mayer. Well… not everyone. Even a heartthrob like John Mayer gets rejected every once in a while.
According to the singer, he once went up to a woman and gave her his number, only to get a soul-crushing response. Apparently, she looked at the number, looked at him, and said: “I probably won’t use it.” Ouch!
His Body Is a Wonderland
With so many famous exes, it’s only natural to wonder who Mayer is singing about. People have speculated about his hit Your Body Is a Wonderland for years. I mean, there are so many people he could have been talking about, like Jennifer Love Hewitt. But the actress denied that the song was written about her.
Mayer admitted that he isn’t very happy with the song’s legacy, mostly because he gets constant ridicule over it. Apparently, drunk men love to yell the lyrics at the singer while he’s innocently walking down the street.
A Woman’s Scent
Among his many talents, Mayer has a rather peculiar one: He can accurately guess which perfume a woman is wearing. In a 2012 Rolling Stone interview, a group of girls walked by and Mayer bragged about how good he is with scents.
He then turned toward one woman and asked if she was wearing a perfume called Child. She was stunned and replied, “I am. Well done.” That is a pretty impressive skill. But how many perfumes can he possibly know? There must be a few that he hasn’t had a chance to smell yet!
Never on the Day You Leave by John Mayer includes the lyrics, “She’ll fight for you like hell, then force herself to like some other man.” But there is a heartbreaking history to those words. Like many songs, this was written after a breakup.
When Mayer split with an unidentified ex, he came up with the tune, and explained that this line in particular is extremely painful. The singer admitted that it’s difficult for him to perform the song live and he’s cried several times while recording it. I wonder which girl broke this dreamboat’s heart.
The Way to His Heart
Mayer revealed that he has a thing for good grammar. He confessed that the best way to win his heart is “good spelling and good grammar, good punctuation, capitalize only where you are supposed to capitalize, it’s done.”
I feel the same way! We writers with our standards. However, this attraction came with a strange, dark side when it came to his infamous relationship with Jessica Simpson. Simpson confessed that he would take pictures and study her body, leaving the singer “worried he was keeping souvenirs before dumping again.”
Fame Intensified His Anxiety
Mayer has suffered from severe panic attacks since childhood. The more famous he got, the worse they got. He was overly anxious to get praise and admiration for his music and songwriting talents.
This caused him to worry constantly. He was so scared that his fame would run out. Any critical comments about his performances and getting called a “womanizer” intensifies his anxiety. Wow, he needs to find a way to relax. Perhaps meditation or a spa day?
Severe Panic Attacks
In 2012, Mayer told Rolling Stone that his panic attacks would get so bad, that he worried he would have to check himself into a mental institution. Which of course, added to the anxiety. Mental health is very real, and it’s comforting when celebrities talk openly about it.
Mayer’s friend Joe Beleznay explained the extent of the singer’s panic breakdowns. He said that Mayer’s brain “works at such speed” that he would “second-guess his sanity at times.” No wonder why so many creative geniuses suffer from anxiety.
Sing to Me, John
Mayer admitted that when he was first getting famous, he used his music to get women into bed. And who could blame him? It’s really not all that surprising for someone to use their fame to get girls. It probably would have worked on me. Still, it’s a bit disturbing and about to get even creepier…
Mayer said that he does not play music while he is doing the deed, but he confessed that many girls had “asked me to sing… in the run-up to it.” Well, there is an image I want to get out of my head.
His Worst Nightmare
Speaking of girls in bed, there might be a reason Mayer fears sleeping alone. Apparently, the singer suffers from terrible nightmares – with a strange twist. In these dreams, Mayer is about to do it with someone, but then the paparazzi burst in and make him unable to perform.
I know many people wouldn’t consider this a scary nightmare, but I can sort of relate. When I started Keto (Ketogenic diet), I would get recurring nightmares when I ate a potato chip! I guess it’s not quite the same, but we all have our fears.
Whose Body Is a Wonderland?
Mayer’s song Your Body Is a Wonderland was a smash hit when it came out in 2002. Everyone speculated about whom it was written, but the most popular theory was that it was written about Jennifer Love Hewitt, whom he was dating around the time it came out. Nothing was confirmed or denied… until 2012.
Mayer finally confessed whom the song was about in a 2012 interview. He said that he wrote it about a girl he fell in love with back when he was 14. He didn’t reveal her name, but he did say, “This woman is precious. She can vouch for me not as a celebrity. She carries with her information of this 14-year-old boy she knew.”
Comedian Kumail Nanjiani told an incriminating story about John Mayer. Apparently, the singer considers himself a stand-up comedian, and on one occasion he prevented Nanikani from going on stage so he could perform a five-minute stint for the audience.
Well, as it turned out, five minutes turned to 20, and Mayer simply refused to leave. When Nanjoani finally got to perform, as he was supposed to, Mayer returned the favor by mocking him. How rude! He called Nanjiana “Kabul” and said, “he looked like a brown guy but sounded like a white guy.”
Discussing His Struggles
Mayer has been honest about a lot of his struggles. Aside from his anxiety, Mayer opened up about his alcohol issues and finding emotional stability. Although he was never an alcoholic, he did say that he never felt like he could drink the right amount.
He went on to explained that whenever he drank, he didn’t feel like he was “succeeding at life.” Nowadays, he has almost stopped drinking and called it a “con.” Good for you, John! Keep up the healthy lifestyle.
An Old Lover
It’s been over a decade since Taylor Swift and John Mayer’s relationship. After Taylor wrote a song about John, people assumed that the couple didn’t end on the greatest terms. But in more recent years, Mayer admitted that he really likes Swift’s song Lover.
However, he has one teeny issue with it. His problem is with the line about keeping “the Christmas lights up ‘til January.” Mayer said that’s “insane” because “everyone keeps their Christmas light up until January.” It’s March and I just took mine down… but that’s because I was too lazy before.
He Has a Legendary Mentor
John Mayer is one of the few people on the planet who can say that he has a bona fide rock god as a mentor: music icon Eric Clapton. The singing legend took an interest in Mayer’s talent and in 2006, he invited him to a 10-day writing workshop. According to Clapton, he spent a lot of time snapping Mayer out of his habit of being a “bedroom guitar player.”
Clapton isn’t afraid to give his pupil some tough love. Even though the seasoned guitarist said that Mayer has immense talent, he also called the singer out in an interview for being “a prime saboteur” of himself. Sounds about right.