Scandalous Details About John Mayer's Personal Life

Singer-songwriter John Mayer has won seven Grammy Awards (nominated a total of 19 times), scored three number-one albums on the Billboard 200, and earned the adulation of millions across the globe with his smooth-as-honey voice, brooding pin-up looks, and sensitive soft-rock sound.

But the Bridgeport native has often appeared to go out of his way to self-sabotage his phenomenally successful career. Barely a month went by at the peak of his success without an interview that was either problematic, offensive, or a severe case of TMI. "I started to invent my own grenade," he told The New York Times in 2017. "What I did was probably semiconsciously just reboot it — control, alt, delete. [...] It was cat and mouse. And the mouse lost."

From objectifying scream queens and degrading pop idols to unexpected kisses and unhealthy addictions, here's a look at 14 times Mayer's musical talents — and with no one to blame but himself — were overshadowed by his tabloid-friendly personal life.

John Mayer was still seen as one of the singer-songwriter scene's nice guys in 2006. But that all changed in October of that year when the Grammy winner took to the stage at Los Angeles' The Laugh Factory for an unexpected stand-up set.

The former Berklee College of Music student proved that he should stick to his day job, after making an ill-advised joke about his brief 2002 relationship with Jennifer Love Hewitt. Mayer told the audience that he and the "I Know What You Did Last Summer" actor had never made it to the bedroom because of a case of food poisoning. As well as going down like a lead balloon, the quip was also criticized for objectifying his former squeeze.

Mayer, who has since quashed rumors that his signature hit "Your Body Is a Wonderland" was written about Hewitt, later apologized for his misjudged sense of humor. He told Us Weekly, "It really was me making fun of myself" before declaring himself as a wimp. 

It seems fair to say that John Mayer doesn't always learn from his mistakes. Four years after he was accused of objectifying Jennifer Love Hewitt live on stage, the troubadour ended up speaking a little too candidly about another former celebrity girlfriend, Jessica Simpson.

Speaking to Playboy in 2010, a foul-mouther Mayer painted a picture of the "I Wanna Love You Forever" singer that was at odds with her girl-next-door persona. The singer-songwriter, who dated Simpson for nine months in the mid-'00s, remarked, "That girl is like crack cocaine to me. Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm."

Seemingly without any kind of filter, Mayer continued his charm offensive, "Have you ever been with a girl who made you want to quit the rest of your life? Did you ever say, 'I want to quit my life and just f***in' snort you? If you charged me $10,000 to f*** you, I would start selling all my s*** just to keep f***ing you.'" Understandably, Simpson was left mortified by her ex-boyfriend's comments, writing in her 2020 autobiography "Open Book" (via In Touch Weekly), "He talked about me by name in the most degrading terms."

As well as addressing John Mayer's degrading comments about her sex drive, Jessica Simpson also used her autobiography "Open Book" as an opportunity to delve further into their difficult relationship. And as you'd expect, the singer-songwriter didn't come off particularly well.

Simpson, who dated Mayer for nine months in the mid-2000s, revealed that she turned to drinking to deal with the anxiety she suffered as a result of the singer-songwriter's behavior. The big-voiced pop idol wrote (via Insider), "I constantly worried that I wasn't smart enough for him. I was so afraid of disappointing him that I couldn't even text him without having someone check my grammar and spelling."

She also disclosed that Mayer repeatedly played with her emotions by constantly breaking up and then getting back together with her. In fact, the "Heartbreak Warfare" singer called it a day on no fewer than nine occasions, and always via email. "He would tell me that my true self is so much greater than the person I was settling on being," explained Simpson. "Like there was some great woman inside me waiting to come out, and I had to hurry up and find her because he wanted to love that woman, not me."

Jennifer Aniston found herself apparently unable to resist John Mayer's charms when she began dating him in 2008. But the "Friends" favorite soon found herself on the ever-growing list of celebrities done wrong by the singer-songwriter, too.

Mayer went out of his way to make it clear that he was the dumper and not the dumpee, following their first split just months after they met at an Academy Awards bash. "I'm the a**hole," the "No Such Thing" hitmaker told reporters outside a Big Apple gym, before dramatically adding, "I burned the American flag. I basically murdered an ideal."

The couple ended up getting back together but split for good in 2009. And once again, Mayer wanted everyone to know that he'd been the party to call things off. In his controversial interview with Playboy a year later, he revealed that an encounter with a woman named Dimples in Las Vegas helped him to see that "The Morning Show" star wasn't the one. Referring to the eight-year age gap between them, Mayer added, "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 the fact that I need to be 32."

Not content with publicly declaring that he'd been the instigator of his break-up with Jennifer Aniston, John Mayer then outed the "Friends" star as a technological Luddite. In his candid 2010 interview with Playboy, the "Gravity" singer denied the rumors that his addiction to Twitter had been the sole cause of their split, but did reveal that their differing attitudes to the online world had played a part.

In a rather blunt and deeply patronizing manner, Mayer said, "If Jennifer Aniston knows how to use BitTorrent, I'll eat my f***ing shoe ... 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.'"

Aniston had previously insisted she harbored no ill feelings toward her ex, telling Vogue in 2008, "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." The actor even went on to describe Mayer as a "wonderful guy" before adding that she still cares for him, too. And despite calling her out for her lack of technological nous, the pair are reportedly still pals.

John Mayer once again proved to be a reporter's dream in 2010 when he gave an interview to Rolling Stone which pretty much redefined the term 'oversharing.' The "Waiting on the World to Change" singer made various eye-catching claims about his masturbatory habits and attitude to fame. But it was his comments about female genitalia that grabbed most of the headlines.

Discussing the hardships of finding a long-term girlfriend, Mayer said, "Do you think it's going to take meeting someone who I admire more than I admire myself? But isn't it also about a beautiful vagina? ... Like, you need to have them be able to go toe-to-toe with you intellectually. But don't they also have to have a vagina you could pitch a tent on and just camp out on for, like, a weekend?"

Mayer, who added that he was essentially looking for "The Joshua Tree of vaginas," also disclosed that he was currently only interested in sleeping with girls that he'd already slept with, adding, "Because I can't fathom explaining myself to somebody who can't believe I'd be interested in them, and they're going, 'But you're John Mayer!' So I'm going backwards to move forward. I'm too freaked out to meet anybody else."

Controversial gossip blogger Perez Hilton found himself on the receiving end of John Mayer's insatiable appetite for drama in the '00s when he was kissed in public by the multiple Grammy Award winner. But the smooch wasn't in any way, shape, or form a romantic one. It was simply intended as an act of one-upmanship.

In his famously outspoken chat with Rolling Stone in 2010, Mayer revealed the circumstances behind the unlikely encounter, unfortunately, while also using a homophobic slur: "I remember seeing Perez Hilton flitting about this club and acting as though he had just invented homosexuality. All of a sudden I thought, I can out-gay this guy right now. I grabbed him and gave him the dirtiest, tongue-iest kiss I have ever put on anybody — almost as if I hated f**s."

Hilton himself addressed the incident in his 2020 memoir, "TMI: My Life in Scandal," alleging that Mayer also revealed a fascination with gay porn during their encounter at a Chelsea club. Furthermore, the writer claimed that Jessica Simpson, the singer-songwriter's girlfriend at the time, "... didn't seem to know whether she was incredibly embarrassed or really turned on."

The most eyebrow-raising relationship in John Mayer's exhausting romantic past is undoubtedly his brief one with Taylor Swift. The pair went from musical collaborators to lovers after duetting with each other on the track "Half of My Heart." But controversially, the troubadour was 32 years old at the time, 13 years the country star's senior. This age gap was  famously addressed in Swift's 2010 break-up song "Dear John."

In the heartfelt ballad, which appeared on her second studio effort Speak Now, Swift sings (via Genius), "Dear John, I see it all now, it was wrong/Don't you think 19's too young/To be played by your dark, twisted games/When I loved you so?" As a result, the army of Swifties made the former object of her affections their number one enemy. But while on her exhaustive "Eras" tour in the summer of 2023, the singer asked fans to drop their vendetta.

"I'm 33 years old," Swift said on stage (via Vulture). "I don't care about anything that happened to me when I was 19, except the songs I wrote ... So, what I'm trying to tell you is that I'm not putting this album out so that you should go and feel the need to defend me on the internet against someone you think I might have written the song about 14 million years ago."

John Mayer, a man who's regularly disclosed the most intimate details about his personal relationships, was accused of being a hypocrite in 2012 when he claimed that Taylor Swift shouldn't have written a song about him. He told Rolling Stone he was left feeling humiliated on first hearing his ex's breakup song, "Dear John."

"It made me feel terrible," Mayer said, seemingly without any sense of self-awareness. "Because I 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. I mean, how would you feel if, at the lowest you've ever been, someone kicked you even lower? I will say as a songwriter that I think it's kind of cheap songwriting."

Any shred of sympathy completely disappeared, however, just a year later when Mayer released his own song referencing Swift. "Paper Doll" alluded to several of her songs including "Dear John" and "22," the latter in a particularly scathing way. He sang (via Genius), "You're like 22 girls in one/And none of them know what they're running from/I'll look back and regret/How I ignored when they said/Run as fast as you can."

In his all-too-revealing interview with Playboy, John Mayer freely confessed to being addicted to porn. In fact, the "Bigger Than My Body" singer was so enamored with the form of adult entertainment that his ultimate career goal was to write it.

The singer-songwriter explained that the proliferation of media platforms had only exacerbated his fondness for "self-soothing," as he described it: "The Internet, DVR, Netflix, Twitter — all these things are moments in time throughout your day when you're able to soothe yourself. We have an autonomy of comfort and pleasure ... You wake up in the morning, open a thumbnail page, and it leads to a Pandora's box of visuals. There have probably been days when I saw 300 vaginas before I got out of bed."

Mayer also admitted that his habit had ultimately ruined his sex life, adding, "Absolutely, because during sex, I'm just going to run a filmstrip. I'm still masturbating. That's what you do when you're 30, 31, 32. This is my problem now: Rather than meet somebody new, I would rather go home and replay the amazing experiences I've already had."

As well as comparing his daily struggles — whatever they are — to those of Black America in his 2010 interview with Playboy, John Mayer also made some highly problematic comments regarding race and his sexuality.

The "Daughters" singer compared his manhood to white supremacist David Duke before revealing that he was going to try and become more open-minded when it came to dating women of color. And there were a few, in particular, that he found himself attracted to including "21 Jump Street" actor Holly Robinson Peete, "The Fresh Prince of Bel-Air" star Karyn Parsons and "Scandal" favorite Kerry Washington. Considering what followed, however, it's unlikely that the latter would ever give him the time of day.

Referring to Washington, Mayer suddenly said out of nowhere, "She's superhot, and she's also white-girl crazy. Kerry Washington would break your heart like a white girl. Just all of a sudden she'd be like, 'Yeah, I sucked his d***. Whatever.' And you'd be like, 'What? We weren't talking about that.'" Deservedly, the troubadour received a lot of flak for his comments, with "The Race Card: How Bluffing About Bias Makes Race Relations Worse" author Richard T. Ford telling Us Weekly that such "tongue-in-cheek racism satirizes racial stereotypes and but also sort of traffics in them. Sarah Silverman does post racist very adroitly — she's both hilarious and thought-provoking. Mayer does it badly — he's offensive and tiresome."

Two years after making degrading comments about ex-girlfriend Jessica Simpson and her sex drive, John Mayer made another startling revelation: everything he said about the "I Think I'm In Love With You" singer had been exaggerated.

During a 2012 appearance on NPR's "All Things Considered," the singer-songwriter admitted that he brought Simpson's name into disrepute simply because he couldn't think of anything else to make him sound interesting. He said (via TODAY), "I was going through a time in my life where I didn't really want to share what was going on, but I didn't want to be boring."

Mayer, who was later called out by Simpson herself for his remarks in her 2020 memoir "Open Book," went on to add, "When you're just open, but not honest, then you start free-associating garbage. It doesn't mean I can go back and scrub it out, but I understand it now."

To the surprise of no one, John Mayer admitted during an Instagram Live show in 2018 that he took full advantage of his sex symbol status back in his heyday. The "Love on the Weekend" singer made the confession while acknowledging that he's no longer as lusted after, now that he's in his 40s.

Mayer said (via People), "I actually find that people not being into me brings a real level of reality into my life. Whereas when I was in my early 20s, where I couldn't really miss, I really kind of abused that. That's now out of the question." The Grammy Award winner then discussed a recent encounter with a girl who freely admitted that she wouldn't use the phone number he'd given her. "I actually think it's awesome too because I would have ruined her," the star added during the chat with Larry David's daughter (and former Pete Davison squeeze) Cazzie David.

Of course, a Mayer chat wouldn't be a Mayer chat without at least some form of humblebrag. The Billboard chart-topper still let it be known that he could "have sex with somebody at any moment," going on to add, "But being a famous man is somewhat similar to being a beautiful woman: there is access, there's very seldom any desire. The older I get the less desirous I am of unsheathing new body parts."

In 2020, Scheana Shay of "Vanderpump Rules" fame made tabloid headlines for a conversation on her podcast "Flashbacks" in which she discussed her brief dalliance with John Mayer. According to the reality TV star, there were three people in their relationship.

Yes, according to Shay, she and Mayer entered into a throuple with Stacie Adams, her-then roommate, back in 2008. The arrangement apparently came about after they partied together at the Grand Havana Room where the reality TV star worked. But over time, Shay began to grow jealous of Mayer's preference for Adams. She recalled (via People), "I was like, 'Wait, I brought you into this, like, and now you're getting more attention than I'm getting, like what's up with that?' And then even after [he] and I stopped talking, they continued talking, and there were like a lot of things — like [she] and I had like a year of just awkward friendship falling out ..."

To add insult to injury, Shay also ended up losing her position at the establishment for the crime of fraternizing with guests. But this proved to be a blessing in disguise. She landed a job at Lisa Vanderpump's Villa Blanca eatery and was subsequently invited to appear on her eponymous show. Shay also managed to patch things up with Adams and even asked her to be a bridesmaid at her first wedding.