Given who we are talking about here, it would likely be easier to compile a list of women John Mayer has not slept with, than those with whom he has. Nevertheless, I shall try. And while I am sure there are plenty of women we do not know about, on this list there is nary an unfamiliar (read: non-celebrity) woman he’s been with. It should be testament enough to how many notches are on John Mayer’s belt that his conquests are all over the internet.
Many articles refer to the womanizing crooner’s hookups as his “victims”, often speculating as to who would be his next. Nowadays it seems as if his love life is not as in the spotlight as it was in recent years, but no worry. I have 17 out of his God-knows-how-many lovers right here, and you can decide for yourself if they are victims or if they are lucky to have been with him.
I am sure John Mayer has his good qualities too, but personally I don’t get the appeal (especially since these starlets could pretty much have any man they want!). Between what I have learned of his relationships, and the fact that his face is an exact replica of one of my own awful exes, my sympathy for Mayer the Player is limited, if existent at all.
So here they are. I see no other fair way to list these women than in chronological order, beginning in 2002 with the lovely Jennifer Love Hewitt. Here goes!
17. Jennifer Love Hewitt, 2002
Though we have not seen much of her in the Hollywood scene lately, it is rumored that she was, in fact, the muse for John’s hit song “Your Body is a Wonderland”. Well, it is true that J. Love has it going on with that teensy-weensy waist and long princess hair. So I could see that being true. The song was released in 2002, the same year that the two dated, though Jennifer denies the song being about her, saying to Entertainment Weekly that, “My body is far from a wonderland. My body is more like a pawn shop. 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.”
The relationship between John and Jen was intense but brief. John admitted to being in love with her, but calls the time with her a “strange little detour that I took for a minute.” An interesting way to describe it for sure, but it seems as though these two parted amicably, and even if not, it has been 14 years now so hopefully all is well.
16. Holly Williams, 2002
Holly Williams is famous for being Hank Williams, Jr.’s daughter, but not much else. She did make headlines when she was linked to rocker John Mayer, though. And she is a singer/songwriter, but I mean, who isn’t? Several sources say the two definitely briefly hooked up (implying more than once, as I read it), so I don’t think there is any question there. But she deserves a spot on this list not only for her maybe-but-probably hook up with John, but because she did, in fact, date the man. A victim of his boyish charms, Holly admits, “I fell in love with him for a couple of weeks like every other girl who sees him play guitar.” Yeah, pretty much. Hopefully, for her sake, it was fun while it lasted!
15. Vanessa Carlton, 2002-2003
2002 sure did seem to be John Mayer’s year! After Holly Williams and Jennifer Love Hewitt, he entered into a slightly longer relationship with musician Vanessa Carlton of “1000 Miles” fame. While they were simultaneously climbing the charts with their respective hit singles, they dated for about a year. It was rumored that many of her song lyrics were actually about him; after all, she was an angsty teen pop star who had been jilted by the bad-boy heartbreaker. Makes for good lyrics, no?
Apparently, their relationship over that year was of the on-again-off-again type, but ultimately it seems that Vanessa was the one who ended up hurt. When she came out as bisexual many years later in 2010, many jokes were made that John had turned her gay. Now she is happily married and a mom, and I am sure that bad boy is nothing but a distant memory (that is, until people like me dredge it up- sorry, Vanessa!).
14. Jessica Simpson – 2006-2007
John and Jess dated “seriously” over the course of 2006 and 2007, but their controversial breakup was horrendous; possibly the worst in his repertoire of countless relationships. This is because during a Playboy interview, he compared her to “crack cocaine” and wanted to “snort her”, and divulged intimate details of their sex life. He even famously called her “sexual napalm”. That is a super douche move by anyone’s standards, and if I were Jess, I would not ever forgive him, either. How embarrassing! Though he later apologized, some things are just too little, too late. At least he referred to himself as a jerk. That’s something.
But in the end, it was Jess who won the support of the public when she went on Oprah (who has millions of viewers) and was visibly upset, saying she did not want people to know how she was in bed. Well no, I would think not, since she very publicly saved herself for marriage (to Nick Lachey in 2002; they divorced in 2006). Luckily she has since found second husband Eric Johnson, and become the mommy to two little ones. So good riddance, John Mayer!
13. Cameron Diaz, 2007
While filming What Happens in Vegas in New York in 2007, Cameron Diaz was also up to no good with John Mayer. Having just ended his relationship with Jessica Simpson, the playboy spent an intimate weekend with yet another blonde bombshell, this time Hollywood sweetheart Cameron Diaz, who herself had just ended a relationship as well, with Justin Timberlake. How lucky they could find comfort in each other’s arms (gag). The two made no secret of their PDA, and various sources labeled them as being “all over each other” and “super flirty”. But it lasted longer than just one weekend, as both prior to and after that weekend they were spotted dining out and having drinks at different locations. They were confirmed by a source close to John as definitely dating. Previously, they had hung out together with mutual friends in a group, and that, apparently, led to much more.
12. Mandy Moore, 2007
Also after the controversial breakup with Jessica Simpson in 2007, John occupied himself with fellow singer Mandy Moore. They were romantically linked and several media outlets claim that they were also lovers, but Mandy denies it all. They do seem quite opposite; for her part, she says she has only been drunk about 4 times in her life. Mayer, on the other hand, has had lists published online of his “douchiest” quotes, most of which could only have been said while under the influence. Take, for example, what he had to say about his short-lived maybe-romance with the darling, innocent-seeming Mandy Moore: “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? The Joshua Tree of vaginas? … I’ll be happy when I close out this life-partner thing. Think of how much mental capacity I’m using to meet the right person so I can stop giving a f— about it.” (Rolling Stone, 2010). For Mandy’s sake I hope nothing really did happen between them, but alas, she is on every list there is of his “conquests”.
11. Ricki Lake, 2007
John Mayer had an unabashed (albeit strange) crush on Ricki Lake, who many from my generation remember as the cutesy, quirky talk show host turned judgy, breastfeeding maniac mom. Or something like that. But in 2007, the two talked and exchanged phone numbers at a party in Manhattan, and after that, well, you know, they must have had a torrid affair. The tabloids will say anything of course, so let’s stick to what we know: he admits to a longstanding crush (two years!) on the older woman, they exchanged digits and then texted all night, and they were “spotted together”.
Ok, an affair sounds possible but sketchy (and womanizer though he may be, Ricki Lake? Really? Seems odd, but hey, to each their own). This most fleeting of romances seems, in all likelihood, to be more sweet than serious. But if he got her number, which he most definitely did, then she is in his figurative Little Black Book. Besides, who knows what happened after all that late-night texting (and presumably, since it was the night of a Christmas party, drinking)? Either way, it was reported that she lost his number. Ouch! The player gets played!
10. Minka Kelly – 2007-2008
Even the drop-dead gorgeous Minka Kelly could not hold on to this player for long. Rumor has it that he was not “ready” for a serious relationship, and that before the news of their breakup went public, he called her to tell her he was in love with Jennifer Aniston. Well I mean, really who isn’t? But that is no excuse. This guy is something else, and I think he did poor Minka a favor. That girl could have any man she wants (can you tell I have a girl crush on her?)! The Friday Night Lights actress also quickly moved on though, to New York Yankees shortstop Derek Jeter. So all’s well that ends well. And it did- the two actually remained close, having breakfast together just days after the split, and when she showed her support for him at a concert that December, as well as accompanying him to the show’s after-party. She told a source that they had broken up and she did not want to tell anyone, but that they were still friends. Hey, if you can be, that is way better than the alternative, so good for them.
9. Jennifer Aniston – 2008
And then we have the beloved America’s Sweetheart, Jennifer Aniston (another one I am protective over!). John again berated himself for losing yet another great girl; I believe “a**hole” was the adjective he used, and quite appropriately. He told one media outlet that he has never really gotten over her, that their split was the “worst time” of his life, and that he had “murdered an ideal”. Wow, that sounds intense. The couple first got together in April of 2008 after spending 5 sexy days together in Miami. They would go on to split up twice, but in some twisted revelation, John revealed that then, “All I want to do now is f**** the girls I’ve already f****ed, because I can’t fathom explaining myself to somebody who can’t believe I’d be interested in them,” he says about his frustration with dating non-celebrities. He went through a phase of only wanting the women he’d already had… and dumped. Hopefully he got past that fast, and hopefully if not, those ladies are classy enough to give him the finger and nothing else.
8. Colbie Caillat, 2008
John and the sweet-voiced Colbie had been in discussions to collaborate on some music when they were caught in a kiss! Luckily for us, the paparazzi caught it on camera. Sounds like they were making something other than music, if you know what I’m saying! Before her hit song “Bubbly”, Colbie Caillat was an American Idol reject (she didn’t even make it in front of Simon!) that would wind up being John Mayer’s tourmate… and more. It is rumored that the two dated, however briefly, and he invited her on his 2008 summer tour. Colbie calls John a friend (as she talks about what it’s like to date friends, hmm…), and one of her musical icons. The two flirted, played pranks on each other, and seemed to have a playful relationship. Given John’s womanizing ways and Colbie’s being starstruck over him (not to mention they were on tour together for a whole summer), I’d say there’s a high probability that those “rumors” of the two dating were not really rumors, at all.
7. Scheana Marie, 2009
In case you don’t know (I didn’t), Scheana Marie is a cocktail waitress/model/Vanderpump Rules reality star who met John at a lounge in Beverly Hills. However, before things could get too serious, she made the mistake of going too public with the details of their relationship, spilling things like, “I love his personality… he’s funny…He can be, like, a dork,” to YoungHollywood.com. But she became flustered when asked about their sexual relationship, and said she “just wants to make sure John knows that she really cares about him and is not using this media attention to further her career. Of course, she’s not. She did make clear, however, that he was not her boyfriend. They had dated for one month.
Pissed, John broke all ties with her and wanted nothing to do with her, though that is a bit hypocritical given some of his, um, graphic interviews on the topic of his love conquests (ahem, Jessica Simpson). Nevertheless, that is what happened with the woman who is arguably the least famous person on this list. Sad, as she had hoped for him to be her birthday date the following week. Sigh.
6. Miley Cyrus, 2009
Little Miss Miley had a schoolgirl crush on the much-older (by 15 years!) John Mayer when she was in high school, but when she was 18, she and her crush were caught kissing backstage at the Grammy’s! Now the question is, is there more to the story? Well, obviously! You don’t just run into someone and start making out with them. The story goes, apparently, that she had spent that weekend chasing after him “like a puppy dog” at various Grammy parties, and that the kiss began after she started rubbing his back. John did not seem to mind any of this, or when she grabbed his butt. He even returned some of the affection, according to those present at the parties, by touching her neck and face. He definitely did not mind the attention, and as we know, Miley can be headstrong and goes after what she wants, so who knows what else that kiss led to when no one else was around?
Interestingly, years later Miley would engage in a kiss on stage at her Bangerz concert in 2014, with none other than John’s most well-known lover, Katy Perry. Katy said publicly she was “grossed out” by Miley’s slip of the tongue, to which the feisty singer replied that Katy should be more worried about where John’s tongue had been, since at the time John and Katy were still an item. Touche.
5. Taylor Swift, 2009-2010
The breakup between Taylor Swift and John Mayer (who are both serial daters known to write songs about the ends of their relationships) led them both to do just that. Or at least, allegedly so. Taylor’s “Dear John” and John’s “Paper Doll” were supposedly about each other. Well, at least they have something in common! However, at this point John was in his own so-called “ego recovery”, and was all about taking responsibility for his past words and actions with girlfriends. In an interview with Rolling Stone magazine, he said of her song lyrics that, “It made me feel terrible… 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.”
He also called it “cheap” songwriting, though acknowledged that he would never have the star status of this particular ex (I would say he will never have the star status of many of his exes!). At the very least, he is learning humility. He said that after the breakup, he was unaware of the level of Taylor’s heartbreak until he heard her song. “I never got an e-mail. I never got a phone call,” he said. “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?” Poor John.
4. Ke$ha, 2010
Perez Hilton pretty much sums this “relationship” up: “This is the kind of girl that John Mayer belongs with – someone who dresses from a dumpster and is drunk enough to be attracted to a plastic bag. Which is good because when we think of John, that is the first image that comes to mind. A gigantic D-Bag!” Well said, dude. The two boisterous musicians engaged in a so-called “twittermance” that one source said was them “jerking each other off”- basically, it was sexually- charged banter the equivalent of olden-day flirting. But after one particularly graphic tweet from John, Kesha responded by telling him to stop being a little b**** with his chit-chat and show her his d***. Wow. Classy.
It would not be a stretch of the imagination that these two actually did hook up. After all, it was John who was crushing on the “Tik Tok” singer first, and he apparently won her over, proven by her statement: “I really want him. I met him, like, years ago when we were both nobodies and he was really nice. I haven’t pashed him… yet. I hear he’s incredibly well endowed. I want to check that goody bag for myself!” Key word: yet. I hear determination (and drunkenness soon followed by bad decision-making) in her words. By the way, “pash” means “kiss” in Australia.
3. Kim Kardashian, 2010
I have to admit this one is a bit of a shocker to me, though I guess it shouldn’t be. We all know John is a man wh$%e, but Kim K. is not exactly virginal, herself. In 2010, these two promiscuous stars hung out with some people in New York City, specifically to see if there was any chemistry between them. There must have been, because after that, they spent a few nights hitting the town, sans any friends. Alone. New York City + Kim Kardashian + Player Mayer = Trouble, for sure.
A source close to Kim said that while they were nothing serious “yet”, she thinks John is a “really cool guy”. She was said to be “on the prowl” at the time, and has a penchant for dating bad boys. And of course, John would do any woman who would have him, so there you have it. They went on a few dates and hit it off, but it must never have been too serious because if it had, we would be reading more about the breakup than the hookup. I just can’t help thinking, though, that these two could have tried a little harder; it seems to me that they could be a match made in heaven.
2. Renee Zellweger, 2011
Well, Bridget Jones and her diary meets John Mayer and his Little Black Book. A cute couple, no? Both Renee and John have been known to make their way through the Hollywood dating world, so eventually they would hook up or date. It was just inevitable, really. But some sources back in 2011 got a little snarky and said that Renee was into taking Jennifer Aniston’s leftovers, since she also dated Bradley Cooper, another Aniston ex. I mean there are only so many A-Listers to pick from, so…
Anyway, there was a lot of secrecy and rumors surrounding the duo, as John and Renee kept their whatever-it-was pretty quiet, though they were spotted out together several times in both New York and Los Angeles. But it was not too serious, at least not for Renee, who was “looking for a good time with a hot guy”, according to sheknows.com. You go, girl!
1. Katy Perry, 2012-2014
Katy Perry is perhaps John’s longest and most famous relationship, as they were together for years. It was John that ended things, reportedly due to her partying and busy lifestyle, something you would think he would know a thing or two about. Maybe he had just been with one woman too long (much longer than any of the others!). Who knows? But in the end, she moved on with Orlando Bloom, and it is said that her ex was so heartbroken over “losing” her that he went to great lengths to get her back. He even proposed to her over the phone- while they were broken up! But all was not lost despite the man’s groveling for another chance. In fact, just last year the exes attended a wedding together and even held hands, sparking rumors of a reunion. They both denied it, and a source close to the couple had this to say, “They are exes that everyone can aspire to be like because they are mature and kind and gracious to each other. They were happy to see each other and spend time together at the wedding, but they are not a couple.” It may have ended roughly, but it looks like clear skies ahead for these ex-lovers and current friends!