The 17 Women Of John Mayer's Little Black Book

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!

16 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."

15 Holly Williams, 2002

14 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?

13 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.

12 Cameron Diaz, 2007

11 Mandy Moore, 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".

10 Minka Kelly - 2007-2008

9 Jennifer Aniston - 2008


8 Colbie Caillat, 2008


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 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.

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?

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.”

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.

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.

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...

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!


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The 17 Women Of John Mayer's Little Black Book