20 Photos Of John Mayer With His Too-Gorgeous-For-Him Girlfriends

John Mayer certainly has the ability to irk people. The candid way he talks about his dramatic love-life and women, in general, tends to make people royally pissed. He's got an attitude. But at least the talented musician doesn't mislead. Anyone who's read anything about him knows precisely what he's about. And yet, certain famous women keep hoping that they'll be the one to tame the beast. Newsflash! ...They won't... Only he can do that. And, by the sounds of it, he doesn't want to. Mayer even told Andy Cohen that he's more than comfortable being a serial dater, which he absolutely is. After all, he's been tied to many women aside from the ones on this list. The only thing is, he's not with them long enough for the paparazzi to snap a picture. Whether you're a fan of his or not, we can all agree on the fact that most of the women he's been with seem FAR too good for him. Nonetheless, he keeps gaining their attention. Without further ado, here are 20 photos of John Mayer with his too-gorgeous-for-him girlfriends.

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20 Two Celebs With Quite The Dating Track-Record... To Say The LEAST...

Daily Mail and Pinterest

Okay, so Taylor Swift fans REALLY hate John Mayer, but she's basically his female equivalent. Taylor may act with more grace than John, but she trashes every famous boy she's ever been with (which is a lot). She just sings about them instead of gossiping to the press. So, it wasn't THAT surprising when the two of them got together in 2009. And it definitely wasn't surprising when they both called it quits. At least they performed a heck of a duet together!

19 We're Shocked By What Actually Happened With Jessica Simpson In This Moment

Daily Mail

They broke-up. Yep, the paparazzi actually caught the precise moment that John broke things off with the starlet back in 2007. They were on vacation in Cabo and managed to grab a bit of attention while they argued on their hotel balcony. The optics of these photos don't look so good for John, but hey, that's really not anything new.

18 John Mayer Appreciates The Lights Of Friday Night With Little Minka

Daily Mail

The Friday Night Lights star was definitely too good to be hanging with John Mayer. After she moved on from super-athlete Derek Jeter, Minka Kelly spent quite a bit of time with the controversial musician. Here we can see their chemistry was straight fire while they attended a basketball game. Unfortunately, their relationship didn't last too much longer after this moment.

17 John And Katy Make Their Getaway

Daily Mail

Before Orlando Bloom came into the picture, Katy Perry got real close with Taylor Swift's ex. But her relationship with John was ultra-dramatic. it was constantly on-and-off as they couldn't seem to settle on whether or not they could make things work. Turns out, they couldn't. But for a hot minute, it seemed like John was the one to drive Katy off into the night.

16 Back When Jessica Simpson Was John Mayer's Kryptonite

Daily Mail and Tumblr

When John Mayer was with Jessica Simpson after she split from Nick Lachey, she was one of the hottest commodities in Hollywood. After all, she was a total babe! Mayer himself equated his desire for her to having an obsession. And he's been very candid about his feelings for her post-breakup. However, some bits of information were a tad private. Nonetheless, we can see how addicted he was to her in these photos where they attended a swanky event arm-in-arm.

15 Vanity Fair Snags Those Portraits of John And Katy

Vanity Fair

When John Mayer started dating John Mayer, it made sense that all of their fans wanted them to make some music together... No, not that kind of music, you pervs! Actual music. And they did. Which is why they were intimately photographed together for Vanity Fair. Here we could see that their chemistry was hot as fire.

14 The Secret Poolside Whisperings Of Jennifer Aniston

Daily Mail

Jennifer Aniston was another woman who was just too good for John Mayer. But of course, she dated him. Her track record with men isn't so good. She seems to go for the damaged-goods. And John may be exactly that. But when they were together, their romance was explosive. While they were at the Mandarin Oriental Hotel in Miami for work, they shared sweet-secrets together in the pool while everyone watched... including the paparazzi...

13 The Short Songs Of Colbie Calliat And Vanessa Carlton

Access Online and Tumblr

At two very different times, John Mayer briefly "sung songs" with both Vanessa Carlton and Colbie Caillat. Between 2000 and 2002 he dated the "A Thousand Miles" singer but called it quits to start dating Jennifer Love-Hewitt, another person who seems to have been lost somewhere in that decade. Then in 2009, he spent the summer with Colbie Caillat, a sensitive musician who apparently was devasted when she was dumped. But this is what happens when you date John Mayer.

12 It Was Brief But Demi Lovato Was On The John Wagon Too

Daily Mail

Okay, so John Mayer's fling with Demi Lovato isn't 100% confirmed but they were spotted together in 2016. And they seemed pretty friggin close. in fact, they got very cozy with one another at Catch L.A. in West Hollywood. They seemed pretty familiar with each other in the club but tried to remain cool and collected when they met the paparazzi out front. One thing's for sure, we know Demi could do better.

11 Let's Take A Little Break And Talk About His Randoms... Yep, Those Nobodies

Ig, Just Jared, Pinterest

It's not just famous women who briefly gain access to John's heart... as well as his other things. Over the years, he's been spotted with numerous women. Most of which are pretty spectacularly attractive. But this makes sense since everyone fawns over a handsome musician. We're sure that most of these women knew that things wouldn't last between them. Let's hope this helped build their confidence so they could go off and having relationships with someone deserving of their affection.

10 When Your Woman's As Gorgeous As Jessica Simpson It's Always Photoshoot Time

Tumblr and Pinterest

John Mayer was totally obsessed with Jessica Simpson when he dated her. So it makes sense that he'd use every possible moment for a photo shoot. After all, Jessica is basically photoshoot ready 24/7. The two seemed genuinely close while galavanting by the sea. It's really too bad that he couldn't find it within himself to make it work with this catch.

9 Out For A Stroll With His California Girl

Daily Mail

Here John is going for a stroll with his very own California girl. Both he and Katy dawned their favorite baseball team apparel while on the walk. And it seems to have clashed with one another. After all, he likes the New York Yankees, and she likes the LA Dodgers. Perhaps this was a bit of a sign that things wouldn't end in a home run.

8 How Dare You Hurt Our Mandy Moore!

She Knows and MSN

During the early 2000s, we were very protective of Mandy Moore. She was a Hollywood sweetheart. So, we weren't thrilled with John Mayer after it seemed like he ended things with her. Although, for the record, both of their reps claimed nothing serious went down between them. Then again, the photos speak for themselves.

7 It's All Smiles With John Until Rachel Found Out She Wasn't His Lobster


Yeah, the title is a Friends reference, if you don't get it... shame on you... Anyway, it really did feel like Jennifer Aniston thought John Mayer was his lobster. And to be fair, she did seem to leave her mark on him. Mayer has even claimed that Aniston was "the one who got away". However, he also slammed her publically by saying that she was basically technology-illiterate and a "grandma". Maybe it was comments like this that led to Aniston realizing she could do better.

6 You're Basically A "Supreme" If You Date Minka Kelly

She Knows and Just Jared

No wonder he wore a shirt that said "supreme", you basically are when you land a girl as fantastic as Minka Kelly. And in 2007, when these photos were taken, it seemed like he knew this. However, he clearly didn't dwell on this for long as he was happy to move on. Mind you, Minka seems to be living a better life now that she's no longer with Mr. Supreme.

5 Before John Made it, Jennifer Love Hewitt Was The Star In The Relationship

She Knows

When John Mayer first started to date actor Jennifer Love-Hewitt, she was the star in the relationship. He hadn't begun to make it big. His hit single, "No Such Thing", hadn't yet hit the jackpot. At the time, he seemed devoted to her and supposedly even based his son, "Your Body Is A Wonderland" on her. But this hot and heavy romance swiftly ended. Now that Jennifer Love-Hewitt has more than moved on, she claims she doesn't have any regrets about her past flings.

4 John And Jen Get Real Fancy At The Vanity Fair Party

Vanity Fair and Getty

If you look at these photos from the Vanity Fair party after The Academy Awards, you'd think that Jennifer Aniston was meant to be with John Mayer. After all, he seems to be looking at her with the same amount of lust, love, and appreciation as she does him. At least Jennifer got to experience moments of this with the notorious player.

3 Rumor Has It John Mayer Has A Thing For Blond Bombshells

Just jared, Access Online, And IG

John Mayer has been linked to quite a few blond other than Jennifer Aniston and Taylor Swift. Only, the relationships aren't 100% confirmed. In 2011, Renee Zellweger spent a lot of time with John Mayer. And before that, Cameron Diaz was spotted alone with him after her break-up with Justin Timberlake. Even Halsey was recently rumored to be with him, although both of them have denied it. Still, we wouldn't put it past John to try and get with these talented women.

2 Rumor Has It John Mayer ALSO Has A Thing For Brunette Bombshells

Access Hollywood, IG, and People

But it's not just blonds. Besides Katy Perry, Jennifer Love Hewitt, and Minka Kelly, Mayer has been romantically tied to Kim Kardashian, Shanae Grimes, and British actor Rhona Mitra back in 2005. After Mayer's split with Jennifer Aniston, he apparently got with Rhasida Jones, as well. But she was happy to move on to bigger and better things.

Recently, he's been linked to Cazzie David (Larry's daughter and the ex of Pete Davidson). Although they both claim to be friends, Mayer seems to have a bit of chemistry with the hilarious brunette who's half his age.

1 Swift Fans Are Just Never Gonna Forgive Him


John Mayer's relationship with Taylor Swift was really short-lived. But Taylor's fans act as though he broke her heart. And maybe he did. After all, the dude has a history of getting hot and heavy with women until he feels bored with them. Yeah, it's not a great quality, is it? But it did seem like the two were comfortable with each other while they were dating. Hopefully, they both got something positive out of it and not just MO for a couple of songs.

Sources: Standard.co.uk, The Richest, MSN, Ranker, Too Fab, Page Six, Daily Mail, Vanity Fair

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