John Mayer's Love Life in 6 Photos

The ladies' man has dated his fair share of Hollywood's finest stars -- but could he have finally found the one?

John Mayer has never sustained a relationship for more than a year, and he's been known to give really embarrassing interviews about his exes. Nevertheless, women can't help falling in love with the temperamental singer-songwriter.

It's not hard to figure out why: in spite of everything else, he's cute, he's smart, and he writes a killer love song. Katy Perry certainly seems hooked.

As the singer celebrates his 36th birthday, let's take a look at a few of the other women who have given Mayer a shot.

 

Vanessa Carlton (Dated 2002-2003)

Vanessa Carlton

L. Cohen/WireImage

Relationship Highlight: Back when they were both new to the Hot 100, Mayer dated the singer-songwriter behind "A Thousand Miles." They went public via an announcement on Carlton's official message board.

How it Ended:
After about a year, John broke things off. Carlton has since described him as a "bad breaker-upper." More details, please, Vanessa!

 

 
 

Jessica Simpson (Dated 2006-2007)

Jessica Simpson

Brian Ach/WireImage

Relationship Highlight: Mayer's relationship with Simpson began around the time her divorce from Nick Lachey was finalized. In 2007, she joined him on his Continuum tour in Australia, where they were photographed taking a barefoot walk on the beach.

How it Ended: Following several weeks of break-ups and make-ups, John and Jessica ended things for good in 2007. Simpson was diplomatic about the break-up, telling Elle in 2008 that "John is going to be an amazing man for someone, but I know that I was supposed to be with someone else." Two years later, Mayer crassly compared Simpson to "sexual napalm" and "crack cocaine" in his infamous Rolling Stone interview.

 


 

Minka Kelly (Dated 2007)

Minka Kelly

James Devaney/WireImage

Relationship Highlight: After dating for around a month, John and the Friday Night Lights actress gave fans a front row seat to their romance: they were photographed making googly eyes in the courtside seats at a Knicks game.

How it Ended: The relationship ended without fanfare after two or three months. After John moved on with Jennifer Aniston, Minka politely told People that she was "really happy" for him. (Ironically, John reportedly once told Minka, "I don't really get this Jennifer Aniston thing.")

 


 

Jennifer Aniston (Dated April 2008-August 2008, October 2008-March 2009)

Jennifer Aniston

Kevin Mazur/VF/WireImage for Vanity Fair

Relationship Highlight: Mayer and Aniston made their public debut as a couple at the 2009 Oscars -- which was appropriate, since they'd first met at an Oscar party the year before. "I deeply, deeply care about him ... we adore one another. And that's where it is," Aniston told Vogue.

How it Ended: The couple split briefly in 2008 , then made a permanent break just weeks after their 2009 Valentine's Day getaway to the Bahamas. "I've never really gotten over it," Mayer confessed to Rolling Stone in 2010. "That woman was the most communicative, sweetest, kindest person . . . It’s been a deep relationship, and it’s no longer taking place at all. Have you ever loved somebody, loved her completely, but had to end the relationship for life reasons?"


 

Taylor Swift (Dated 2009-2010)

Taylor Swift

Dimitrios Kambouris/Getty Images for VEVO

Relationship Highlight: John and Taylor have never officially confirmed their fling, but it seems to have begun around the time they recorded the duet "Half of My Heart." She was 19; he was 31.

How it Ended: Judging from all the bitter song lyrics and cagey interviews that followed, we're going to say "badly." Mayer told Rolling Stone he was "humiliated" when Swift released her 2010 song "Dear John" (which contains the line "don't you think I was too young to be messed with?"). In 2013, Mayer released the single "Paper Doll," which appears to tell his side of the break-up.


 

Katy Perry (Dated June 2012-August 2012, September 2012-March 2013, July 2013-Present)

Katy Perry

Larry Busacca/Getty Images for NARAS

Relationship Highlight: They've broken up twice, but somehow, Katy and John keep coming back to each other. Our first hint that things were getting serious came this summer, when John opened his Born and Raised tour with a heartfelt song dedication."This is a long time coming for the both of us," said Mayer, after describing how Katy got him through the toughest months of his life. "I wanna dedicate this next song to my Katy, who is my face to call home." Engagement rumors come and go, but the couple is still going strong: Perry recently gushed to Billboard about "my boyfriend," calling him "literally a genius."

 

WATCH: Katy Perry and John Mayer to Get Engaged 

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