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Jennifer Love Hewitt
Jennifer Love Hewitt

Jennifer Love Hewitt was Mayer's first celebrity love. The two dated in 2002, right at the beginning of his success. They were not very public about their relationship, but they dated for over a year. Luckily for us, one of his BEST songs reportedly resulted from this relationship...

Jennifer Love Hewitt
Jennifer Love Hewitt

Yep, that's right! Rumor has it that John Mayer wrote the song "Your Body is a Wonderland" about Love Hewitt. According to the song, the two had steamy bedroom chemistry and Mayer enjoyed using his hands for more than just playing his guitar. This wouldn't be the first time details about Mayer's bedroom habits would surface, either. 

Rhona Mitra
Rhona Mitra

After breaking up with Hewitt, Mayer started dating Mitra, the fierce British bombshell. Her piercing eyes and stolid smile must have pushed Mayer over the "Edge of Desire".

Jessica Simpson
Jessica Simpson

Mayer's relationship with Jessica Simpson marked the beginning of his public image as a serial dater. Before that, he chose to shy away from the press and keep his personal life private. However, after he began seeing Jessica, his name started appearing in the tabloids, as the two attended clubs and events together.

Jessica Simpson
Jessica Simpson

What surprised many about the Jessica-John saga was John's explicit comments about her post-breakup. In a March 2010 interview with "Playboy," Mayer (then 32 years old) didn't shy away from revealing what kept him in that relationship: "That girl is like crack cocaine to me. Sexually it was crazy...Did you ever say, 'I want to quit my life and just f*****' snort you? If you charged me $10,000 to f*** you, I would start selling all my s*** just to keep f****** you.'" Well okay, then. 

Katy Perry
Katy Perry

It's hard to deny out great looking Mayer and pop star Katy Perry were as a couple. So where did it all go wrong? 

Katy Perry

Wikimedia Commons

Katy Perry

After Katy Perry broke up with comedian Russell Brand, she took up with Mayer. The two developed a personal and professional relationship and even recorded a song together for Mayer's "Paradise Valley" album. They even shared a stage together at one point. However, it proved to be an on and off relationship for a while and the two just weren't compatible in the end. (Perry is reportedly now dating Orlando Bloom). 

Minka Kelly
Minka Kelly

Minka and Mayer went out for a few months in 2007. The relationship was short-lived and reportedly, Mayer ended it. It is hard to say if the breakup left Minka brokenhearted, but she went on to date Derek Jeter, whom she dated for three years. And we all know who Mayer took up with afterwards....

Jennifer Aniston
Jennifer Aniston

Mayer was one of Jennifer Aniston's most famous "post Brad" relationships. They started dating in 2008 and had an on-and-off relationship for over a year. 

Jennifer Aniston
Jennifer Aniston

While they had their fair share of romantic getaways, Jen reportedly ended the relationship because John spent more time on Twitter than with her and she felt he was avoiding her. It all turned out okay, though, as Aniston is now head over heels with her new hubby Justin Theroux. 

Taylor Swift
Taylor Swift

Taylor Swift has notoriously bad luck with relationships and seems drawn to players, so it's no surprise that she went out with Mayer. The two briefly dated after they recorded a song together. It didn't last, and brokenhearted Taylor wrote a song called "Dear John" about the experience.

Cameron Diaz
Cameron Diaz

Rumor has it that Mayer and Cameron briefly dated at the end of 2007. Although neither has confirmed or denied it, the two were seen cuddling by the fireplace in a New York City hotel. As Cameron is fairly open to having casual relationships, this one isn't much of a surprise.

Kim Kardashian
Kim Kardashian

This relationship is another rumor, but it is fairly plausible. Like Mayer, Kim was a serial dater who was linked to many big names in entertainment before she married Kanye West. If this rumor is true, Kim and Mayer went out sometime in October, 2010. Unsurprisingly, the relationship didn't last very long.

Miley Cyrus
Miley Cyrus

At the 2011 Grammys, Mayer and Miley were reportedly seen kissing backstage. Miley apparently has a thing for older guys because she is 15 years younger than Mayer. Maybe Mayer should consider changing his hit "Half of My Heart" to "Half of My Age".

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