The many train-wreck romances of John Mayer

Love him or hate him, John Mayer has made some serious headway in the world of Hollywood dating. From a fling with Jennifer Love Hewitt to his current relationship with Katy Perry, it’s clear that the 35-year-old musician has a thing for A-list women…and lots of them.

With Perry as his newest target/love interest, it seems as if Mayer is off the market yet again. But as his previous relationships have proved, this love probably won’t be his last. Here, I’ve rounded up my favorite former flames of the infamous serial dater. (Hey, he’s got to get his love-song inspiration from somewhere.)

Katy Perry
The former Mrs. Russell Brand is now John's new arm candy (or is it the other way around?). Either way, it's clear that the pop star prefers her men tall, dark and goofy.Jennifer Love Hewitt
As adorable as John sounds while crooning "Your Body is a Wonderland", keep in mind that he's referring to Jennifer Love Hewitt and not,well...you. These two split over 10 years ago, but that doesn't mean they shouldn’t reunite.

Jennifer Aniston
Despite nearly a 10-year age difference, the singer dated Aniston for a year before calling it quits in March 2009. Since their breakup, Mayer has been quoted saying, "I'll always be sorry that it didn't last." But that alone didn't stop him from moving forward with yet another Hollywood star...

Taylor Swift
Ah, the one who got away (and later wrote a song about it). The country star and fellow serial dater was linked to Mayer for two months before things supposedly went sour. In true Swift fashion, the songstress titled her next tune "Dear John." Gosh, Taylor -- who could that one be about?

Cameron Diaz
These two A-listers dated, albeit briefly, in 2007 and cooled off after just one month. But let's be honest -- who hasn't Diaz dated? From Justin Timberlake to Tyrese Gibson, she's got most of Hollywood covered. (I’m jealous, not judgmental.)

Jessica Simpson
Mayer dated good-girl Simpson soon after her split from husband Nick Lachey in 2006. (If that doesn't scream rebound, I don't know what does.) After a year together, the two went their separate ways -- but not before Mayer compared Simpson to "sexual napalm." Keepin' it classy, I see.

Minka Kelly
Believe it or not, there was life before (and after) Derek Jeter. The actress was briefly linked to Mayer in 2007, but he allegedly ended things after only a few months. Apparently the words "Minka Kelly" and "dumped" can exist in the same sentence. Who knew?


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