John Mayer Dating History

John Mayer dating history reads like a who’s who of Hollywood. No matter how much you love or hate the guy, looking through the list below, you have to admit this singer’s got game. 

  1. Jennifer Love Hewitt. 2002. Having dated America’s sweetheart for a few months, John Mayer crashed and burned when he made raunchy comments about their relationship during a stand-up routine. The butt of his joke? John claimed their relationship was never consummated. In true John fashion, he later apologized. 
  2. Jessica Simpson. 2006. Jessica was a self-proclaimed virgin prior to her much-publicized marriage to singer Nick Lachey. She added to John Mayer’s dating history shortly after her divorce, and Mayer described her as “sexual napalm.” Three words: virgin no more.
  3. Minka Kelly. 2007. She exited John’s life as quickly as she entered it; nothing came of this short relationship in 2007. Minka had nothing on the buxom Jessica Simpson, apparently. “Sexual napalm” is apparently difficult to compete with.
  4. Cameron Diaz. 2007. After splitting from Criss Angel, this funny girl kanoodled with John briefly. Sources spotted them hanging out in NYC on several occasions. The duo never made an official public appearance.
  5. Ricki Lake. 2007. Let’s admit it. After Ricki lost a ton of weight she got pretty hot. But, Ricki Lake as part of John Mayer’s dating history? Apparently, John Mayer agrees about her newfound hotness as he has admitted to having a crush on her. Ricki insists nothing between them happened aside from a brief conversation at a party.
  6. Jennifer Aniston. 2008. When most people think of John Mayer’s dating history, this “friend” comes to mind. They’ve broken up and gotten back together more times than Rachel and Ross. John seems to be perpetually attracted to this cougar and keeps going back for more.
  7. Giada De Laurentiis. 2010. What’s the fastest way to a man’s heart? Through his stomach, of course, and no one knows this better than chef Giada. John’s reportedly hooked up with this MILF, but the rumors have never been confirmed.
  8. Taylor Swift. 2010. Perhaps the oddest chick in John Mayer’s little black book is good-girl, country cutie Taylor Swift. She’s denied the rumors that she’s the latest notch on Mayer’s bedpost and states they just share musical interests. Since she’s notorious for writing songs about past relationships, we’ll be the judge when her next album comes out.
  9. Kim Kardashian. 2010. John can appreciate a nice piece of A…rmenian hotness. And who wouldn’t? These two reportedly got cozy after Kim’s split with NFL player Reggie Bush.
  10. Scheana Marie Jancan. 2010. This aspiring actress and model met John as she served him drinks in a flashy Beverly Hills club. John seemingly prefers fame to obscurity, as this rumored relationship didn’t last long.
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