Katy Perry & John Mayer Split: A Look At John Mayer’s Relationship Timeline

Above: The many high-profile women of John 'The Player' Mayer

Reports have just come in that John Mayer and Katy Perry have broken up… again. This is a tough pill to swallow for John Mayer fans that were rooting for Katy Perry to be one to finally reel him in after years of public sex confessions and playboy womanizing in Hollywood. Unfortunately, the trend continues, at least for now. So in the wake up the breakup, we take a look back at the long list of sexy skeletons in Mayer’s closet.

We’ll start with the most recent:

Katy Perry (2012 – 2014)

We all thought this was the end. John Mayer had finally been knocked to his senses by the ‘Roar’ singer and settled down, at last. All signs pointed to this being the case: the public interviews together, the couply photoshoots, the ease and contentment which they spoke about one another, and lets not forget, that song. ‘Love Who You Love’ aired on the big screen in Times Square for the whole world to see. Can you find a greater affirmation of love than that? Now it’s nothing more than a painful reminder of yet another highly publicized relationship that didn’t last. At least the song is a hit.

Last Laugh: Nobody is laughing, it’s actually kind of sad.

Taylor Swift (2009)

They had a brief fling at the end of 2009 when they recorded the song ‘Half of my Heart’ together (Hey look, another hit duet). Their romance ended soon after, which led to another smash hit from Taylor with her song titled, ‘Dear John’. In a feeble retaliation attempt, John pegged the song “cheap songwriting”, which clearly was nothing more than a minor aftershock to the song’s great triumph.

Last Laugh: Taylor and her catchy track.

Jennifer Aniston (2008 – 2009)

Their relationship is probably still firmly etched in most of our minds. How could we forget two of Hollywood’s serial dating powerhouses coming together? The primary cause of friction in the relationship: Age and John’s apparent obsession with Twitter. Are you serious? Twitter? Sounds like these two had a very mature arrangement.

Last Laugh: Twitter.

Minka Kelly (2008) 

John had a very brief fling with the Friday Night Lights bombshell, but it ended quickly because of John’s unwillingness to settle down. Once again, it was yet another misstep for John with a girl worth twice his weight in the looks department.

Last Laugh: The guy who is dating Minka Kelly now.

Jessica Simpson (2006 – 2007)

This is probably John’s most talked about past relationship. Their yearlong affair was blasted all over tabloids. For good reason, there were many highlights. Specifically there was John’s 2010 interview with Playboy magazine where he compared Jessica’s sexual prowess to “sexual napalm” and crack cocaine”. Now Jessica has John to thank for throwing her in the category of “sexual royalty”.

Last Laugh: Definitely Jessica and her highly regarded sexual prowess. 

Jennifer Love-Hewitt (2002)

These two dated briefly after his split with Vanessa Carlton. Jennifer was also the muse for John’s monster hit ‘Your Body is a Wonderland’. Too bad the relationship didn’t last long enough to see the song’s massive success. The couple broke up soon thereafter.

Last Laugh: Anybody who has ever dedicated this song to a loved one and received massive amounts of brownie points in doing so.

Vanessa Carlton (2002) 

These two dated in early 2002 when both of their careers were on the rise. Years later, Vanessa came out as being bisexual.

Last Laugh: Hard to say.

Poor John Mayer. But we can’t really feel too sorry for him, can we? He did get to enjoy the company of all these beautiful women. But the fact that he let all these women fall by the wayside is up to him and his conscious to wrestle with now.

Tags: Jennifer Aniston, John Mayer

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