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John Mayer Turns 36: His Relationship Timeline

Katy Perry & John Mayer

Credit: Photo by Christopher Polk/Getty Images for NARAS

Since stepping into the Hollywood scene with his debut album Room For Squares in 2001, John Mayer has continuously been dubbed a womanizing, bad boy. Today, the singer celebrates his 36th birthday, and if his current relationship status is any indication, he’s finally matured.

“happy birthday cutie!!!” John’s serious girlfriend, Katy Perry, tweeted at him. The couple has been dating on and off since 2012, and while it looks like the “Paper Doll” singer is finally settling down, let’s not forget about the several famous faces he’s dated in the past.

Vanessa Carlton

Vanessa Carlton

2002 was a big year for both of these singers, who were enjoying their initial success in Hollywood. They dated on and off for a year before eventually deciding to call it quits, and years later, Vanessa came out as bisexual.

Jennifer Love-Hewitt

Jennifer Love Hewitt

John and Jennifer dated only briefly after his breakup with Vanessa, but their romance became highly publicized — especially later on, when he used it as a subject for a comedy routine! The singer joked about how he never got to have sex with his ex during their short relationship, and he says he eventually apologized to her for the jokes.

Jessica Simpson

Jessica Simpson & John Mayer

These two were all over magazines during their year-long relationship from 2006-2007, and for years after, people still talked about it. That mostly has to do with John’s 2010 Playboy interview, though. “Sexually, it was crazy,” he said of their romance. “That’s all I’ll say. It was like napalm, sexual napalm.” He also compared Jess to “crack cocaine” while explicitly discussing their previous sexual relationship.

Minka Kelly

Minka Kelly

After his split with the now-mom of two, the singer dabbled in some fun with Minka. Although their relationship did last a few months, and they were spotted out at Hollywood hotspots on several occasions, John was once again not ready to settle down. They called things off in early 2008.

Jennifer Aniston

Jennifer Aniston & John Mayer

Like John, Jennifer was no stranger to dating in Hollywood. Tabloids exploded once again when these two hooked up in 2008, and their relationship was quite the subject of media frenzy for it’s year long duration. Alas, Jennifer met the same fate as Jessica, when John dished about her in his Playboy interview, admitting that age was the factor in their split.

“One of the most significant differences between us is that I was tweeting,” he said, adding, “The brunt of her success came before TMZ and Twitter. I think that she’s still hoping it goes back to 1998.” Still, John revealed that he wanted things to work out with the We’re the Millers star. “In some ways, I wish I could be with her, but I can’t change the fact that I need to be 32,” he admitted at the time.

Taylor Swift

John Mayer & Taylor Swift

Moving on from one serial dater to the next, John courted the much younger Taylor toward the end of 2009. They recorded the duet “Half of my Heart” together, but called things off early the next year. Later, Taylor penned the song “Dear John” about her ex, and it appeared on her 2010 album Speak Now. Years later, John criticized the tune and dubbed it as “cheap songwriting.” Ouch.

Katy Perry

Katy Perry & John Mayer

After his breakup, John stayed single for awhile, embarking on a few flings before making it official with Katy. They’ve broken up twice, which many have attributed to the singer returning to his womanizing ways, but since their reconciliation over the summer, things seem to be going well for the couple.


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