Jennifer Aniston and John Mayer

She’s a respected (kind of) actress. He’s a respected (kind of) musician. But when they hooked up, the match was bizarre enough to have everyone asking, “Really?” In April 2008, when whispers that Jennifer Aniston and John Mayer were hooking up started, it seemed the budding romance between the queen of the small screen, who was taking the cutthroat world of bad romantic comedies by storm, and the rock guitarist, who couldn’t stop talking or tweeting, was doomed from the start. She was a megastar who couldn’t get a haircut without it being front page news. He was a talented guitarist who constantly dangled his personal life in front of the media in an effort to get attention. They were both serial daters with horrible track records for maintaining lasting relationships. There was also the small matter of the age differences—she is eight years older than Mayer.
But none of that seemed to matter when, a month later, they were a bona fide couple. At first, there was speculation that they met through mutual friend Sheryl Crow. Then People reported that they had met even earlier, at a pre-Oscar party thrown by talent agency CAA. Sources said that Aniston was the aggressor, initiating contact via flirtatious emails with Mayer before inviting him out for some sun and fun at the Mandarin Oriental in Miami where she was shooting Marley & Me. Unlike mere mortals, celebrity dates usually entail planes, four-star hotels and butler service.
They quickly became Hollywood’s “it” couple, more for the sheer novelty of their union than anything. It also helped that Mayer, an internet social networking addict, liked to post personal information on his Twitter on an hourly basis. They were photographed at every step—her backstage at his shows, sharing a kiss at her Marley & Me wrap party, vacationing, out on the town.
Then their romance came to an abrupt end in August 2008. There were reports that Jen ended the relationship when she got fed up with John’s constant tweeting. Others said Mayer ended it because he couldn’t handle the pressure of dating such a huge star. Taking a cue from the Douchebag’s Guide to Life, Mayer held an impromptu press conference outside of his gym in New York to explain the split saying, “I ended a relationship to be alone because I don't want to waste somebody’s time if something’s not right.”
Clearly Jen is the forgiving type because she was back in his arms two months later. Aniston confirmed that they were back together in November when she appeared on The Oprah Winfrey Show.
Their relationship only heated up from there. In February 2009, Mayer and Aniston did the Hollywood equivalent of exchanging vows on live national television when he escorted her to the Oscars. They skipped the red carpet (and a potential run-in with her ex-husband, Brad Pitt, and his new beau, Angelina Jolie), but Gayle King caught up with them backstage where they said they are “very happy.” Rumors immediately started to swirl that they were on the brink of getting engaged. Mayer’s joke tweets about shopping for a ring did not help.
But they were clearly not happy enough. Weeks later, they were kaput again. According to sources, it was the last straw when John’s tweeting started to take precedence over their relationship (maybe that ring joke wasn’t the best idea). Reports suggested that he stopped returning emails and phone calls claiming he was too busy working, but, to Jen’s displeasure, his Twitter account continued to be inundated with updates. Shortly after she called it off, he tweeted, “This heart didn’t come with instructions.” That probably destroyed any lingering hopes of a reconciliation.
Despite the public waiting patiently for another reunion, this time, the split was for good. There were rumors that Aniston dated Bradley Cooper and Gerard Butler, but nothing was confirmed. Mayer, meanwhile, claimed he never got over the Friends star. In a candid interview with Rolling Stone for their January 2010 issue, he admitted, “I’ve never really gotten over it. It was one of the worst times of my life.” He also talked about masturbating his way out of difficult times and finding the Joshua Tree of vaginas.
But in case that didn’t make the public cringe enough, he followed it up with another controversial interview with Playboy the following month in which he called his ex Jessica Simpson “sexual napalm,” tossed out the N-word and said that he was the one who ended his relationship with Jen. “I’ll always be sorry that it didn’t last. In some ways I wish I could be with her. But I can’t change the fact that I need to be 32,” he explained. Apparently, 32 is the new 12 and clueless.

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