He dated Minka Kelly (of Friday Night Lights) for a minute but his superstar (or Notting Hill, depending on your POV) moment came when he hooked up with Jennifer Aniston. The rumors swelled to scandal proportions and Mayer bravely faced the paparazzi firing squad. Sure privacy is great, but what guy wouldn't want everyone to know he's dating an A-Lister? Shout it from the rooftops, brah.
But, because Mayer is a regular dude, the media scrutiny got to be too much and the relationship moved too fast for him. The photog's flashbulbs must have some time-warping property. He didn't realize that Hollyweird romances move faster the farther up the food chain you go. And, like high school, sometimes things get a little weird and other people’s perceptions make mole hills mountains. And as quickly as things came together, they come apart (that's what she said?).
Like any guy, he'd prefer to think that the breakup was initiated by him or at least mutual (and who's to say he's wrong?). But the paps were still all up in his junk (has anyone ever called this a pap smear? If not… FIRST!), so he felt like he had to say something because regular guys have a really hard time saying nothing. And then because WE (both the media and the celeb-crazy populace) got what we wanted from him, some inside dirt, we could cast him to the side… fait accompli. So he caught the villain rep for talking out-of-school about private things, even though we begged him for it. The Aniston side more cleverly used proxies to get their of the story side out. John Mayer just could not win. Men, especially regular dudes, really struggle with the concept of the dis by proxy thought we are willing to talk trash about our sports teams' successes.
And then he had regrets. Pretty standard. Normal guys don't like being alone. And he'd already stepped in the wolf trap of negative public sentiment. What starlet was going to immediately give him a chance with the Aniston evil eye roving the country side like a lighthouse? And he couldn't go back to non-famous girls (sure, as a goof but not as a girlf). So, he started with the texts and admitted his mistakes, as all of us regular guys do. And, inexplicably, it must have worked at some level as the 2 have been seen out again.