For years, John Mayer was known for not only being an incredible songwriter and singer, but as Hollywood’s most famous playboy. Mayer has been linked romantically with quite a number of A-list women, including Jennifer Aniston, Jessica Simpson, and more. It’s almost too hard to keep track of all the women Mayer has dated, but we’ll do our best to list the biggest names.
Simpson and Mayer began dating in the summer of 2006. The two’s relationship was fodder for tabloids, even before Mayer’s controversial 2010 Playboy interview in which he described the pop star as “sexual napalm.” Simpson later described her reaction to the interview in her memoir, Open Book, as transcribed by Entertainment Tonight. “He thought that was what I wanted to be called. I was floored and embarrassed that my grandmother was actually gonna read that,” Simpson wrote. “A woman and how they are in bed is not something that is ever talked about. It was shocking.” By the end of 2006, the couple had broken up for good.
Aniston is probably the strangest name on this list, but it’s a matter of fact that the Friends actress dated John Mayer. They met in February 2008 at an Oscars party and hit it off. The good times didn’t last, though, and Mayer hosted a bizarre press conference outside his gym in August of that same year, declaring “I’m the a—hole. I burned the American flag. I basically murdered an ideal.” Like many of Mayer’s breakups, though, this one didn’t last too long. He was Aniston’s Oscars date in 2009, but just one month later, they broke up again.
Taylor Swift and John Mayer are both famous for their extensive dating history, so it seemed a little inevitable that they’d eventually get together. Their time finally came in 2010, but it wasn’t meant to last. After their breakup that same year, Swift wrote her song, “Dear John” about their relationship. Mayer didn’t care for that too much, and spoke to Rolling Stone about the betrayal he felt about the song. “I never got an e-mail. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?” He told the outlet. Safe to say that this couple is never, ever, ever getting back together.
Katy Perry and John Mayer enjoyed an on-again-off-again for about a year and a half between 2012 and 2014. The pair first sparked rumors of a romance when they were seen dining out together then heading to the Chateau Marmont. The relationship may have started out casually, but by March 2013, they called it quits. An anonymous source spoke with E! News, telling them, “John still very much loves [Perry] and has feelings for her. It was just going to be too much with what was on his plate.” The break didn’t last long, with Perry and Mayer getting back together just a few short months later. Alas, like their short breakup in 2013, the romance didn’t stick. The two announced their final breakup in February 2014.
This is only a partial list of all of Mayer’s romantic conquests. He was also linked with Minka Kelly, Cameron Diaz, Vanessa Carlton, and even Jennifer Love-Hewitt. At the moment, Mayer is presumably single, or if he is seeing a special lady, he’s keeping it quiet. That would probably be for the best, considering his past.