John Mayer’s Dating History Has People Calling Him The Original Pete Davidson

Pete Davidson is a man who gets around Hollywood women like there’s no tomorrow. From Ariana Grande to Kim Kardashian, he’s got a long list of famous ex-girlfriends to his name, and no doubt he’ll add more in the future. However, many fans are starting to realize that one person did it all before the “SNL” alum. In fact, John Mayer’s dating history would give Davidson a run for his money — you could say he was the original.

  1. Lest we forget, Mayer was a big deal in the early 2000s. He went from playing small-town open mics to major stardom pretty quickly. That meant the dating world suddenly opened up for John Mayer. Lots of women who never would have given him the time of day before started to think twice. He took advantage of that for sure.
  2. He was linked to some very famous faces. In the very early 2000s, John Mayer was first said to be dating Vanessa Carlton. However, that was never actually proven and they never went public. By 2002, however, Mayer got with (and broke up with) “Party of Five” actress Jennifer Love Hewitt. The journey had begun.
  3. A big chunk of John Mayer’s dating history was taken up by Jessica Simpson. They apparently broke up and got back together again nine times between 2006 and 2010, according to Mayer. Apparently, he ended it every time by email, which is a bit crappy. One time, he even sent her the song “Angel” by Aerosmith to break things off. What a guy!
  4. His biggest relationships were yet to come. In 2007, during one of his breaks from his relationship with Simpson, John Mayer was said to be dating (or at least having a fling with) Cameron Diaz. This was shortly after she broke up with Justin Timberlake. She and Mayer were said to be “super flirty” at the time, so take that as you will. He also dated Minka Kelly for a few months that year.
  5. In 2008, John Mayer started dating Jennifer Aniston. It was certainly one of his most high-profile relationships and one of his most public. They only lasted about a year or so before he moved on to Taylor Swift. The pair dated for roughly two years, though she was only 19 at the time and he was 32. He was later honored (?) in her track “Dear John.”
  6. Things didn’t slow down for Mayer from there. In 2010, he was said to be involved with Kim Kardashian, and people claimed he was making out with Miley Cyrus at the Grammys the following year. However, nothing seems to have come of that.
  7. He stayed with Katy Perry for a while. John Mayer and Katy Perry started dating in 2012 and managed to make it work for three years before breaking up. It was the first relationship he felt was really stable and potentially going to last, but obviously, that wasn’t the case.
  8. John Mayer is happily single at the moment. In fact, he’s not looking for love. Appearing on the Call Her Daddy podcast, he admitted he’s sort of over all that. “I don’t really date. And I don’t think that I have to, to be quite honest,” he claimed. “I quit drinking like six years ago, so I don’t have the liquid courage. I just have dry courage.”
Jennifer Still is a writer and editor with more than 10 years of experience. The managing editor of Bolde, she has bylines in Vanity Fair, Business Insider, The New York Times, Glamour, Bon Appetit, and many more. You can follow her on Twitter @jenniferlstill