For some reason, from the moment John Mayer burst onto the music scene in 2001, he has had a reputation as a ladies’ man, with several very high-profile paramours in his dating history. Many famous women — tall and short, younger and older, blond and brunette — have had the (dis)pleasure of being tied to the singer, and he’s done little himself to stop any rumors. In fact, his reputation as loose-tongued (with the press, thankyouverymuch) has embarrassed many of his previous partners, and eventually himself. From telling Rolling Stone that his perfect partner would need to have a “beautiful” you-know-what that he “could pitch a tent on” (ew) to later excusing himself because “I’m a young guy. I like girls. … I want to make music and be thought of as attractive” (per The New York Times), Mayer is famous for putting his foot in his mouth.

Now that he’s in his early 40s, he’s ready to get serious about his music, and perhaps his relationships too. He hasn’t dated anyone for several years, since his last failed relationship, and the single “Still Feel Like Your Man” from his 2017 album The Search for Everything is about that ex. With Mayer set to perform at the 2021 Grammys, let’s take a look at some of his most famous ex-girlfriends.

What do Katy Perry and Jennifer Aniston have in common? John Mayer

Any retrospective of John Mayer’s dating history has to start with Jennifer Love Hewitt, often thought to be the woman behind Mayer’s biggest hit, “Your Body is a Wonderland.” But the song came out a year before the pair started dating, so anyone paying attention would know that’s not the case. Afterward, Mayer dated songster Vanessa Carlton for about a year, per Wonderwall, and she later called him a “bad breaker-upper.”

Mayer’s big mouth struck again big time while dating Jessica Simpson, who he infamously told Playboy is “like crack cocaine to me,” calling her “sexual napalm.” Whoa dude! At least he regrets saying it.

Brief relationships followed with Cameron Diaz, Minka Kelly, and Jennifer Aniston, but perhaps the most infamous of Mayer’s past girlfriends is Taylor Swift, who may or may not have written her 2010 song “Dear John” about him. Per Rolling Stone, Mayer was “humiliated” by the song, in which Swift sang that she was “too young to be messed with” (she was 19 to his 32), but she has never said officially who the song is about.

Mayer’s longest and most recent relationship was with Katy Perry, who he dated from 2012 to 2014, and again in 2015, before she found love with Orlando Bloom. His 2017 song “Still Feel Like Your Man” is “pretty plainly” about Perry, according to The New York Times. He told the Times, “Who else would I be thinking about?” Hopefully, the Casanova will find love again now that he’s older… and hopefully more discreet.

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