John Mayer is known for the song "Your Body is a Wonderland," which earned him the Grammy Award for Best Male Pop Vocal Performance. While the single was a commercial success, the lyrics are not as innocent as it sounds. On top of that, the pop guitarist is entirely known as a kiss-and-tell playboy due to his interviews and the tabloid coverage of him. Nevertheless, he is one of the many musicians who were able to date Hollywood's elite.

Jennifer Love Hewitt

The "I Know What You Did Last Summer" star, and the guitarist were said to be dating back in 2002. The relationship was brief, but it was also the time when "Your Body is a Wonderland" was released. This led to the speculation that the song was about Hewitt.

Mayer denied that the song was dedicated to her and, instead, confirmed that it was for his first girlfriend he dated when he was 14.

In a 2018 interview, the "Can't Hardly Wait" actress shared that she believed the song was not written for her specifically. However, she accepts the compliment that fans thought it was about her or her body.

Kiss-And-Tell Hollywood Playboy? John Mayer's Celebrity Ex-Girlfriends
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Katy Perry

The two pop musicians were "on and off" for two years before Perry finally moved on with "The Lord of the Rings" actor and current partner Orlando Bloom. Friends close to both Perry and Mayer said that the couple wanted to make it work but are too different to get along.

In 2017, Katy Perry was challenged by late show host James Corden to a game where they are given the option to either tell a personal detail about themselves or choose to eat disgusting food.

When asked who the better lover is, the "I Kissed a Girl" singer revealed Mayer to be the top one while Bloom was second and Diplo was third. During this time, Perry and Bloom broke up, but they eventually got back together.

Jennifer Aniston

The "F.R.I.E.N.D.S." star and the pop guitarist started dating in 2008 after the two got close at the Oscar party. The two broke up due to the vast eight-year gap between them. Though he shared his thoughts about the break up in a Playboy interview, the two remained friends.

Jessica Simpson

Perhaps the most controversial relationship Mayer had was with pop singer-actress Jessica Simpson. They began dating in 2005, but Simpson ended the relationship two years. In a Playboy interview, Mayer shared that Simpson was "sexual napalm."

The comments caught the "I Wanna Love You Forever" singer off guard, and she shared her thoughts about it on her memoir "Open Book."

"I was floored and embarrassed that my grandmother was gonna read that."

Mayer apologized for the remarks and decided to stay out of the spotlight.

Taylor Swift

There were rumors that the two talented guitarists were dating until Taylor Swift broke the silence with her song "Dear John." The song is about how the country-pop princess was mistreated and how she did not listen from the warnings.

Mayer felt terrible and believes it was "lousy" for Swift to do. In response, he wrote "Paper Doll," and many thought it was dedicated to the said country-pop star.