John Mayer Girlfriends- Who Has John Mayer Dated Until Now

Who were John Mayer girlfriends to date?

John Mayer, one of the most talented musicians in the industry, is perhaps known for his playboy reputation equally. His reputation can be credited to his numerous affairs and his short-lived relationship with some of the prominent female celebrities of Hollywood.

His good looks and ear-melting voice make the opposite sex go crazy over him.

We include a list of John Mayer’s girlfriends who are publicly known or rumored to have been dating the singer of Your Body is Wonderland.

John Mayer’s Girlfriends list-

Vanessa Carlton (2002)

Vanessa is the first one publicly known in the John Mayer Girlfriends list.

In 2002, John Mayer was rumored to have two relationships simultaneously, we assume. The first romantic relationship was with Vanessa Carlton. 

Vanessa, just like John, was busy with their career. Their relationship was short-lived as John started focusing on wooing another woman in 2002- Jennifer Love Hewitt. 

Jennifer Love Hewitt (2002 – 2003)

John Mayer started dating Jennifer Love Hewitt in 2002 after breaking up with Vanessa Carlton. He wasn’t famous, or at least as prominent as Jennifer was. You can say that John was head over heels for her.

Additionally, his hit song Your Body is Wonderland was rumored to have been written for her. In December 2022, in a podcast, John Mayer cleared the air around it and said the song was about his first high school girlfriend.  

Rhona Mitra (2005)

John Mayer’s name was linked with many women, which were rumors or true no one has the answer. One of the female celebrities was the British actress Rhona Mitra. It is believed that they hooked for a few months. However, they both have tried to keep the matter hush-hush.

Milana Vayntrub (2006)

Milana is another woman who has never confirmed the rumors. Milana Vayntrub is another unofficial John Mayer girlfriend. However, she was only 19, and John was 28.

Jessica Simpson (2006-2007)

After breaking up with Nick Lachey, Jessica Simpson started dating John Mayer. They dated for a year. In an interview with Playboy, Mayer said Jessica is her sexual napalm. He even went on to say that “sexually it was crazy” and that “it was like napalm, sexual napalm.” Jessica deleted his phone number after she saw the interview. 

Cameron Diaz (2007)

The relationship between Cameron and John Mayer can be said to be a rebound. Cameron Diaz had just broken up with Justin Timberlake. Soon Mayer was seen flirting with Cameron. They were dating in New York City; however, their relationship fizzled within a few months. As a result, it was perhaps a rebound.

Minka Kelly (2007)

John then started dating Minka Kelly in 2007. But it was short-lived, too. Again it could be because he was attracted to Jennifer Anniston and wanted to be with her.

Jennifer Aniston (2008)

 In 2008 he started seeing Jennifer Aniston. However, it was an on-off relationship. John even admitted sleeping with other women during their off period. They ended their relationship in 2009 but are still friends.

Additionally, he wrote a song, Shadow Days which was about Jennifer Aniston. In an interview, he told Playboy, “That woman was the most communicative, sweetest, kindest person.” 

Taylor Swift (2009)

Another high-profile female celebrity he dated was Taylor Swift. The duo dated from 2009-2010. Their breakup was probably tough for Taylor as she wrote a son Dear John about him. However, Taylor never admitted that the song was about him.

Kate Perry (2012-2015)

 After breaking up with Taylor, he dated Kate Perry. It was one of the longest relationships. Kate and John dated from 2012 to 2015. However, three years after their relationship was over, he wrote a song, Still Feel Like Your Man, which was about his relationship with Kate Perry. 

Related: Katy Perry John Mayer Relationship- Everything You Didn’t Know

Kiernan Shipka (2020)

 In 2020, there were rumors again that he was dating the actress Kiernan Shipka who is 22 years younger than him. They were seen drinking and hugging in Hollywood in February 2022. None have confirmed the rumors.