Unveiling John Mayer's Secret Love Affairs: From Jessica Simpson and Jennifer Aniston to Katy Perry and Beyond

John Mayer, acknowledging his own role in his romantic misfortunes, has experienced a streak of bad luck in love.

During the beginning stages of his career, the renowned singer of "Gravity" enjoyed a high-profile dating life, involving notable individuals such as Jennifer Love Hewitt and Jessica Simpson. Unfortunately, his rockstar mentality eventually backfired when he faced backlash for his controversial and highly publicized interviews, particularly the Playboy incident where he referred to his relationship with Simpson as "sexual napalm."

Initially, the Grammy winner expressed no remorse - he stated in a March 2017 profile with The New York Times, "I want girls to like me. I want to make music and be seen as attractive." However, as time went on, he came to realize that he had created his own source of controversy, comparing it to a grenade he had invented, as he later told the Times.

Following the end of his relationship with Simpson, Mayer went on to date Jennifer Aniston, Taylor Swift, and Katy Perry, causing their romances to capture both headlines and inspire songs. For quite some time, fans have speculated that Swift wrote several tracks about Mayer, such as "Dear John" from Speak Now and "Would've, Could've, Should've" from Midnights. Similarly, Mayer's song "Paper Doll" is rumored to be about the "Anti-Hero" artist. Additionally, Mayer openly admitted to writing music inspired by Perry.

Mayer hasn't been in a committed relationship since his breakup with Perry in 2014, but he does have a desire to get married. In a late 2022 episode of the "Call Her Daddy" podcast, he expressed his intention to tie the knot. Take a look below for a list of Mayer's high-profile relationships over the years.

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John Mayer’s Dating History: Jessica Simpson, Jennifer Aniston, Katy Perry and More

John Mayer has been unlucky in love — and he’ll be the first to admit that he’s partially to blame.

During the early days of his career, the singer of "Gravity" experienced a surge of success as he went on dates with notable figures such as Jennifer Love Hewitt and Jessica Simpson. However, his rockstar mentality led to criticism when he participated in a series of notorious interviews where he openly discussed his high-profile relationships — including the well-known incident involving Playboy, where he used the phrase "sexual napalm" to describe his love affair with Simpson.

Initially, the Grammy winner showed no remorse, stating in a March 2017 profile for The New York Times, "I desire female admiration. I aspire to create music and be seen as attractive." Nevertheless, with the passage of time, he began to realize the negative impact he had created for himself. He confessed to The Times, "I had inadvertently created a destructive force."

Following his failed romance with Simpson, Mayer went on to date Jennifer Aniston, Taylor Swift, and Katy Perry, attracting attention and inspiring songs in the process. Fans have speculated that several of Swift's tracks, such as "Dear John" from Speak Now and "Would've, Could've, Should've" from Midnights, were written about Mayer, while his song "Paper Doll" is rumored to be about the "Anti-Hero" artist. Mayer has also openly admitted to crafting music inspired by Perry.

Although the Room for Squares singer has not been involved in a serious relationship since splitting from Perry in 2014, he still desires marriage. Speaking on the "Call Her Daddy" podcast in late 2022, he expressed, "Of course I want to get married."

Keep scrolling to see Mayer's A-list romances throughout the years:

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Jennifer Love Hewitt

The musician and the actress from I Know What You Did Last Summer were in a relationship in 2002. There were widespread rumors that he wrote the song "Your Body Is a Wonderland" about her. However, in a 2022 interview on the "Call Her Daddy" podcast, Mayer disclosed that the song was actually about his "first girlfriend" and not someone famous.

In 2007, Hewitt made a playful comment stating that the popular song was not about her. During an interview with Entertainment Weekly, she humorously said, "My body is anything but a wonderland. It's more like a pawn shop—a collection of intriguing things put together. If you examine it closely, you might be intrigued, but at first glance, not so much."

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Jessica Simpson

Their relationship lasted from 2006 to 2007, yet it was only in the mentioned 2010 Playboy interview that Mayer publicly acknowledged his attraction to the singer of "With You". According to Simpson's 2020 memoir, Open Book, the two of them remained in contact after the breakup, but she decided to erase his phone number following the revealing Playboy article because she was concerned about her grandmother's reaction.

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Minka Kelly

Mayer and the Friday Night Lights alum were briefly linked in 2007.

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Jennifer Aniston

The guitarist and the former cast member of the popular TV show "Friends" had an on-and-off romantic relationship from 2008 to 2009. He openly admitted to Playboy that during a brief break from Jennifer Aniston, he was intimate with "four or five" other women. However, he expressed regret that things didn't work out with the talented actress. According to a reliable source, as of 2020, the former couple has managed to develop a pleasant and amicable friendship.

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Taylor Swift

Mayer and the country-pop star had a brief relationship from 2009 to 2010. It was rumored that Swift wrote her song "Dear John" based on their unsuccessful romance, a claim that Mayer criticized in an interview with Rolling Stone, calling it "a really disrespectful move" from her side. Swift, however, responded to this accusation by stating, "How presumptuous!" in an interview with Glamour, firmly stating that she never reveals the true inspiration behind her songs. Interestingly, Mayer himself supposedly wrote his track "Paper Doll" in 2013, which was believed to be a response to Swift's song.

Swift's alleged Mayer tracks, speculated to also include songs from Speak Now such as "The Story of Us," "Ours," and "Superman," as well as later tracks like "Would've, Could've, Should've," were met with Swift's attempt to dismiss the discussion at the time. However, the brief relationship between Swift and Mayer once again grabbed attention in July 2023 when Speak Now (Taylor's Version) was released. Prior to that, during one of her Eras Tour stops, Swift urged her fans to approach the situation with kindness and refrain from attacking Mayer. She emphasized this message while introducing "Dear John," stating that she did not release the album to provoke defense on her behalf against someone she may have written a song about a long time ago.

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Katy Perry

The relationship between the member of Dead & Company and the singer of the popular song "Teenage Dream" began in 2012 and ended in 2014. In an interview with Chelsea Handler, Perry mentioned that she had to go through difficult times to find her way in life. However, she made a promise not to discuss her ex anymore, as she didn't want to disrespect him, considering that it has always backfired on her in the past. On the other hand, Mayer revealed to The New York Times in 2017 that his song "Still Feel Like Your Man" was inspired by his relationship with Perry.