John Mayer’s Notorious Relationship History Includes a Who’s Who of Hollywood A-Listers

There are certain things that come with being a celebrity, and one of the mainstays is having your relationships placed front and center. John Mayer is well-known for his successful music career that has earned him multiple Grammy awards and accolades — but the bulk of the headlines that surround him are due to his long and star-studded dating history.

From the mid-2000s until the mid-2010s, John Mayer’s relationship was a constant topic of conversation, largely due to the information that he shared about them (Jessica Simpson specifically). She was far from the only big name that he romanced, so let’s take a look back at the others.

In 2002, the year after his debut (and Grammy award-winning) album "Room for Squares" was released, John Mayer began dating Jennifer Love Hewitt, and rumors quickly spread that his hit song, “Your Body Is a Wonderland,” was actually about her.

The rumor persisted for several years until December 2022, 20 years after they dated, when John revealed who the muse for the song was while appearing on the Call Her Daddy podcast.

"That was about my first girlfriend,” he clarified, per Entertainment Weekly. “That was about the feeling, which I think was already sort of nostalgic. I was 21 when I wrote that song and I was nostalgic for being 16."

Next up, was his most publicized and documented relationship to date, when he and pop star Jessica Simpson started dating in 2006. Things were very hot and heavy between the two, as she was fresh off of her divorce from Nick Lachey.

However, it was three years after their relationship ended, in 2007, that things reached a fever pitch, courtesy of John’s comments about Jessica in the bedroom — but more on that later.

John moved on pretty quickly and began dating actress Minka Kelly the same year he and Jessica split. The relationship was short-lived, but the two parted as friends, per People.

Not one to stay single for long, John shocked fans when he and Jennifer Aniston made headlines when they started dating after meeting at an Oscar party in 2008.

John later shared his regrets that the pair’s relationship didn’t last. "I’ll always be sorry that it didn’t last. In some ways, I wish I could be with her. But I can’t change the fact that I need to be 32,” he told Playboy, per Us Weekly.

A pair of music divas followed, with John dating both Taylor Swift (from 2009 to 2010) and Katy Perry, on/off from 2011 until 2014. His relationship with Taylor spawned her song “Dear John,” while Katy inspired him to write “Still Feel Like Your Man.”

He confirmed that Katy was the muse for the song in an interview with the New York Times. "Who else would I be thinking about? And by the way, it's a testament to the fact that I have not dated a lot of people in the last five, six years. That was my only relationship. So it's like, give me this, people," he said at the time.

In a 2010 interview with Playboy, John introduced a new term to the world when he referred to Jessica as “sexual napalm.”

When asked about how he felt at the time about the high-profile nature of their relationship, specifically as it related to endless paparazzi coverage, he provided a shocking and uncomfortable response.

"It wasn't as direct as me saying, 'I now make the choice to bring the paparazzi into my life.' I really said, 'I now make the choice to sleep with Jessica Simpson,'" he told the outlet.

"That was stronger than my desire to stay out of the paparazzi's eye," John said. "That girl, for me, is a drug. And drugs aren't good for you if you do lots of them. Yeah, that girl is like crack cocaine to me. ... Sexually it was crazy. That's all I'll say. It was like napalm, sexual napalm."

Naturally, Jessica did not appreciate his comments and expressed her feelings while speaking with Oprah Winfrey. "I tried to read the article and I was so ... I was so disappointed in him. ... It made me so sad. And it was really discouraging because that's not the John that I knew," she said.

She discussed the incident in even more detail in her 2021 memoir, Open Book.

John is currently rumored to be dating social media influencer Kat Stickler.