John Mayer has a star-studded roster of romantic relationships.
The “Gravity” singer is known for dating famous women like Katy Perry, Jennifer Aniston, and Taylor Swift.
Mayer has never been married, but has expressed a desire to marry someday.
“I wouldn’t date someone if I didn’t have the upward mobility of marriage,” John said during a June 2025 live event on the podcast “SmartLess.” “At this point, any girlfriend would be a potential wife.”
At the time, Mayer claimed he was “absolutely” ready to become a husband.
In October 2025, Mayer sparked dating rumors with influencer Kat Stickler, leading many to wonder if he was finally starting to settle down.
Read on to take a look back at Mayer’s dating history, from serious relationships to casual flings.
Jennifer Love Hewitt: 2002
In 2002, rumors of a relationship with songwriter Jennifer Love Hewitt surfaced after the two were seen holding hands in public.
At the time, rumors circulated that Mayer wrote his 2002 hit song “Your Body is a Wonderland” about the “Heartbreakers” actress.
However, Mayer admitted on his 2022 podcast Call Her Daddy that the song was actually inspired by his high school girlfriend.
Jessica Simpson: 2006-2007
Mayer and Jessica Simpson entered into what seemed like a hot and heavy relationship in 2006.
The musician infamously described the “Irresistible” singer as a “sexual napalm” in an interview with Playboy.
“That girl…was like crack cocaine to me…sexually crazy. That’s all I can say. It was like napalm, sexual napalm,” he told the magazine in 2010.
However, Simpson later opened up about the toxicity of their relationship in her 2020 memoir Open Book, revealing that they broke up about nine times and finally called it quits for good after just a year.
“We were good at being intimate,” the pop star wrote. “We were good at loving each other. It was easy, but the relationship was very complicated.”
Mayer said he had no plans to read her book, but admitted he had seen some excerpts.
Minka Kelly: 2007-2008
Minka Kelly and John Mayer had a short-lived romance in 2007.
They appeared loved up at several public events until they settled a year later.
Despite their breakup, a source told People at the time that they were “still friends.”
Jennifer Aniston: 2008-2009
Mayer first met Jennifer Aniston at a 2008 Oscar party and they began dating soon after.
They kept their relationship relatively out of the spotlight until they broke up a year later.
However, the “Friends” star addressed the breakup in a December 2008 interview with Vogue, admitting, “We care about each other.”
“The funny thing is, even though the relationship stalled and we both realized we needed to do something else, we still really, really love each other. That’s tough,” she added.
Taylor Swift: 2009-2010
The Dead & Company guitarist and Taylor Swift began their romance in 2009.
The two met in 2009 after collaborating on his song “Half of My Heart,” and dated for several months after that.
Their relationship also inspired the lyrics of Swift’s 2010 song “Dear John.”
“Dear John, I know it all now, it was a mistake / Don’t you think 19 is too young to play in your dark, twisted games,” Swift sings in part, referring to their date when she was 19 and he was in his 30s.
Mayer did not seem to appreciate the song, calling it “cheesy songwriting” in an interview with Rolling Stone magazine.
Katy Perry: 2012 to 2014
Mayer split from Swift in 2012 and signed with Katy Perry, the “Love Story” singer’s longtime nemesis.
He and the “Dark Horse” singer dated on and off for two years before breaking up in 2014.
Mayer reflected on their love in his 2017 song “Still Feel Like Your Man,” singing, “I think I’ll never find you yet.”
He confirmed to the New York Times that the song was indeed about Perry, saying, “Who else are you thinking about? And, by the way, this is also a testament to the fact that I haven’t dated too many people in the last five or six years. That’s been my only relationship. So I’m like, give me this.”
Ten years after their breakup, the former lovers were spotted having a friendly conversation at Sabrina Carpenter’s Short and Sweet Tour show in Los Angeles in 2024, suggesting there is no bad blood between them.
Kat Stickler: 2025
Rumors began flying around in October 2025 that Mayer and Kat Stickler were an item.
A source confirmed to US Weekly that although they had been playing together, they were “still newbies.”
“He is actively pursuing her, inviting her to places and texting her frequently,” the source revealed.
The content creator allegedly dated Mayer after their recent breakup because she “thought it would be fun to date again.” Stickler is reportedly willing to “see what happens,” but “doesn’t think this will be a serious relationship.”
Mr. Mayer and Mr. Stickler caused a stir when they were spotted having dinner at two separate members’ clubs.
Shortly after she and Mayer made headlines, Stickler confirmed she was single in a cheeky TikTok post.
