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John Mayer has a star-studded relationship roster.
The “Gravity” singer is known for dating high-profile women like Katy Perry, Jennifer Aniston and Taylor Swift.
While he has never tied the knot, Mayer has expressed his desire to get married one day.
“I would not date someone if it didn’t have the upward mobility of becoming a marriage,” John said at a live event for the “SmartLess” podcast in June 2025. “Every girlfriend would be a potential wife at this point.”
At the time, Mayer claimed that he was “absolutely” ready to be a husband.
In October 2025, Mayer sparked dating rumors with influencer Kat Stickler — leading many to wonder whether he was finally settling down.
Keep reading to look back at Mayer’s dating history, from his serious relationships to casual flings.
Jennifer Love Hewitt: 2002
The songwriter sparked dating rumors with Jennifer Love Hewitt after the pair were spotted holding hands while out in public in 2002.
At the time, rumors swirled that Mayer wrote his 2002 hit, “Your Body is a Wonderland,” about the “Heartbreakers” actress.
However, Mayer confirmed on the “Call Her Daddy” podcast in 2022 that the song was actually inspired by his high school girlfriend.
Jessica Simpson: 2006 to 2007
Mayer and Jessica Simpson entered into what appeared to be a hot and heavy relationship in 2006.
The musician infamously described the “Irresistible” singer as his “sexual napalm” in an interview with Playboy.
“That girl … is like crack cocaine to me … Sexually it was crazy. That’s all I’ll 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,” sharing that they broke up about nine times before finally ending things for good after just one year.
“We were great at intimacy,” the pop star wrote. “We were great at loving each other. That was easy, but the relationship was very complex.”
Mayer, for his part, said he had no plans to read her book — though he did admit to seeing some excerpts.
Minka Kelly: 2007 to 2008
Minka Kelly and John Mayer had a short-lived romance in 2007.
They were seen looking loved-up at several public events before ending things after a year.
Despite their breakup, a source told People at the time that they were “still friends.”
Jennifer Aniston: 2008 to 2009
Mayer first crossed paths with Jennifer Aniston at an Oscars party in 2008 and they started seeing each other shortly after that.
They kept their relationship relatively out of the spotlight until their breakup a year later.
However, the “Friends” star did touch on their split in a December 2008 Vogue interview, admitting, “We care about each other.”
“It’s funny when you hit a place in a relationship and you both realize, we maybe need to do something else, but you still really, really love each other. It’s painful,” she added.
Taylor Swift: 2009 to 2010
The Dead & Company guitarist and Taylor Swift struck up a romance in 2009.
They initially bonded after collaborating on his 2009 song “Half of My Heart” and dated for a few months after that.
Their relationship even inspired the lyrics to Swift’s 2010 song, “Dear John.”
“Dear John, I see it all now, it was wrong / don’t you think 19 is too young to be played by your dark twisted games,” Swift sang in part, referring to how she was 19 and he was in his 30s when they dated.
Mayer didn’t seem to appreciate the track, calling it “cheap songwriting” in an interview with Rolling Stone.
Katy Perry: 2012 to 2014
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Mayer moved on from Swift with the “Love Story” singer’s longtime foe, Katy Perry, in 2012.
He and the “Dark Horse” singer dated on and off for two years until breaking up in 2014.
Mayer reflected on their love in his 2017 song, “Still Feel Like Your Man,” singing, “Still think I’m never gonna find another you.”
He confirmed to the New York Times that the song was indeed about Perry, sharing, “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.”
Ten years after their split, the exes were seen having a friendly conversation at Sabrina Carpenter’s Short n’ Sweet Tour show in Los Angeles in 2024 — signalling that there’s no bad blood between them.
Kat Stickler: 2025
Rumors started swirling in October 2025 that Mayer and Kat Stickler were an item.
A source confirmed to US Weekly that they had been hanging out but were “still very new.”
“He has been actively pursuing her, inviting her places and texting her often,” the source divulged.
The content creator went on a date with Mayer after a recent breakup because she allegedly “thought it would be fun to date again.” Stickler is reportedly open to “seeing where it goes” but “doesn’t think this will be a serious relationship.”
Mayer and Stickler set tongues wagging after they were spotted grabbing dinners at two separate members-only clubs.
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