Turns out John Mayer has a type! And that type is A-list. The Grammy-winning singer-songwriter has dated several celebs over the years, making headlines along the way thanks to some highly messy comments. Take a look back his relationship history–from Jennifer Love Hewitt to Kat Stickler.
Jennifer Love Hewitt: 2002
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John and Jennifer “WHAT ARE YOU WAITING FOR” Love Hewitt dated suuuuper briefly in the early aughts, and there were actually rumors that John wrote his hit “Your Body Is a Wonderland” about her. But not so much!
John confirmed on Call Her Daddy that the song is actually about a high school romance, saying “That was about my first girlfriend. 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.”
“That’s one of those things where people just sort of formed that idea, it gets reinforced over the years, no, no, no,” he added. “I had never met a celebrity when I wrote that song.”
Jessica Simpson: 2006 to 2007
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Jessica and John had a slightly tumultuous on-and-off relationship for about a year, and John said some things that didn’t exactly go down well. Namely, he called Jessica “sexual napalm” in a Playboy interview—which she wrote about in her memoir.
“Again and again, he told me that he was obsessed with me, sexually and emotionally,” she said, adding of their frequent breakups “John loved me when I was shining and he drew inspiration from that light. When he tapped me dry, he looked at me like I was withholding something from him.”
She also slammed him for the whole “sexual napalm” thing, saying “I was floored and embarrassed that my grandmother was actually gonna read that.”
Minka Kelly: 2007 to 2008
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John and Minka dated very briefly—and actually stayed friends after their split! Per People, who reported news of the breakup, “Minka told a couple friends that she and John had broken up but she really didn’t want to tell anyone.”
Jennifer Aniston: 2008 to 2009
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These two met at an Oscars party, and honestly kept things pretty private for most of the relationship. Though, in December 2008, Jennifer did tell told Vogue a bit about their on-again / off-again vibe, saying “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.”
Oh, and after breaking up for good, John somewhat rudely told Playboy (via Us Weekly) “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. I want to dance. I want to get on an airplane and be like a ninja. I want to be an explorer. I want to be like The Bourne Identity. I don’t want to pet dogs in the kitchen.”
Taylor Swift: 2009 to 2010
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John and Taylor dated for just a few months, but the relationship was impactful because Taylor allegedly wrote her iconic song “Dear John” about him. Which…he didn’t exactly handle in the most mature way, complaining to Rolling Stone at length about the song. Ironic since he’s written about multiple exes, but okay!
Katy Perry: 2012 to 2014
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Katy and John had an on-again / off-again relationship, but broke things off for good in February 2014. John wrote the song “Still Feel Like Your Man” about Katy, confirming to 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.”
Meanwhile, back in 2022, Katy had a hilarious reaction when a fan sang a John Mayer song on American Idol, joking “I feel like maybe you should Wikipedia me…I’m triggered!”
FYI, the pair were spotted having a friendly reunion in 2024, so seem to be on good terms!
Kat Stickler: 2025
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Us Weekly reports that John and Kat’s paths recently “crossed online.” Per a source, “John sought her out and pursued her. Kat just broke up with someone she had been dating for a few months and thought it would be fun to date again, and was interested in John.”
Apparently John was “actively pursuing her, inviting her places and texting her often. She is interested and seeing where it goes.” Meanwhile, Kat “doesn’t think this will be a serious relationship” and is just “having fun.”
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