Who Has John Mayer Dated? What Really Happened with the Guitar Legend

Honestly, if you grew up in the 2000s, you couldn't escape the headlines. John Mayer wasn't just the guy singing about your body being a wonderland; he was the guy on every tabloid cover, usually with an A-list actress or a pop star on his arm. But lately? It’s been quiet. Kinda weirdly quiet for a man who once basically treated the paparazzi like a personal film crew.

People always ask: who has John Mayer dated? It’s a long list. It’s a complicated list. And if you ask some of his exes, it’s a list that comes with a lot of baggage and a few hit songs.

The Early Days and That Infamous "Wonderland" Rumor

Before he was the "sexual napalm" guy, John was just a rising blues-pop guitarist. His first real public romance was with Vanessa Carlton back in 2002. They were both at the top of the charts—she had "A Thousand Miles," he had "No Such Thing." It was short, sweet, and mostly under the radar.

Then came Jennifer Love Hewitt.

This is where the mythology starts. Everyone assumed "Your Body Is a Wonderland" was about her. She’s actually denied it, once joked her body was more like a "pawnshop" than a wonderland. They only lasted a few months, but it set the template for Mayer’s future: high-profile, high-intensity, and highly scrutinized.

The Chaos of the Jessica Simpson Era

If you want to know what really changed John Mayer’s public image, you have to look at Jessica Simpson. This wasn't just a fling. It was a 2006-2007 whirlwind that Jessica later described in her memoir, Open Book, as an emotional rollercoaster.

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She wasn't holding back.

Jessica wrote about how she felt she had to "win" every conversation with him. She even had friends check her texts for grammar because she was so scared of looking "dumb" in front of him. They broke up and got back together something like nine times. It was messy. It was toxic. And it culminated in that 2010 Playboy interview where John called her "sexual napalm."

That quote effectively ended their relationship for good. It also started John's "villain arc" in the eyes of the public.

The Jennifer Aniston and Taylor Swift Chapters

In 2008, John started dating Jennifer Aniston. They met at an Oscars party. On paper, it was the ultimate Hollywood power couple. In reality? He was 30, she was 39, and he was obsessed with Twitter (back when it was new). He famously told Playboy that their age gap was a factor, saying he "needed to be 32."

Aniston, being the class act she is, later told Vogue that he was a "wonderful guy" but admitted the way he handled the breakup publicly was... let’s say, unnecessary.

Then, the big one. Taylor Swift.

They dated from late 2009 to early 2010. She was 19; he was 32.
It resulted in:

• "Dear John" (Taylor’s scathing takedown).
• "Paper Doll" (John’s rumored response).
• A decade of "Swifties" hating John Mayer.

John later called "Dear John" "cheap songwriting," but the damage was done. The "predatory" narrative around the age gap has followed him ever since, especially with the release of Speak Now (Taylor’s Version) in 2023.

Katy Perry: The Last "Big" Public Relationship

From 2012 to 2015, John and Katy Perry were the "it" couple of the music world. They did a duet, "Who You Love," and they actually seemed... happy? They were on and off, but John later admitted his song "Still Feel Like Your Man" was about her.

He told the New York Times in 2017: "Who else would I be thinking about?"

Since Katy, John has mostly stayed out of serious, public relationships. He’s been linked to people like Kiernan Shipka (which sparked more age-gap discourse) and most recently, in late 2025, influencer Kat Stickler.

Reports say he "sought her out," and they’ve been seen grabbing dinner at the Flyfish Club in New York. Whether it’s a serious thing or just "having fun," it’s the most action his dating life has seen in years.

What This Means for You

If you're following John Mayer’s dating history, the takeaway is pretty clear: he’s evolved from a guy who couldn't stop talking to the press to a guy who values a much tighter circle. He’s admitted in interviews that he still wants to get married, but the "rockstar" dating style of the 2000s is clearly behind him.

To keep up with the latest on his current status with Kat Stickler or any new music drops, keep an eye on his "Life with John Mayer" SiriusXM channel. He’s much more likely to drop a hint there than in a tabloid interview these days.