John Mayer’s career has always been as much about feeling as it is about finesse. When he dropped “Room for Squares” in the early 2000s, you could already tell this Connecticut-born guitar nerd wasn’t just another guy with a six-string and a daydream. There was emotional weight and melancholy even in his poppiest hooks, balancing technical skill with a relatability that made songs like “No Such Thing” and “Your Body Is a Wonderland” almost impossible to resist.
The thing about Mayer is, he’s never seemed totally at ease with the circus that comes with stardom. He definitely had his wild spells – tabloid headlines, oversharing in interviews, run-ins with celebrity culture – but in the past decade or so, he’s settled into a mellower version of himself. There’s an awareness now, a sense that he’s learned (sometimes the hard way) when to step out into the spotlight and when to retreat. That tension between wanting to connect and wanting to stay private seems to seep into his songwriting, too – albums like “Continuum” and “Born and Raised” sound like conversations you might have with an old friend at 2 a.m.
Now, ask most casual music fans about Mayer and you’ll likely hear as much about his romantic life as about his guitar solos. For better or worse, his run-ins with other celebrities have become pop culture footnotes.
His relationship with Katy Perry is probably the most high-profile from recent years. They dated off and on between 2012 and 2015, even collaborating on the dreamy “Who You Love.” After they broke up, both talked about the relationship with a kind of respectful nostalgia – no public feuding, no messy tell-alls, just a mutual recognition of what they had.
The rest of his dating history reads like a snapshot of 2000s and 2010s celebrity culture: Jennifer Aniston for a spell (and a lot of tabloid speculation), Jessica Simpson in what seems to have been a passionate but stormy romance, and of course, Taylor Swift. Swift’s “Dear John” is widely considered to be about Mayer, who later admitted the song stung: “It was a really lousy thing for her to do,” he told Rolling Stone, though he’s never been one to shy away from addressing his own role in breakups, at least musically.
Other rumored relationships pop up now and then – Kiernan Shipka, Natalie Morales – but whether or not there was any real fire behind those rumors, Mayer, these days, is much less of a fixture in gossip columns than he once was.
It’s impossible to separate these stories from his music. Songs like “Slow Dancing in a Burning Room” and “Still Feel Like Your Man” (which he’s candid enough to admit is about Perry) are proof that Mayer wears his heart – and mistakes – on his sleeve. He told Rolling Stone back in 2010, “I’m actually very, very honest in relationships.” That honesty sometimes got him in trouble, especially in the early days when he had a knack for saying a little too much. But it’s also the thing that pulls people into his songs: they feel like confessions, guideposts from someone still figuring it all out.
Past Relationships
Kiernan Shipka
Natalie Morales
Katy Perry
Kim Kardashian
Reena Hammer
Taylor Swift
Scheana Shay
Jennifer Aniston
Minka Kelly
Jessica Simpson
Milana Vayntrub
Rhona Mitra
Jennifer Love Hewitt
Vanessa Carlton
After more than two decades in the public eye, Mayer remains hard to pin down – sensitive, self-aware, occasionally self-sabotaging. He’s matured, both musically and personally, but hasn’t completely shed the restless searching that made him interesting in the first place. And while his love life might always be a subplot in the story, it’s Mayer’s willingness to document his own flaws, heartaches, and small victories that keeps fans coming back, album after album.
