Welcome to Crush of the Month Club, where I spotlight the famous men who are unexpectedly stealing our attention (or maybe just mine!). Maybe it’s their charm, their talent, their confidence — or maybe it’s just good hair, and BDE. Either way, this is a space to appreciate the crushes we didn’t see coming (or the ones we did).
Where do I even begin? John Mayer is my original, forever, ride-or-die crush. I’ve had my eyes (and ears) on him since my early twenties — and I mean really early twenties. Back when “Your Body is a Wonderland” was playing in dorm rooms and I was daydreaming of front-row seats. Which, yes, I scored…twice. One time at a super small venue, Housing Works Bookstore in NYC, surrounded by like 50 people, after winning tickets as a dedicated fan club member (yes, I was in his fan club) where I swear he sang his signature ballad straight to me.
Another time I bid on eBay (back in the day!) just to see him up close in Montreal. Actually, I think I did that twice — once for Montreal, another time for Toronto (I’ve seen him three times in Toronto).
Not surprisingly, I’ve watched John Mayer the most in concert than any other artist — I think it’s up to ten times now, with the latest being in Vancouver back in 2023.
And that’s not all — I even wrote a play about him. Literally. It went to the Hollywood Fringe Festival in 2010 and — can you guess what it was about? Naturally, it was all about him falling for me, his teenage-sweetheart-turned-soulmate after that infamous Playboy interview when he needed some serious image rehab. I was like, “I GOT YOU, JOHN!” (ooh, boy. I had zero chill back then.)
And yes, I’ve met him! IN PERSON. Well, kinda. It happened at the Comedy Cellar in New York where I worked as a waitress out of of NYU, back in 2006. My mom had jokingly predicted I’d run into him there one day and — poof — there he was. John Mayer, taller than life. I was too starstruck to say anything, so we just stared at each other and that was that.
Sigh.
So why John Mayer?
I guess there’s a quiet brilliance to him — he’s articulate, funny, and has that smoldering charm that only grows with age.
And even though he’s super famous, he’s also surprisingly private these days. Long gone are the days of his overly candid (and often controversial) interviews; now he’s more selective and mysterious. Does that make him even hotter? Absolutely.
Here’s why John Mayer is my July Crush of the Month (and definitely in my Crush Hall of Fame).
Name: John Mayer
Age: 47
Astrological Sign: Libra
Location: Montana/NYC/LA — wherever the music takes him
Occupation: Musician, songwriter, occasional stand-up comic, modern-day troubadour
Height: 6’3” (I can verify he’s tall!)
John Mayer is like if you took a brooding, hyper-verbal heartthrob and trained him to shred guitar like his feelings depended on it. He’s casually intense, endlessly charming, and gives off serious “misunderstood poet with a secret soft side” energy — the kind who’d write you a song, say it’s “no big deal,” and then drop it at midnight like it wasn’t an emotional bomb. (And then look at you like, well? swoon…)
He’s been making waves in the music world forever — Grammy wins, sold-out tours, a Current Mood radio show — but what really sets him apart (besides, you know, that voice, those hands, the tattoos, and that face that looks like it was carved in marble) is his self-awareness. Whether he’s spilling tea about his personal growth, owning up to his mistakes in interviews, or just being hilariously candid on basically every interview, Mayer’s honesty feels like a secret club you want to be part of.
He’s been real about his messy past — the interviews he regrets, the relationships that made the tabloids — and these days seems genuinely focused on evolving. In a world where most celebs craft squeaky-clean personas, that kind of messy authenticity is sexy. Vulnerability? It’s giving.
Hobbies & Interests
Playing guitar like an absolute master — seriously, if you haven’t seen him live, do it.
Touring the world and jamming with other top-notch musicians, like The Grateful Dead.
Being hilariously dry on Instagram and making surprise comedy cameos.
Hanging out with his bestie Andy Cohen — especially on NYE broadcasts.
Collecting watches, crafting guitars, geeking out over sound equipment.
Getting deep into his thoughts about life, relationships, and creativity — sometimes a little too deep!
What He’s Looking For
Probably someone who can keep up with him intellectually and creatively.
Rumoured to want a serious relationship and “wife,” even though his dating history looks more like a string of passionate, famous flings. But people can change!
Chemistry matters —and if you pass that Gravity-level pull? Lucky you.
Someone who enjoys life but is also fine with him being on tour and spending time on his art.
Potential Red Flags
Serious commitment-phobe vibes: he says he wants a wife, but… still single at 47. (Maybe he just hasn’t found The One yet? #hi)
Reputation as a heartbreaker — long list of famous exes like Taylor Swift, Jessica Simpson, Jennifer Aniston, and Katy Perry.
Might secretly believe he’s the smartest person in the room — and honestly, he might be right.
Known for past controversial remarks (hello, Playboy interview), even if that’s mostly behind him.
Rumored to lean into the “casual sex” lifestyle (hence the “Safe Sex” label on Deux Moi). Hey — at least he’s safe!
Keeps his personal life so guarded now that you might never really know him.
Why He’s Our Crush of the Month
There’s something endlessly intriguing about John Mayer. Maybe it’s that voice that melts into your bones, or those soulful guitar riffs that never get old. Maybe it’s that he’s matured into someone who keeps things more low-key and intentional — a stark contrast to his former tabloid self.
And sure, he’s probably a lot to handle. But there’s also a softer, wiser guy under all that — someone who still writes gorgeous songs, someone who says he’d like to settle down.
Safe sex? Definitely. A potential rebound? Absolutely. Pure entertainment? Always.
Here’s to you, John Mayer — forever Crush of the Month. 🎸💛
Would you swipe right?
I mean…of course. I’d love to go out on a first date. I think the conversation would be endlessly fascinating. As for anything beyond that…well, my favourite song IS “Slow Dancing in a Burning Room” (and while I know that song is about breaking up, it is by far the sexiest song).
Anyway. After 20 years of crushing…I’ll say, Message me, John — let’s see if you’re ‘Still Feel Like My Man.’ LOL.
Thanks for being here!
Love, Brie xoxo
P.S. Let me know if you agree!! Or Leave a comment on who your crush of the month is!
I will always be a JM fan!! And I appreciate how gracefully he is aging into a wise elder sort of guy. He's so smart and funny, it's scary. I'm glad he is thinking more before he speaks. I wish sometimes that his music would better reflect his humor and whimsy.