You probably didn’t have this on your pop culture bingo card back in the late 2000s.
It sounds like a Mad Libs result. The operatic "You Raise Me Up" baritone and the girl who kissed a girl and liked it? Honestly, it feels like a glitch in the Hollywood simulation. But here we are in 2026, and the story of Josh Groban and Katy Perry remains one of the most low-key fascinating chapters in celebrity dating history.
It wasn’t a messy tabloid explosion. There were no public screaming matches or dramatic "it's over" Instagram posts—mostly because Instagram barely existed when they were a thing. Instead, what we have is a slow-burn revelation that took nearly a decade to fully come to light.
The Secret 2009 Timeline
Let's wind the clock back to 2009. Katy Perry was just exploding into a global phenomenon. Josh Groban was already the darling of the adult contemporary world. They met before Perry’s career really hit the stratosphere.
For years, nobody really knew what was going on between them. They were "friends." They were "hanging out." In a 2013 interview with Details magazine, Groban was pretty cagey about it. He used a phrase that only a polite theater kid would use, saying they "skated on the line of dating."
What does that even mean? It sounds like a very intense game of friendship chicken.
Later, on Watch What Happens Live, Groban finally stopped the wordplay. He admitted to Andy Cohen that they did, in fact, date. "We were both very private," he explained. They realized they functioned better as friends, and according to both of them, they’ve stayed close ever since. It’s actually kind of refreshing. In an industry built on bridge-burning, they just... decided to be cool.
Is He Actually "The One That Got Away"?
The internet basically broke in 2017 during Katy Perry’s 72-hour Witness World Wide livestream. While she was doing a "Spill Your Guts" segment with James Corden, she had to rank her ex-boyfriends.
John Mayer, Orlando Bloom, Diplo—the usual suspects.
But then she dropped the bomb. She pointed to Josh Groban and called him "the one that got away."
People were stunned. Suddenly, the lyrics to her 2010 hit "The One That Got Away" were being scrutinized like the Zapruder film. Was the guy in the song—the one with the Mustang who listens to Radiohead—actually the guy who sings "You Raise Me Up"?
Josh Groban’s reaction was pure gold. He told Andy Cohen that he was watching the livestream and literally did a "double take and a spit of my coffee."
The Lyrics vs. Reality
If you look at the song, the math doesn't quite add up. Groban was the first to point this out. He told reporters that while he was flattered, he had some notes on the accuracy:
- The Mustang: Groban says he never owned one.
- The Tattoos: He’s famously ink-free.
- The Vibe: The song feels very "indie-rock summer love," while their actual relationship seemed to be two "goofballs" (his words) hanging out in private.
Katy later clarified that the song is more about the feeling of a lost connection rather than a literal biographical account of Groban's life. It’s the "what if" that haunts you.
Why This Pairing Actually Made Sense
On paper, they are opposites. She's high-energy pop kitsch; he’s classic, polished, and safe. But if you look at their personalities, the "goofball" factor is the glue.
Katy Perry has always had a quirky, almost vaudevillian sense of humor. Josh Groban is secretly one of the funniest people in music—check his old Twitter threads or his cameos in It's Always Sunny in Philadelphia. They both have this self-deprecating streak that likely made them a perfect match behind closed doors, away from the prying eyes of 2009 paparazzi.
They were young. They were both navigating sudden, massive fame. Sometimes the person who "gets away" isn't the one who broke your heart, but the one you met when life was just too chaotic to make it work.
What We Can Learn From the Groban-Perry Dynamic
The most impressive part of the Josh Groban and Katy Perry saga isn't the dating itself. It's the aftermath.
How many celebrities can call their ex "the best" and mean it? There is a level of maturity here that is rare in Hollywood. They didn't use their "line-skating" to sell albums or grab headlines at the time. They kept it to themselves until it was old news, which gave it a layer of authenticity that PR-managed couples usually lack.
If you’re looking for drama, you won't find it here. What you'll find is a story about two people who genuinely liked each other, tried to make a romance work, failed, and decided that the friendship was too valuable to toss in the trash.
Actionable Insights for Your Own "What Ifs"
- Audit your "ones that got away": Are you mourning the person or the version of yourself you were when you were with them? Katy’s song is about nostalgia, not necessarily a desire to get back together.
- Prioritize the friendship: If a relationship is "skating the line," sometimes it's better to step back onto the "friend" side before you ruin the connection entirely.
- Keep it private: Groban and Perry stayed under the radar, which is likely why they can still be friends today. Not every life update needs to be public.
Look at where they are now. Katy is with Orlando Bloom, and Josh has moved on with his own long-term relationships. They’re happy. But that doesn't mean they can't occasionally look back at 2009 and wonder "what if" over a cup of coffee. Just don't expect Josh to buy a Mustang anytime soon.
To dive deeper into the history of these artists, you can check out their respective discographies from the Teenage Dream and Illuminations eras, which provide the sonic backdrop to this brief but meaningful Hollywood crossover.