It seems Diplo just can’t escape a good celebrity moment — especially when it involves two people he’s claimed to have a “past” with.
The 46-year-old DJ raised eyebrows after sharing a playful selfie alongside singer Katy Perry and former Canadian Prime Minister Justin Trudeau on Monday night — the very two stars he once joked about dating.
A Playful Throwback and a Cheeky Caption
The snapshot, posted to his Instagram, showed Diplo grinning beside Trudeau, while Perry, sporting her recognizable cropped blonde hair, appeared to walk right into the frame behind them — completely unaware she’d photobombed the shot.
With his usual cheeky humor, Diplo captioned it: “The one that got away.”
It wasn’t long before fans made the connection — this was the same look Perry had back in 2017, during her early relationship days with actor Orlando Bloom.
The photo was originally taken years ago at a formal event when Trudeau was still serving as Canada’s twenty-third Prime Minister.
Diplo’s Surprising Claims on a Podcast
The DJ’s nostalgic post came just hours after his appearance on the Smart Girl Dumb Questions podcast, where he made a lighthearted but eyebrow-raising claim.
While chatting about Perry’s rumored romance with Trudeau, Diplo quipped, “And now Katy Perry is dating Justin — pretty fire.”
When the host started to mention others who had dated Perry, Diplo interrupted with a smirk, “Dated Katy Perry, like me?” before adding, “I did.”
Then, keeping the playful tone going, he said, “I did date Trudeau too.
That was a weird one though. I’m not really into politicians.”
The podcast team quickly clarified later that Diplo was joking about dating Trudeau — though his brief fling with Perry back in 2014 was very real.
That Short-Lived Spark with Katy Perry
Rumors of Diplo and Perry’s romance first surfaced in 2014 when the two were spotted out and about in New York City.
While some insiders insisted they were “just friends,” others described them as more than that, saying their connection was instant and filled with chemistry.
“They got along really well,” one source told E! News at the time. “He’s just a fun guy and he makes her laugh.
They met while talking about working on music together, but things clicked right away.”
Katy Perry’s Relationship with Justin Trudeau Confirmed
Now, years later, the story has taken a twist. Perry herself confirmed her budding romance with Trudeau during a concert in Prague last Thursday.
When a fan once again proposed to her from the audience — ring in hand — the singer had to laugh and set the record straight.
“This guy is trying to get me to marry him and he has a ring in his hand,” she told the crowd.
“No! I’m dating someone else, for crying out f*****g loud!”
Her comment, caught on fan videos and shared across TikTok, confirmed what many suspected — her relationship with the former Prime Minister is real and very much happening.
From Prague to Paris — A Public Romance Blossoms
Perry and Trudeau first sparked dating rumors back in July after being seen together at Montreal’s upscale restaurant Le Violon.
Since then, the pair have been spotted on several outings, most recently celebrating Perry’s 41st birthday in Paris.
It marks a new chapter for both — Perry, who recently split from actor Orlando Bloom after years together, and Trudeau, who ended his marriage to Sophie Grégoire in 2023.
Two Worlds Collide
It’s not every day a pop superstar and a former world leader become an item, but Perry and Trudeau seem to have found a connection that’s caught the world’s attention.
As for Diplo, the ever-unbothered DJ appears to be taking it all in stride — laughing at the coincidence of sharing the frame with two people who’ve both, in one way or another, crossed his past.