Even Hollywood stars have those cringe-worthy dating moments that stick with them forever.
Glen Powell, 36, opened up about one of his most unforgettable—and unfortunate—romantic mishaps on Jake Shane’s Therapuss podcast, recalling a teenage accident that left his date with a broken nose.
The Skateboard Stunt That Went Horribly Wrong
Powell explained that, as a teenager, he loved doing skateboard-style stunts—jumping, spinning, and trying to show off “parkour” moves.
“I was doing skateboard parkour, didn’t realize my date had followed behind me, and I spun and I knocked her… I elbowed her in the face and I broke her nose,” he recalled.
Describing the scene as “gruesome,” Powell said his date was bleeding and her face quickly became puffy.
Looking back, he joked that the incident perfectly summed up his love life at the time.
No Chance to Salvage the Date
When podcast host Jake Shane asked if there was any way to save the date, Powell was brutally honest. “No, no, no. There’s nothing to do.
You ruined it in so many ways.
She’s trying to play it off, and it was really not good,” he admitted.
Despite this early stumble, Powell has since been linked to several high-profile women, including actress Nina Dobrev, TV host Renee Bargh, and model Gigi Paris, his most recent relationship before their 2023 split.
An Awkward Hollywood Encounter
Powell also shared a story about an uncomfortable encounter with a celebrity who had recently been “canceled.”
He described arriving at a Hollywood party and initially feeling excited to meet one of his favorite stars.
“I showed up to the party, and there was somebody that had been on the ropes in terms of getting canceled… I was like, ‘Oh, dude, such a big fan,’” he said.
The mood shifted when a photographer asked them to pose for a picture. Powell said he realized it wasn’t a good idea to be seen with this celebrity.
“I realized very quickly—I was like, ‘Ooh, I don’t know if this is a good idea,’” he admitted, noting that the person “clearly clocked” his hesitation.
Thoughts on Cancellation and Accountability
Reflecting on the situation, Powell drew a comparison to a character he plays, Russ Holliday, a football star who gets canceled but is ultimately not a bad person. “Russ Holliday is just a guy that made a mistake.
He’s not a bad guy. Some of these other people that get canceled, they should lie where they’re shot,” Powell said, keeping the celebrity’s name private.
Fans Already Speculating
Although Powell didn’t name the star, fans have already launched a guessing game online, with names like Johnny Depp, Armie Hammer, Chris Pratt, Ezra Miller, Will Smith, and Russell Brand being tossed around.
Powell has yet to respond to the speculation, and representatives have not commented.