Joshua Goldman
Joshua Goldman
min read · September 28, 2025 · Entertainment

Glen Powell's 'Gruesome' Skateboard Date Gone Wrong: How a Spin Move Broke a Nose

Glen Powell opened up about one of his most unforgettable, and painful, dating mishaps

Glen Powell's Dating Disaster: The Actor Opens Up About a Painful Breakup and a Scandalous Encounter with a Cancelled Celeb

In a jaw-dropping episode of Jake Shane's Therapuss podcast, Glen Powell, the 36-year-old star of Top Gun: Maverick, dished out about one of his most cringe-worthy dating experiences. The Hollywood heartthrob revealed that he once accidentally broke his date's nose with an ill-fated skateboard move.

It all went down when Powell was just a teenager. "I would do this thing as a kid where I'd jump off something and spin, like parkour," he explained on the podcast. "So, 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."

On Thursday's episode of Jake Shane's Therapuss podcast, the Hit Man star, 36, admitted that an ill-timed move on his part once left his date with a broken nose

The gruesome incident left his date bleeding profusely, with a face that quickly became puffy. Powell couldn't help but joke about how this mishap set the tone for his love life at the time. "And I was like [that] just sort of is like really summed up my love life for the next like while," he quipped.

When host Shane asked if there was any way to salvage the date, Powell delivered a hilarious roast of himself: "No, no, no. I mean there's nothing to do. You ruined it in so many ways. She's, like, trying to play it off and it was, like, really not good."

Despite this early stumble, Powell has since been linked to several high-profile women, including the stunning Nina Dobrev, TV host Renee Bargh, and model Gigi Paris, his most recent flame before their 2023 split.

When host Jake Shane asked if there was any chance to salvage the date, Powell didn't hesitate. 'No, no, no. I mean there's nothing to do'

But that's not all - Powell also shared a shocking story about an encounter with a celebrity who had recently been canceled. He described how he was caught off guard when the unnamed star approached him at a party.

"I showed up to the party and there was somebody that had been on the ropes in terms of getting canceled," Powell revealed. "It was one of those Hollywood parties where there's like cameras and press and all that stuff."

Initially, he was thrilled to meet his favorite celebrity: "This person had made some of my favorite movies and I was like, 'Oh, this is great.' He came up and he said, 'Nice to meet you.' I was like, 'Oh, dude. Such a big fan.'"

During the interview, Powell also spoke about an uncomfortable Hollywood encounter with a celebrity who had recently been 'canceled'

However, the mood shifted when a photographer asked them to pose together. Powell explained: "This person was recently canceled and it was not good. I was a fan of their work but not a fan of their choices. So, I was kind of just being nice."

But then, things took a turn for the worse. Powell revealed that he quickly realized his hesitation had been "clocked" by the actor. "I realized this guy's face is toxic," he said. "Going out into the world, people are having a visceral reaction to this person in terms of the bad choice they've made."

In an interesting twist, Powell drew a comparison to his character Russ Holliday from Chad Powers, who gets canceled and disguises himself to join another team: "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."

Despite the early stumble, Powell has since been linked to several high-profile women, including model Gigi Paris, his most recent relationship before their 2023 split; seen in 2023

Fans are now speculating about the identity of the celebrity involved, with names like Johnny Depp, Armie Hammer, Chris Pratt, Ezra Miller, Will Smith, and Russell Brand being thrown into the mix.

The Top Gun: Maverick star has yet to respond to the speculation. When reached out by thescholarlynote.com for a comment, Powell's representatives remained tight-lipped.

As fans continue to guess who might be behind this scandalous encounter, one thing is clear - Glen Powell is never short on stories and always keeps it real, even when it comes to his most cringe-worthy moments.