Glen Powell Reveals His Biggest Dating Blunder: ‘It Was Gruesome’

Before becoming one of Hollywood’s leading men, Glen Powell weathered his share of awkward dating mishaps.

On the Thursday, Sept. 25 episode of Jake Shane’s podcast, Therapuss, the Hit Man star, 36, recounted one particularly unforgettable night that ended with his date’s nose broken.

“I would do this thing as a kid where I do like skateboard moves. You know where you jump off of something and kinda like spin. You know? Alright, I was not as cool. Like parkour?,” he shared.

“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,” he continued.  

He noted that the whole thing was pretty “gruesome,” as she was “bleeding out” and her face was “puffy.” The whole ordeal ended badly — which Powell said was a prelude for what was to come next.

“And I was like [that] just sort of is like really summed up my love life for the next like while,” said Powell.

Host Shane asked whether Powell was able to recover from such a major blunder, to which the the Topgun: Maverick actor replied that there was no going back after that,

“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,” Powell added.

Despite his early dating mistakes, Powell would go on to date some of Hollywood’s top stars, including Nina Dobrev, Renee Bargh and model Gigi Paris, whom he most recently dated before their split in 2023.

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“They had been on the rocks since Top Gun came out,” a source told PEOPLE at the time. The source also noted that Gigi was never happy with the long-distance filming, and when she came to Australia [where Powell was filming Anyone But You] they both decided to “break up for good.”

However, the breakup did inspire another addition to his life, his dog Brisket, whom he told Entertainment Weekly he got while filming Twisters.

“I was going through a breakup at the time and was in the middle of Enid, Oklahoma, and I had always wanted a dog,” he shared. “It was something I thought about a lot, but it was somewhere in this coffee shop in Enid…. I don’t even know how to describe it, I just had the desire to be a father.”