Glen Powell, known for his role in Hit Man, recounted an unforgettable and painful experience from his early dating life on Jake Shane’s podcast Therapuss on September 25. The actor, now 36, shared how a teenage stunt during a date resulted in a broken nose and significant injury, marking a disastrous start to his romantic endeavors. This Glen Powell first date accident left a lasting impression on his love life.
Powell reminisced about his youthful tendency to perform daring stunts, which he jokingly called “skateboard parkour.” He explained,
“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?”
The thrill-seeking behavior unexpectedly led to disaster when he accidentally hit his date in the face during one such move. He revealed,
“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,”
a moment he described as quite gruesome.
The actor detailed how his date ended up bleeding heavily, with a swollen face, making it clear the damage went far beyond embarrassment. Powell candidly reflected,
“That just sort of really summed up my love life for the next like while.”
When asked if he managed to recover from causing such harm, he admitted there was no repairing the situation, saying,
“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.”
Though Powell’s first date disaster set a difficult tone, he later became recognized as one of Hollywood’s most eligible bachelors, often joking about how that early mishap foreshadowed his awkward romantic history.
Glen Powell’s Romantic Past and Current Relationships
Despite the chaotic beginning, Glen Powell’s love life eventually gained traction with high-profile relationships, including dating actress Nina Dobrev, television personality Renee Bargh, and model Gigi Paris. Powell and Paris ended their relationship in April 2023 after three years, according to a source who described their bond as “on the rocks” due to Powell’s demanding work schedule.

The actor was also linked romantically to Sydney Sweeney, his co-star in Anyone But You, although this occurred during Powell’s relationship with Paris. Following his split with Paris, Powell admitted that the breakup coinciding with the promotional tour for Anyone But You made the experience emotionally challenging. He stated,
“The only reason it made things harder for me to lean into that stuff was that I was going through a very real breakup amidst a promotional tour,”
acknowledging the difficulties that came with juggling personal upheaval and professional obligations.
Recently, new speculation has risen about Powell’s dating life after he was spotted with influencer Olivia Jade Giannulli, daughter of actress Lori Loughlin. On August 31, the two were seen dining at Il Cantinori in New York City with Loughlin also present. Later, Powell and Giannulli were photographed at Treasure Club, reportedly leaving together in the early hours of the morning. These sightings have stoked rumors of a potential romance.
Impact of Past Challenges on Glen Powell’s Public and Private Life
Glen Powell’s early dating disaster, marked by pain and embarrassment, contrasts sharply with his current status as a sought-after Hollywood actor. This incident reveals the awkward, sometimes painful moments before he rose to fame and established himself within the industry. His candid sharing of this story offers insight into the vulnerabilities behind his confident public image, showing his perseverance through personal challenges.
As Powell continues to navigate relationships in the spotlight, his history suggests a complicated but evolving love life. The ongoing public interest in his connections, especially with figures like Olivia Jade Giannulli, indicates that his romantic life remains a topic of attention. How these developments will influence his career and personal growth remains to be seen, but the Glen Powell first date accident remains a stark reminder of his rocky start.
