Dean Winters Confirms Relationship With Actor Glori Dei Filippone
The 62-year-old actor and 28-year-old model recently debuted their relationship on social media.
1Public Relationship Confirmation
Actor Dean Winters, aged 62, has officially confirmed his romantic relationship with 28-year-old model and actor Glori Dei Filippone. The couple recently appeared together at a special screening of the film Ebenezer in New York. Filippone, who identifies as nonbinary, shared photos of the pair on Instagram on November 8.
2Social Media Interaction
Following the Instagram post captioned 'Til the wheels fall off,' the couple received significant attention from followers. When a commenter labeled the post a 'hard launch,' Winters responded by stating there was 'nothing soft' about their announcement. He also expressed enthusiasm for introducing his partner to friends in future social gatherings.
3Winters' Career Background
Dean Winters is widely recognized for his portrayal of Ryan O'Reily in the HBO series Oz. Beyond his dramatic work, he gained significant cultural visibility as the character Mayhem in a long-running series of Allstate Insurance commercials. His extensive television resume also includes notable appearances on 30 Rock and Brooklyn Nine-Nine.
4SVU Tenure and Departure
Winters originally appeared as Detective Brian Cassidy during the inaugural season of Law & Order: Special Victims Unit. He left the series following the first season due to a contractual obligation with HBO. He later revealed in a 2015 interview that this departure stemmed from a specific dispute regarding his existing network commitments.
5Unexpected Series Return
The actor returned to the SVU set over a decade later after a chance encounter with the production crew outside his apartment. After a brief interaction with Mariska Hargitay, he was invited back to the show. He subsequently appeared as a recurring character throughout the show's 14th and 15th seasons.
6Character Narrative Arc
During his return to the procedural drama, Winters' character, Brian Cassidy, engaged in a romantic storyline with lead character Olivia Benson. This narrative arc provided a significant shift for his character, who had previously transitioned from the SVU team to Narcotics. The relationship between Brian and Olivia eventually concluded on screen.
7Recent Professional Activity
While Winters has maintained a consistent presence in television, his involvement with Law & Order: SVU has been sporadic since his initial departure. Outside of his recurring role in the mid-2010s, he has not been a regular cast member. He made a brief return to the long-running series during the 2025 season.
8Personal Life Context
The relationship between Winters and Filippone highlights the actor's current personal life amidst his ongoing career in entertainment. At 62, Winters continues to balance high-profile commercial work with occasional television appearances. This public confirmation marks a rare moment of personal disclosure for the actor, who typically focuses on his professional projects.
Original article: Us Weekly — Dean Winters Confirms Relationship With Actor Glori Dei Filippone