Fresh romance speculation has emerged in Hollywood circles after actor Stephen Dorff was spotted enjoying a late-night outing in Los Angeles with musician Amanda Shires, the former wife of acclaimed country artist Jason Isbell. The pair were photographed walking hand-in-hand as they arrived at the legendary Chateau Marmont, a venue long associated with celebrity intrigue and high-profile encounters.
A Late-Night Sighting at a Storied Venue
The sighting occurred at one of Hollywood's most iconic and historically significant celebrity hotspots, where the duo appeared comfortable in each other's company. Dorff, aged 52, maintained a casual yet rugged aesthetic for the evening, opting for a worn brown leather jacket layered over a simple white T-shirt and an open blue button-down shirt. He completed his ensemble with light-wash jeans, black and green sneakers, and a baseball cap, walking closely beside his companion throughout their arrival.
Shires, who is 43 years old, presented an effortlessly chic appearance in an all-black outfit that included a leather jacket, cropped trousers, and pointed heels. She carried a structured black handbag and wore her dark hair loose, occasionally glancing downward as the pair navigated the sidewalk together. Neither individual has offered any public comment regarding the precise nature of their relationship, leaving observers to speculate based on their visibly close interaction.
Background of Amanda Shires' Previous Marriage
This development arrives approximately two years after Shires' highly publicised separation from country music star Jason Isbell, a split that sent considerable shockwaves through the Americana and country music communities. In February 2024, Isbell, aged 46, formally filed for divorce from Shires following nearly eleven years of marriage, citing irreconcilable differences in the legal paperwork submitted in Tennessee.
Despite initially separating in December 2023, the couple only finalised their divorce proceedings in March 2025. Throughout their marriage, Isbell and Shires frequently collaborated on professional projects, with Shires providing backup vocals for Isbell's band while Isbell contributed guitar work for Shires' band, The Highwomen. The former couple share one daughter, Mercy, who is nine years old.
Public Reflections on Marital Challenges
Both artists have spoken openly in previous years about the difficulties they encountered within their relationship, particularly during the challenging period of the COVID-19 pandemic. In a 2022 interview with People magazine, Shires reflected philosophically, stating, "It doesn't matter if you're a quasi-famous person like Jason or me, everybody's relationships are the same; there's ups and downs and there's good and bad and you just try to deal with it. Life's not easy, marriage isn't easy, but aren't we lucky to be able to live."
Isbell previously addressed this turbulent phase in a 2020 discussion with The New York Times, acknowledging that his intensive work on the album Reunions led to emotional withdrawal. He remarked at the time, "At one point, I said, 'It'd be easier if somebody had cheated.' But it was more like, 'We don't know each other right now. We're not able to speak the same language.'" During this strained period, Shires temporarily relocated to a hotel to create necessary space, later channelling the emotional turmoil into her music, including the song Fault Lines which references the couple's experienced disconnect.
Despite reconciling after that particularly low point and endeavouring to sustain their marriage over the subsequent three years, the pair ultimately concluded that parting ways was the most appropriate decision. The recent sighting of Shires with Stephen Dorff now introduces a new chapter of speculation regarding her personal life following the conclusion of her high-profile marriage to Jason Isbell.
