The glitz and glamour of awards season often give way to the quiet, everyday moments that define Hollywood’s most private couples. Just days after the 83rd Annual Golden Globe Awards captivated audiences worldwide, legendary actor Sean Penn opted for a change of pace, swapping his red-carpet tuxedo for casual attire during a serene afternoon in Santa Monica. On January 14, the 65-year-old Oscar winner was spotted enjoying a low-key date with his girlfriend, 30-year-old model Valeria Nicov. The pair, who have largely kept their romance out of the relentless glare of the paparazzi, appeared relaxed and deeply in sync as they strolled hand-in-hand through the coastal city.
For their Monday excursion, the couple leaned into a comfortable, understated aesthetic. Penn looked every bit the casual California local, sporting a classic navy blue jacket layered over a crisp, white long-sleeved button-down shirt. He paired the look with charcoal gray trousers and clean white sneakers, a practical choice for a daytime walk. Nicov, who stands as a striking presence beside the veteran actor, opted for a monochromatic, all-black ensemble. Her outfit featured a structured peacoat worn over relaxed joggers, finished with athletic tennis shoes—a perfect blend of high-fashion sensibility and off-duty comfort.
This public appearance is a notable rarity for the duo. While Penn has been a fixture of the Hollywood landscape for decades, he and Nicov have been selective about their joint outings. Their relationship first garnered significant international attention in November 2024, when they made their official red-carpet debut at the Marrakech International Film Festival. Since then, they have managed to navigate their relationship with a level of discretion that is increasingly rare in the age of social media. Notably, Nicov was not present by Penn’s side during the Golden Globes ceremony earlier in the week, where the actor was a central figure in one of the night’s most prestigious categories.
Penn entered the 2026 Golden Globes as a nominee for Best Performance by a Male Actor in a Supporting Role in any Motion Picture for his compelling work in the critically acclaimed drama One Battle After Another. Although the trophy ultimately went to veteran actor Stellan Skarsgård, Penn’s presence at the ceremony was anything but somber. Having finalized his divorce from actress Leila George in 2022 after a two-year marriage, Penn appeared to be in high spirits throughout the evening, embracing the celebratory atmosphere of the Beverly Hilton.
Perhaps the most talked-about moment involving Penn during the telecast was his reaction to the sharp-witted monologue delivered by host Nikki Glaser. Known for her fearless brand of "roast" comedy, Glaser did not hold back when she turned her sights on the Milk star. "Everyone in this town is obsessed with looking younger, but Sean Penn is like, ‘What if I slowly morph into a sexy leather handbag?’" Glaser quipped from the stage. The joke, which poked fun at Penn’s famously rugged and weathered appearance, landed perfectly. Rather than taking offense, Penn was seen on camera laughing heartily and nodding in agreement, clearly appreciating the comedian’s perspective. "It’s hot. It’s good," Glaser added, acknowledging Penn’s good-natured response.
Glaser’s routine also touched upon Penn’s well-known reputation as a devoted humanitarian. Over the years, Penn has frequently put himself in the crosshairs of global conflicts and natural disasters to provide aid and bring attention to various crises. However, Glaser found a way to inject her signature edge into this aspect of his life as well. "I feel like a lot of actors talk the talk, but Sean Penn will actually go to the places in the world that need help the most and he will do cocaine there," she joked. The room erupted in laughter, and Penn himself continued to chuckle as Glaser doubled down on the punchline: "Sean, I did get permission to do that joke from your two best friends Charlie Sheen and El Chapo."
The comedy didn’t end when the cameras stopped rolling. In a post-show interview on The Howard Stern Show on January 13, Glaser revealed that her "joke bucket" for Penn was actually much deeper than what made it into the live broadcast. She shared several zingers that were left on the cutting room floor, including a line about Penn’s physical intensity. "Sean Penn is nominated tonight, I’m assuming for Best Neck Veins," she read from her notes. Another unused gem described the actor as looking like "the defiant last tree standing in a rainforest." These revelations provided a glimpse into the rigorous process of awards show hosting, where even the funniest material must be trimmed for time and tone.
While Penn and Nicov’s Santa Monica walk provided a glimpse into the actor’s private life, the Golden Globes themselves were a treasure trove of unscripted moments and star-studded interactions that fans didn’t see on the televised broadcast. Behind the scenes, the "inner circle" of Hollywood was in full effect. Leonardo DiCaprio was spotted sharing a warm moment with Owen Cooper, the breakout star of the hit series Adolescence. Cooper, who took home the award for Best Supporting Male Actor in a TV Series, has become the "it-boy" of the season, with even the industry’s biggest titans eager to offer their congratulations.
The night was also a major milestone for Teyana Taylor, who delivered a powerhouse performance in One Battle After Another. In a surprise win that left her visibly emotional, Taylor secured the Golden Globe for Best Supporting Actress in a Motion Picture, beating out stiff competition that included Wicked: For Good star Ariana Grande. Despite the competitive nature of the category, Taylor was seen radiating joy backstage, proving that 2026 is truly her year to shine.
Meanwhile, the "power couple" energy was high as Kylie Jenner and Timothée Chalamet attended their third consecutive Golden Globes together. The night was particularly special for Chalamet, as it marked his first win in Jenner’s presence. He took home the trophy for Best Lead Actor in a Motion Picture, Comedy or Musical, for his transformative role in Marty Supreme. The couple appeared as smitten as ever, often leaning in for private whispers amidst the chaos of the ballroom.
Longtime friends and Hollywood royalty Julia Roberts and George Clooney also reminded everyone why they remain the gold standard of industry camaraderie. Though both are happily married to their respective partners, their chemistry as "figureheads" of the industry remains unmatched. Roberts received a resounding standing ovation when she took the stage to present the final award of the night—Best Motion Picture, Musical or Comedy—to the cast and crew of One Battle After Another. Later, she was seen in a deep, animated conversation with Leonardo DiCaprio, the two of them looking every bit the part of Hollywood’s most elite inner circle.
The evening was also a family affair for some. Selena Gomez was joined by her husband, Benny Blanco, at a table that felt more like a gathering of best friends than a professional event. Seated with her Only Murders in the Building costars Steve Martin and Martin Short, the group shared a "Kodak moment" captured by Martin himself. Nearby, Jennifer Lawrence was seen stopping by the table to say hello to Kylie Jenner, proving that even A-listers aren’t immune to a bit of fan-girling when it comes to the Kardashian-Jenner clan.
Other notable sightings included a White Lotus reunion between Patrick Schwarzenegger and Parker Posey, and a sweet moment between Justin Hartley and Sterling K. Brown. Hartley appeared to be checking in on his former This Is Us costar, who had been seen nursing a leg injury during the previous awards cycle. Additionally, Noah Wyle, fresh off a win for Best Actor in a Drama Series for his work in The Pitt, was overheard joking about his long history of playing medical professionals. Wyle, who famously rose to fame on ER, playfully suggested that his recent trophy haul might finally prove he’s a "better doctor" than his former costar George Clooney.
As the 2026 awards season continues to unfold, the contrast between the high-octane energy of the Golden Globes and the quiet intimacy of a Santa Monica stroll serves as a reminder of the dual lives these icons lead. For Sean Penn, a man whose career has been defined by intensity and transformation, finding a balance between the "sexy leather handbag" jokes of the ballroom and the hand-holding walks with Valeria Nicov seems to be his most successful role yet. While the trophies may go to different hands each year, the enduring fascination with Hollywood’s elite—and the private moments they share when the cameras are away—remains the industry’s most compelling narrative.
