65-Year-Old Sean Penn , in Red-Hot Romance with Valeria Nicov – Age Gap Drama Goes Viral!
Sean Penn Girlfriend 2026: Hollywood icon Sean Penn is once again making headlines, but this time it’s not for his Oscar-winning performances or activist work. The 65-year-old actor has been spotted hand-in-hand with his girlfriend, 30-year-old Moldovan actress and model Valeria Nicov, and their 34-year age gap has everyone talking. From their romantic beginnings in Madrid to their recent Santa Monica shopping date, here’s everything you need to know about Sean Penn’s girlfriend and their relationship.
Who Is Sean Penn’s Girlfriend Valeria Nicov?
Valeria Nicov is a 30-year-old actress and model from Moldova who has been building her career in European entertainment since 2018. Born in 1996 in Chișinău, Moldova’s vibrant capital, Nicov has established herself as a rising talent in both the fashion and film industries.
Valeria Nicov’s Background and Early Life
Growing up in Chișinău, Nicov was immersed in a cultured atmosphere that sparked her passion for the performing arts. From an early age, she participated in school plays and explored music and dance, developing the artistic foundation that would shape her future career.
After receiving her early education in Moldova, Nicov made a pivotal move to pursue her dreams internationally. She relocated to France, where she enrolled at the prestigious Cours Florent in Paris, one of Europe’s most acclaimed dramatic arts schools. This transition marked a crucial turning point in her personal and professional development.
Her Impressive Education and Training
Nicov’s formal training is extensive and impressive. She studied at multiple renowned institutions including the Academy of Music, Theatre and Fine Arts in Chișinău, Moldova, the Actors Studio under Jack Waltzer, the Royal Academy of Dramatic Arts in London, and completed advanced studies at Cours Florent in Paris.
This comprehensive education equipped her with both classical training and contemporary techniques, preparing her for success in the competitive world of international entertainment.
A Multilingual Talent
One of Nicov’s most remarkable assets is her linguistic ability. She is fluent in multiple languages including French, English, Spanish, Russian, Romanian, and Italian. This exceptional skill set has proven invaluable in her modeling and acting career, allowing her to work seamlessly across different European markets and connect with diverse audiences.
Her Modeling Career
Nicov is represented by Premium Models, a prestigious French modeling agency based in Paris. Throughout her career, she has collaborated with several high-fashion brands and designers including Carolina Herrera, Bonanza Paris, Dada Sport, and Maison Ola.
Standing at an impressive height of almost 5’10” (177 cm), Nicov commands attention with her striking presence. Her height and poise make her an ideal figure in fashion circles, and her background in tango, yoga, and equestrian sports adds a special physical grace and control to her modeling poses.
For acting representation, she is signed to Agence Plan A in France and Engers Portelli in the United Kingdom, positioning her for opportunities on both sides of the English Channel.
Valeria Nicov’s Acting Career
While Nicov’s modeling work has brought her international recognition, she has also been steadily building her acting portfolio. Since beginning her professional acting career in 2018, she has appeared in several French productions.
Her notable credits include Paris Pigalle (2018), where she played Chloe in director Cedric Anger’s comedy, Ténor (2022), Mike, a French television series, Don’t Worry About the Kids, another French TV show, and Lineman Up: Storm Soldiers 3. She also had a small but memorable role as a bartender in the hit Netflix series Emily in Paris, which introduced her to international audiences.
In 2025, Nicov expanded her repertoire to include stage work, appearing in the play Monstre Sacré. Expressing her excitement on Instagram in February 2025, she wrote in French: “So looking forward to this! Thank you thank you thank you to the most wonderful and funny partners.”
Beyond television and film, Nicov has also appeared in short films and commercials, demonstrating her versatility as a performer.
Her Social Media Presence
Nicov maintains an active Instagram presence under the handle @valerianicov, where she has approximately 20,000 followers. Her feed strikes a balance between professional content showcasing photoshoots, runway work, and behind-the-scenes moments, and intimate glimpses into her personal life including travels, fitness routines, hobbies, and artistic poses in studio or street settings.
Her Personal Interests and Hobbies
Beyond her professional pursuits, Nicov has diverse interests that add depth to her personality. She is an avid equestrian and frequently shares her love of horseback riding with her social media followers through photos and stories.
She also has training in piano and maintains interests in boxing and other athletic activities, demonstrating her commitment to physical fitness and artistic expression.
How Did Sean Penn and Valeria Nicov Meet?
The exact circumstances of how Sean Penn and Valeria Nicov first met haven’t been publicly disclosed. However, their relationship became public knowledge in September 2024, marking the beginning of a new chapter for both.
Their Relationship Timeline
September 2024: First Public Appearance
Sean Penn and Valeria Nicov were first spotted together on September 7, 2024, in Madrid, Spain. Page Six obtained exclusive photos of the couple kissing and holding hands during a romantic date night in the Spanish capital. The images immediately sparked interest, as Penn had just months earlier expressed his contentment with being single.
October 2024: Airport Sighting
The following month, the couple was photographed together at Los Angeles International Airport, suggesting their relationship was becoming more serious as they traveled together.
November 2024: Red Carpet Debut
On November 30, 2024, Nicov and Penn made their official red carpet debut as a couple at the Marrakech International Film Festival in Morocco. The pair coordinated in elegant black ensembles as they posed for photographers, with Nicov standing by Penn’s side as he was honored with a career achievement award.
At the festival, Penn delivered an impassioned speech encouraging people to embrace diversity and political incorrectness. According to Variety, he stated: “Around the world there is this demand for diversity — but not diversity of behavior and not diversity of opinion or language. I would just encourage everybody to be as politically incorrect as their heart desires and to engage diversity and to keep telling those stories, and I’m very proud and happy to be here. Thank you.”
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May 2025: Cannes Film Festival
The couple attended the prestigious Cannes Film Festival together, where they supported the premiere of Bono’s documentary. Their appearance at one of cinema’s most celebrated events further solidified their relationship in the public eye.
July 2025: Romantic Dinner in Paris
In July 2025, Penn and Nicov were photographed enjoying a romantic dinner in Paris with some fellow famous friends, as reported by Just Jared.
October 2025: Public Forum Appearance
According to a LinkedIn post, both Nicov and Penn appeared together at a public forum, demonstrating their comfort with being seen together at professional events.
January 2026: Post-Golden Globes Outing
Most recently, on January 14, 2026, the couple was photographed enjoying a casual shopping date in Santa Monica, California, just days after Penn attended the 2026 Golden Globes ceremony.
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Their Recent Santa Monica Outing
On January 14, 2026, Sean Penn and Valeria Nicov were spotted walking hand-in-hand during a rare public outing in Santa Monica. The casual date came just three days after Penn attended the 2026 Golden Globes solo.
What They Wore
Penn kept his look casual yet polished in a white button-up shirt layered under a navy blue blazer, paired with gray or black pants and white sneakers. He was also photographed smoking a cigarette during their outing.
Nicov opted for a chic all-black ensemble consisting of a black turtleneck sweater beneath a black peacoat, black slacks or joggers, matching black sneakers, and accessorized with a black baguette bag and cat-eye sunglasses resting on her collar.
The two matched in their black and white color scheme, looking relaxed and comfortable in each other’s company as they enjoyed their shopping trip.
Sean Penn at the 2026 Golden Globes
While Nicov did not accompany Penn to the Golden Globes ceremony on January 11, 2026, the actor made headlines at the event for multiple reasons.
His Nomination
Penn was nominated for Best Performance by a Male Actor in a Supporting Role in any Motion Picture for his work in Paul Thomas Anderson’s film One Battle After Another. He was up against notable actors including Benicio del Toro, Jacob Elordi (Frankenstein), Paul Mescal (Hamnet), and Adam Sandler (Jay Kelly). The award ultimately went to Stellan Skarsgård for his role in Sentimental Value.
The Smoking Controversy
Penn went viral during the ceremony when he was spotted smoking a cigarette indoors at the grand Beverly Hilton in Los Angeles. He was photographed smoking while seated at a table with his One Battle After Another costar Leonardo DiCaprio, as well as Kate Hudson. Multiple cigarette butts were visible in a glass cup at his table, according to photos shared by The Wall Street Journal reporter Ben Fritz.
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Host Nikki Glaser’s Joke
Comedian Nikki Glaser, who hosted the ceremony, made a pointed joke about Penn’s relationship during her monologue. She quipped: “The most impressive thing is that you’ve been able to accomplish all of this [in your career] before your girlfriend turned 30. It’s just insane.”
The joke drew laughs from the audience and immediately became one of the most talked-about moments of the evening, highlighting the public’s fascination with the couple’s significant age difference.
The Age Gap: Public Reaction and Controversy
Sean Penn and Valeria Nicov’s relationship has sparked considerable discussion due to their 34 to 35-year age difference. The topic has generated mixed reactions across social media platforms.
Social Media Comments
Recent paparazzi photos of the couple shopping in Santa Monica have reignited conversations about their age gap. Some social media users have been critical, with comments ranging from surprise about the height difference to more harsh criticisms. One viral comment stated: “I thought he was her grandfather.”
However, others have defended the relationship, pointing out that both are consenting adults and appear genuinely happy together. Supporters note the genuine affection visible in their public appearances, with the couple frequently photographed holding hands, smiling, and enjoying each other’s company.
Penn’s History with Age-Gap Relationships
This is not Penn’s first relationship with a significant age difference, though it is his largest known age gap to date. His third wife, Leila George, is approximately 32 years his junior. Penn is actually the same age as George’s mother, actress Greta Scacchi, and only one year younger than her father, actor Vincent D’Onofrio.
After divorcing George in 2022, Penn briefly dated Ukrainian actress Olga Korotyayeva, who is about 20 years his junior.
Penn’s Previous Statements on Being Single
The relationship came as somewhat of a surprise given Penn’s comments in a June 2024 interview with The New York Times, where he expressed his contentment with being single. “I’m just free,” he said at the time. “If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it, and I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.”
Just three months later, he was photographed kissing Nicov in Madrid, suggesting his perspective on relationships had evolved.
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Valeria Nicov’s Celebrity Friendships
One of Nicov’s closest friendships is with French actress Camille Razat, who plays Camille in the Netflix series Emily in Paris. The two women connected while filming the French film Paris Pigalle and have remained close ever since.
Razat frequently appears on Nicov’s Instagram feed, and the pair has been photographed spending quality time together on multiple occasions. In August 2023, Nicov shared photos of herself and Razat enjoying time outdoors, captioning the post: “You burst inside my heart.”
This friendship has given Nicov connections within the international entertainment community and demonstrates her ability to maintain meaningful relationships in the industry.
Sean Penn’s Dating History: A Look Back
To understand Sean Penn’s current relationship with Valeria Nicov, it’s helpful to examine his extensive romantic history, which includes three marriages and relationships with some of Hollywood’s most famous women.
Marriage #1: Madonna (1985-1989)
Sean Penn’s first marriage was to pop superstar Madonna, who is actually two years older than him. The two met on the set of Madonna’s “Material Girl” music video in January 1985, and their romance was instant and intense.
They married on August 16, 1985—Madonna’s 27th birthday—in a white wedding ceremony in Malibu. Penn turned 25 the next day. Their relationship was highly publicized and tumultuous, marked by intense passion and Penn’s well-documented conflicts with the paparazzi.
The couple attempted to collaborate professionally, starring together in the 1986 film Shanghai Surprise, which proved to be both a critical and commercial failure. Madonna dedicated her third studio album True Blue (1986) to Penn, referring to him in the liner notes as “the coolest guy in the universe.”
However, their marriage was troubled. An unauthorized 1991 biography alleged that Penn had been physically abusive during their marriage. Both Penn and Madonna have vehemently denied these allegations. In 2015, when Penn filed a defamation lawsuit against director Lee Daniels over similar claims, Madonna provided a statement declaring: “I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me. These allegations are completely outrageous, malicious, reckless, and false.”
Madonna filed for divorce in December 1987 but withdrew the papers two weeks later. She filed again in January 1989, and the divorce was finalized that year. Despite their difficult split, the former couple has since developed a friendship. Madonna revealed in the 1991 documentary In Bed With Madonna that Sean was the love of her life. Penn showed his support by attending two shows of her 2015 Rebel Heart tour, and the pair happily posed together on the red carpet at the 2016 “Help Haiti Home” gala benefit.
Brief Romance: Elizabeth McGovern (Mid-1980s)
Before marrying Madonna, Penn dated actress Elizabeth McGovern, his co-star in the 1984 film Racing with the Moon. The two were even engaged at one point. McGovern, who is just one year younger than Penn, later recalled in a 2010 interview with the Daily Mail that their relationship was “so exhausting.”
“I didn’t want to get married, but he did—or at least he said he did,” she told the publication. “I couldn’t sustain it. We also wanted to do different things. He likes to pretend he’s not really a Hollywood person, but he is.”
Brief Relationship: Jewel (1995)
During a separation from Robin Wright in 1995, Penn briefly dated singer-songwriter Jewel. He reportedly reached out to her after seeing her perform on Late Night with Conan O’Brien, inviting her to compose a song for his film The Crossing Guard.
In her memoir Never Broken: Songs Are Only Half the Story, Jewel recounted: “One day, my dad came to find me, saying, ‘Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn.'”
Marriage #2: Robin Wright (1996-2010)
Penn’s longest and perhaps most significant relationship was with actress Robin Wright, best known for her roles in The Princess Bride, Forrest Gump, and House of Cards. The two began dating in 1989, shortly after Penn’s divorce from Madonna.
Their daughter, Dylan Frances Penn, was born on April 13, 1991, followed by their son, Hopper Jack Penn, on August 6, 1993. The couple married on April 27, 1996, after seven years together and having two children.
Their marriage was characterized by numerous separations and reconciliations. They filed for divorce in December 2007 but reconciled several months later, requesting a court dismissal of their divorce case. In February 2009, Robin accompanied Penn to the Oscars, where he won Best Actor for his role in Milk. Just two months later, he filed for legal separation but withdrew the petition in May 2009.
Robin filed for divorce for the final time in August 2009, with no desire to reconcile. Their divorce was finalized in July 2010.
Wright later told The Telegraph about their tumultuous relationship: “Divorce in and of itself, and with children, is devastating. Worse than that. One of the reasons why we got back together and broke up so much was trying to keep the family together. If you’ve got kids, it’s a family, and you try again, and you try again. We did that for a long time.”
Penn has since stated that while he and Wright don’t always get along perfectly, they have managed to co-parent their now-adult children effectively.
Other Notable Relationships
After his divorce from Wright, Penn was briefly linked to actress Scarlett Johansson in 2011. While the relationship was never officially confirmed, the two were spotted together on multiple occasions, most notably at the White House Correspondents’ Dinner in May 2011.
Penn’s most high-profile post-Wright relationship was with Academy Award-winning actress Charlize Theron. The two began dating in late 2013 and got engaged in 2014. However, their engagement was called off in 2015, leading to the end of their relationship. Neither has explicitly stated the reasons for their breakup.
Marriage #3: Leila George (2020-2022)
Penn’s third and most recent marriage was to Australian actress Leila George, the daughter of actors Vincent D’Onofrio and Greta Scacchi. The couple began dating in 2016 and married on July 30, 2020, during a quiet home ceremony amid the COVID-19 pandemic.
During an August 2020 appearance on Late Night With Seth Meyers, Penn explained: “Yeah, we did a Covid wedding. By that, I mean it was a county commissioner on Zoom and we were at the house, my two children and her brother, and we did it that way.”
The marriage was short-lived. George filed for divorce in October 2021, just over a year after they tied the knot. Their divorce was finalized on April 22, 2022.
Penn later took full responsibility for the failed marriage, admitting in an interview with Hollywood Authentic: “There’s a woman who I’m so in love with, Leila George, who I only see on a day-to-day basis now, because I f—ed up the marriage. We were married technically for one year, but for five years, I was a very neglectful guy.”
He continued: “I was not a f—ing cheat or any of that obvious s–t, but I allowed myself to think that my place in so many other things was so important, and that included my place in being totally depressed and driven to alcohol and Ambien at 11 o’clock in the morning, by watching the news, by watching the Trump era, by watching it and just despairing.”
Brief Relationship: Olga Korotyayeva (2023)
Following his divorce from George, Penn briefly dated Ukrainian actress Olga Korotyayeva starting in June 2023. The two were spotted vacationing in Rome and were last seen together in October 2023 on a dog walk. Korotyayeva, who has starred in several films since 2010, is approximately 20 years Penn’s junior. The relationship appears to have ended before Penn began seeing Nicov in 2024.
Brief Relationship: Nathalie Kelley (Late 2023)
In December 2023, Penn was photographed with Peruvian-Australian actress Nathalie Kelley, best known for her role in The Vampire Diaries. The two looked happy together as they walked through Miami Beach, though the status of their relationship was never confirmed. The two likely bonded over their shared interests in activism and humanitarian efforts, as Kelley sits on the board of foundations like Kiss the Ground and the Fungi Foundation.
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Penn’s Children: Dylan and Hopper
From his marriage to Robin Wright, Penn has two adult children who have both pursued careers in entertainment.
Dylan Frances Penn
Born April 13, 1991, Dylan is an actress and model who has appeared in films and graced the covers of major fashion magazines. She has inherited both her parents’ striking looks and artistic talents.
Hopper Jack Penn
Born August 6, 1993, Hopper has followed in his father’s footsteps as an actor and has appeared in several films. Both children maintain relationships with both of their parents despite their parents’ difficult divorce.
What Makes Their Relationship Work?
Despite the significant age difference and public scrutiny, several factors suggest that Penn and Nicov have found genuine connection.
Shared Interests
Both Penn and Nicov are deeply involved in the arts—Penn as an acclaimed actor and director, and Nicov as an actress and model. This shared passion for creativity and performance likely provides common ground for their relationship.
Mutual Respect for Independence
Penn has consistently emphasized his need for freedom and independence in relationships. Nicov, as an ambitious professional building her own career, appears to respect this need while maintaining her own identity and pursuits.
Low-Key Approach
The couple has largely kept their relationship out of the spotlight, making only occasional public appearances at major events. This privacy-focused approach may help protect their relationship from excessive media pressure.
Genuine Affection
In their public appearances, the couple displays obvious affection and comfort with each other. The photos of them holding hands, smiling, and enjoying simple activities like shopping suggest a relationship built on genuine connection rather than publicity.
Penn’s Current Career and Life
At 65, Sean Penn remains one of Hollywood’s most respected actors. His recent work includes:
One Battle After Another
Penn’s role in Paul Thomas Anderson’s One Battle After Another earned him a Golden Globe nomination for Best Supporting Actor in 2026. The film won five awards total at the ceremony, including Best Motion Picture – Musical or Comedy, demonstrating Penn’s continued relevance in cinema’s upper echelons.
Humanitarian and Activist Work
Penn has long been known for his humanitarian efforts and political activism. He has been involved in disaster relief efforts, including founding the nonprofit organization Community Organized Relief Effort (CORE), which provided aid following the 2010 Haiti earthquake and has since expanded to other disaster and crisis responses.
Future Projects
Penn continues to be actively involved in both acting and directing, with several projects in various stages of development.
What’s Next for Sean Penn and Valeria Nicov?
As of January 2026, Sean Penn and Valeria Nicov appear to be going strong. Their relationship, which has now lasted over a year since their first public appearance, suggests more than just a passing romance.
Will They Make More Public Appearances?
Given their preference for privacy, it’s unclear how often the couple will step out publicly together. However, with Penn’s continued presence at awards season events and film festivals, there may be more opportunities to see them together on red carpets.
Career Impact for Nicov
Dating one of Hollywood’s most famous actors has undoubtedly raised Nicov’s profile internationally. Whether she chooses to leverage this attention to further her career remains to be seen, but her established work in European entertainment suggests she has her own path independent of her famous boyfriend.
Long-Term Prospects
Penn has been married three times and has stated he doesn’t expect to have his heart broken by romance again. Whether his relationship with Nicov will lead to a fourth marriage or remain a significant partnership outside of marriage is something only time will tell.
Lessons from Their Relationship
The relationship between Sean Penn and Valeria Nicov offers several interesting observations about modern romance:
Age Is Just a Number?
While their 34-year age gap raises eyebrows, both are consenting adults who appear genuinely happy together. Their relationship challenges conventional ideas about appropriate age differences in romantic partnerships.
Privacy in the Public Eye
Despite both being in the entertainment industry, the couple has managed to maintain a relatively private relationship, making strategic public appearances while keeping the intimate details of their romance out of the tabloids.
Second (and Third, and Fourth) Chances at Love
Penn’s willingness to open himself to romance again after three divorces demonstrates resilience and hope. His relationship with Nicov suggests that finding connection is possible at any age and after any number of heartbreaks.
International Love
The relationship between an American actor and a Moldovan model-actress highlights how global the entertainment industry has become, with artists from different countries finding common ground across cultural boundaries.
Conclusion
Sean Penn’s relationship with Valeria Nicov marks a new chapter in his long romantic history. Despite a 34-year age gap and public scrutiny, the couple appears genuinely happy.
Nicov is an accomplished model and rising actress with strong education and multilingual skills, building her own career beyond Penn’s fame. After three failed marriages, Penn’s decision to love again has drawn attention. For now, they seem content together, letting time decide their future.
