
Sean Penn Spotted Packing on the PDA with Actress 34 Years His Junior
Sean Penn is sparking fresh romance rumors after being caught in a series of intimate moments with actress Valeria Nicov on the streets of Madrid over the weekend. Since his divorce from Leila George, the 64-year-old titan has been frequently spotted in the company of a string of young, glamorous women.
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According to Daily Mail, Penn and Nicov were photographed looking very much like a couple during a weekend date in the Spanish capital. The 64-year-old Oscar winner and his younger flame opted for casual attire and appeared unable to take their eyes off one another. The pair was seen laughing, sharing affectionate gestures, and locking lips in a passionate street-side “make-out” session.
Penn’s new interest is 30-year-old Valeria Nicov, a Moldovan model and actress. A polyglot who speaks several languages, Nicov has appeared in a handful of indie projects since 2018. The age gap between the Mystic River star and Nicov is a notable 34 years—making her younger than both of the actor’s adult children.
Since finalizing his divorce from actress Leila George (who was 32 years his junior) in 2022, Penn has fully embraced the bachelor lifestyle. Before his outing with Nicov, the ex-husband of Madonna had been linked to Olga Korotyayeva, Nathalie Kelley, and several other beauties.
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Just months ago, Penn opened up about his newfound happiness in flying solo. Speaking to The New York Times in June 2024, the Hollywood veteran expressed a desire for casual dating while avoiding emotional turmoil. “I’m just free. If I’m going to be in a relationship, I’m still going to be free,” the Academy Award winner stated. “I don’t think I’m going to have my heart broken by romance again.” He also noted that while he used to crave drama in his love life, he now feels differently; even when “madly in love,” unnecessary conflict is a total dealbreaker for him.
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Penn further reflected on his past, admitting that throughout his life, his relationships often fell into a pattern where “the first thing I notice in the morning is wondering what I’m going to do to make them happy that day.” The actor added poignantly that this level of devotion was “rarely reciprocated.”
Born in 1960, Sean Penn is a powerhouse actor and director in Hollywood. After making his debut with a minor role in Little House on the Prairie (1974), he rose to stardom in classics like Fast Times at Ridgemont High, Bad Boys, and At Close Range. His powerhouse performances in Dead Man Walking and I Am Sam solidified his status, while his directorial efforts earned critical acclaim. Over a career spanning more than 50 films, he has secured two Best Actor Oscars for his roles in Mystic River (2003) and Milk (2008).
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Beyond his talent, Penn is notorious for his complex and high-profile dating history. He has been linked to a roster of A-listers including Elizabeth McGovern, Jewel, Charlize Theron, and Scarlett Johansson. He has walked down the aisle three times: first to Madonna in 1985 (a marriage that dominated tabloids before ending four years later), followed by a tumultuous, on-and-off marriage to Robin Wright. The pair, who share two children, wed in 1996 and finalized their divorce in 2010. Most recently, he married Leila George in 2020, though the union collapsed after just over a year.
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Sean Penn Rediscovered His Love of Acting With One Battle After Another
In Paul Thomas Anderson’s political thriller One Battle After Another, Sean Penn steps fully into villain mode. He plays Colonel Steven J. Lockjaw, a hardline military zealot whose authority is threatened when an immigration detention center he oversees is targeted by a group of left-wing revolutionaries, including Perfidia Beverly Hills (Teyana Taylor) and her partner, Pat Calhoun (Leonardo DiCaprio). A secret connection between Lockjaw and Perfidia reverberates throughout the film, setting the story on a collision course 16 years later. At the center of it all is Perfidia’s daughter, played by Chase Infiniti, whose existence draws Lockjaw back into a past he thought had been handled.
While One Battle After Another is only Penn and Anderson’s second movie together—following 2021’s Licorice Pizza—their friendship goes back decades. As Penn readily admits, working with Anderson helped shake off a long stretch of disillusionment with acting. His performance is electrifying—full of menace, rage, and humor—earning him a Golden Globe nod for best supporting actor, among the film’s nine total nods.

How did you meet Paul Thomas Anderson?
We’ve known each other for a very long time. My older brother scored his first two movies. Around 1990, my brother called and said he had a friend, a young director who had made a film, and would I give him some advice? When I look back on that today, it would be as if my brother asked me to call John Huston, one of the greatest directors of all time, to give him some advice.
We came close to working together before Licorice Pizza, which I was in. Paul offered me Punch-Drunk Love, the movie with Adam Sandler, but not the Adam Sandler part.
You were great in Licorice Pizza as Jack, who was based on the actor William Holden.
I thought I looked a bit bloated, but thank you. It was a charming movie. Bradley Cooper makes me giggle in that film. And I started hearing that Paul was going to send me another script. When he finally sent it to me, I was traveling and I took it with me. Late at night, still dripping wet from a shower, I grabbed it just to taste the opening pages. I sat there naked, laughing and really excited because Paul is always in totally different worlds. I thought to myself, Okay, he’s going there!
You play a military man in One Battle After Another. Did you do any special preparation?
Because of other aspects of my life, I’ve spent a lot of time around that culture. As for any preparation, this one felt like, “Shut up, Sean. Stay out of their way.”

Are you more like a cat or a dog?
Dog. But I do have a certain aloofness. I think Bob Dylan is credited with saying, “I’m not elusive, man. I’m exclusive.” I don’t get along with people in groups too much. I like small numbers of people to contend with. And, like a dog, I can be distracted by a bone that’s thrown. I am trying to train myself.
For a while, you seemed disillusioned with acting. That seems to have changed recently.
Eighteen years ago, when I did Milk, was the last time that I enjoyed the work. But you want to be participating in something that is of your current interest, and with people who are surprising. Because of Paul’s movie, I’m in a stage of liking acting. But I’ve always got carpentry to fall back on. And surfing.

Do you think there’s a connection between surfing and acting?
There was a surfer named Ben Aipa who said it was not about overpowering a wave but matching its power and finding that flow zone. That first read of Paul’s script was like sensing the wave and looking for a takeoff point. With a director like Paul, you’re getting great guidance to that takeoff point. Then you just flow.
You’re a longtime smoker. When did you start?
I must have been 22. I saw myself as an un-addictable person. W. Somerset Maugham has a quote: “Men are vain, particularly young men.” I was making a World War II–era movie called Racing with the Moon, and we were smoking unfiltered Ovals the whole time. After the shoot finished, this dark green carton of Turkish Ovals in the tobacconist’s store started calling me, saying, “You’re forgetting something.” I got a carton, and I’ve been smoking ever since. I don’t try to quit anymore. I love it. I don’t recommend it for anybody, but I love it. Now I smoke American Spirit yellow.
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What’s your drink of choice?
Vodka tonic only, even at a wedding. I say, “I will drink with you, but I’m not going to be bullied or peer pressured. I only drink vodka tonic.”
Do you have actors you’ve looked up to?
I have a real affection for smart people who do work with a real commitment. When I was in acting school, Robert De Niro’s particular focus and concentration appealed to me a lot. I revered him and still do. He became a friend, a mentor, and a big brother.
Are you a superstitious person?
I think I’ve lived long enough to assume that something like karma exists. I have a little protocol that I go through: I have an anthropomorphic relationship with planes, and I make promises, so the plane will make me promises. And then I remember that [former Egyptian president] Anwar Sadat said, “I’m going to die, but not one second before God says so.” And then I remember that I’m in the air already. There’s nothing to do.
Style Director: Allia Alliata di Montereale. Codirector: Frank Lebon. Director of photography: André Chemetoff. Hair by Jawara for L’Oréal Professional at Art Partner; makeup by Lauren Parsons for Sisley Paris at Art Partner; manicure by Jolene Brodeur for Dazzle Dry at the Wall Group. Set design by David White at Streeters.





























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