Regarding his present romantic relationships,Sean Pennnot receiving approval from everyone.
The actor’s romantic past sounds like a celebrity guest list — Robin Wright, Scarlett Johansson, Charlize Theron, and even Madonna.
Nevertheless, over the past year, he has been associated with a Moldovan actress and model, and fans are continually noticing a significant contrast between them that makes their relationship seem less stylish and more uncomfortable.
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On Wednesday, January 14, Penn was seen walking through Santa Monica with his significantly younger girlfriend, Valeria Nicov, holding hands. His gray hair and the lines on his face spoke volumes next to Nicov’s smooth skin and dark hair — a comparison that silently highlighted the age difference without anyone needing to calculate it.
At 65, the actor from “Fast Times at Ridgemont High” is more than three decades older than Nicov.
The age difference didn’t appear to bother either of them. Nicov, fully dressed in black, smiled during the walk, while Penn kept it relaxed in a navy blazer and white dress shirt, holding a cigarette. The 30-year-old seemed to stand taller than the “Mystic River” actor, making the walk a visual reminder that time—and height—aren’t on the same side.
Even if the couple appears unaffected by the age difference, fans have not been nearly as understanding.
One reader from the Daily Mail who found it to be unappealingwrote,What do a 65-year-old man and a 30-year-old have in common? My goodness, just grow up already.
Over the course of his 14-year relationship with Robin Wright, Penn became a father to two children: daughter Dylan Frances Penn, who is 34, and son Hopper Jack Penn, aged 32.
Another individual who is not fond of this pairingnotedHis girlfriend is younger than his daughter… I find that somewhat unsettling.
Another individual expressing their opinions on the mattertypedNever understand why these young women are drawn to an old man, I’m old and I don’t even like them! Money must be a big factor, close your eyes, and you won’t notice the wrinkles and the tired body. Ugh.
Another observed, “The ‘woman’ physically looms over him like an NBA player.”
This is not the first time Penn has faced a significant age difference. Throughout the years, he has been in relationships with several women much younger than him, such as singer Jewel in the 1990s, who is 14 years younger. He then dated Scarlett Johansson in 2011, with an age gap of approximately 24 years, and later Charlize Theron in 2013, who is 15 years younger. The age difference became even more pronounced with his third ex-wife, Leila George, who is 32 years younger. After their breakup, he started dating Olga Korotyayeva, who is about 20 years younger.
As for Nicov, it remains unknown when or how they met, but Penn has been associated with her since late September 2024. The couple was first seen sharing a passionate kiss in Madrid, with Nicov initiating the moment. The next month, they were spotted together again at Los Angeles International Airport, dressed in casual attire, indicating their relationship remained strong.
In November 2024, Penn and Nicov made their red carpet appearance at the 21st Marrakech International Film Festival in Morocco, where Penn was honored with a career achievement award.
One of the most recent instances when the duo was spotted together occurred at the 78th annual Cannes Film Festival in May 2025.
‘The Woman Seems to Overwhelm Him’: Images of Actor Sean Penn and His 30-Year-Old Partner Have Followers Observing More Than Just Their Age Difference