When it comes to his current love life, Sean Penn isn’t getting a stamp of approval from everyone.
The actor’s dating history reads like a red carpet roll call — Robin Wright, Scarlett Johansson, Charlize Theron, even Madonna.
However, for the last year, he’s been linked to an actress and model from Moldova, and fans can’t stop side-eyeing one glaring difference between the two that makes their relationship feel less glamorous and more awkward.
On Wednesday, Jan. 14, Penn and his much-younger girlfriend, Valeria Nicov, were spotted strolling through Santa Monica hand in hand. His gray hair and well-earned wrinkles did all the talking beside Nicov’s smooth skin and dark hair — a side-by-side that quietly screamed decades apart without anyone needing to do the math.
At 65, the “Fast Times at Ridgemont High” actor is more than three decades older than Nicov.
The age gap didn’t seem to faze either of them. Nicov, dressed head-to-toe in black, smiled through the walk as Penn kept it casual in a navy blazer and white button-down, cigarette in hand. The 30-year-old even appeared to tower over the “Mystic River” actor, turning the stroll into a visual reminder that time — and height — are not playing on the same team here.
Even if the couple seems unfazed by the age gap, fans haven’t been nearly as forgiving.
One Daily Mail reader who thought it was off putting wrote, What does a 65 yr old man have in common with a 30-year-old? My gawd, grow up already.”
During his 14-year marriage to Robin Wright, Penn welcomed two children: daughter Dylan Frances Penn, 34, and son Hopper Jack Penn, 32.
A second person who doesn’t like this match up noted, “His girlfriend is younger than his daughter….I find that a bit disturbing.”
Another person sharing their thoughts about it typed, “Never know why these young women like an old man, I’m old and I don’t even like them! Money plays a big part I’m sure, close your eyes, you won’t see the wrinkles and wasted body. Ugh.”
Another noted, “The ‘woman’ literally towers over him like a NBA player.”
This isn’t Penn’s first run-in with a sizable age gap. Over the years, he’s dated several women significantly younger than himself, including singer Jewel in the 1990s, who is 14 years his junior. He later dated Scarlett Johansson in 2011 despite an age difference of about 24 years, followed by Charlize Theron in 2013, who is 15 years younger. The gap grew even wider with his third ex-wife, Leila George, who is 32 years younger than Penn. After their split, he went on to date Olga Korotyayeva, who is roughly 20 years his junior.
As for Nicov, it’s unclear when or how they met, but Penn has been linked to her since late Sept. 2024. The two were first spotted sharing a steamy kiss in Madrid, with Nicov leaning in for the moment. The following month, they appeared together again at Los Angeles International Airport, dressed casually, signaling the relationship was still very much intact.
In November 2024, Penn and Nicov made their red carpet debut at the 21st Marrakech International Film Festival in Morocco, where Penn received a career achievement award.
One of the more recent times the pair were last seen together was at the 78th annual Cannes Film Festival in May 2025.
