Shriveled Sean Penn, 64, 'Looking Like Wrinkled Prune Joke' To Pals By Flaunting New Girlfriend 3 Years Younger Than His Daughter Dylan
64-year-old Sean Penn is mocked as a 'wrinkled prune' by pals while flaunting his new girlfriend, 3 years younger than his daughter Dylan.
Dec. 25 2024, Published 4:00 p.m. ET
Over-the-hill Lothario Sean Penn's latest girlfriend is three years younger than his 33-year-old daughter, Dylan, RadarOnline.com can reveal.
Sources said Penn, 64, looks like a "dried-up prune" next to his new galpal, 30-year-old Valeria Nicov. Even in a town where May-December romances are common, the gaping-wide age gap has caused a lot of eye-rolling.
Penn sparks eye-rolls with new girlfriend, 30, who's younger than his daughter.
An insider said: "Sean gets more grizzled and gray, but his partners get younger and more fresh-faced.
"He's known to be very controlling, and dating a much younger woman puts him in a dominant position. He wants to be seen as this cool guy who can catch the hotties, but everyone around him knows it's a joke."
Penn and Nicov emerged as a couple in September, two years after his 2022 divorce from actress Leila George, 32, who was with the actor for five years.
Penn trades grizzle for control, dating a younger woman after divorce.
As RadarOnline previously reported, he was drinking and taking the sleep aid Ambien at 11 a.m. because he was "totally depressed" watching the news about Donald Trump's presidency.
Beverly Hills celebrity psychiatrist Dr. Carole Lieberman told RadarOnline.com: "Some older man-younger woman relationships are based upon love, but others are based upon unhealthy reasons. Many times, the man uses the younger woman as proof to the world he's still handsome and sexy."
Penn's new romance raises eyebrows – psychologist reveals the darker side of older man-younger woman relationships.
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Lieberman, who hasn't treated Penn, added: "Sean has a history of being controlling towards women, and it's often easier to control a younger woman. He expects his girlfriends and wives to simply follow along with whatever he wants.
"Blaming his neglect of Leila on his despair over 'the Trump era' is ridiculous and a poor excuse."
