Sean Penn, 64, Faces Jokes for Dating Woman Younger Than His Daughter

Sean Penn, the 64-year-old Oscar-winning actor, has become the subject of playful mockery from friends who’ve jokingly dubbed him a “wrinkled prune.” The reason? His latest romance with 30-year-old Valeria Nicov, who happens to be three years younger than his own daughter, Dylan, who is 33. This age difference has certainly raised eyebrows, especially given the typical landscape of Hollywood relationships. Reports suggest that Penn’s friends can’t help but rib him for looking like a “dried-up prune” next to his youthful new partner.

According to insiders, while Penn’s appearance continues to show the telltale signs of aging, his choices in romantic partners seem to defy time, as he opts for women who are notably younger. One source commented on his dynamic, stating that Penn’s controlling nature often plays into these relationships, allowing him to feel dominant and youthful in contrast to his more mature self. They remarked on Penn’s desire to present himself as a “cool guy” who can attract younger women, despite the surrounding laughter and skepticism.

This new couple was first seen together in September, not long after Penn’s divorce from actress Leila George, who is just 32. Their five-year marriage came to an end in 2022. The disparity in age doesn’t just stir gossip; it also invites commentary from experts. Dr. Carole Lieberman, a well-known psychiatrist, weighed in on these types of relationships. She explained that while some older man-younger woman pairings stem from genuine affection, others raise red flags, often reflecting unhealthy dynamics where the older man seeks validation through a younger partner.

Lieberman, who does not have a therapeutic relationship with Penn, highlighted his past patterns of controlling behavior toward his partners. She suggested that the pursuit of younger women can sometimes serve as a misguided way for older men to affirm their desirability and virility. In her view, Penn’s excuses for past relationship struggles, such as attributing his issues to the stress of current events, are merely deflections.

Sean Penn’s latest romance continues to attract attention not just for its age difference but also for the implications it brings about his character and relationship history. As intriguing developments unfold in Hollywood, this pairing adds another colorful chapter to the narrative of celebrity love stories, filled with twists, age gaps, and societal commentary.