Sean Penn's Massive Age Gap With His Girlfriend Beats Karoline Leavitt & Her Husband

Since love is blind, you can't be too surprised when two people in the throes of it blatantly ignore the age gap between them. While a lot of people wouldn't even consider dating someone from a completely different generation, clearly, Sean Penn isn't one of them. The Oscar-winning actor is reportedly dating Valeria Nicov, who is a whopping 35 years younger than him. Not that he was trying, but Penn managed to give Karoline Leavitt a run for her money, relationship-wise.

The White House press secretary has made headlines several times due to the age gap between Leavitt and her husband, Nicholas Riccio, who is 32 years her senior. Now, the Trump staffer can even say that the age gap between them isn't even that big, and cite Penn as an example. In case you missed it, Penn and Nicov went public with their relationship in 2024, after Page Six spotted the couple kissing in public in Madrid. 

Nicov is a Moldovan actor and model who hasn't starred in any major productions at the time of writing. Penn hasn't spoken publicly about his relationship, so we don't know what drew them to each other and what their thoughts are on their age gap. But, judging by the photos, Penn and Nicov don't seem worried about it. Shortly before they went public, Penn told the New York Times that being single made him happy on a daily basis.

In stark contrast to Sean Penn, White House Press Secretary Karoline Leavitt has discussed the significant age difference between herself and husband Nicholas Riccio on several occasions. Due to her position, the Trump staffer frequently has to answer tough questions. But, in 2025, she gladly opened up about her marriage on "The Megyn Kelly Show." As Leavitt acknowledged, "It's a very atypical love story but he's incredible." She gushed, "He is my greatest supporter, he's my best friend and he's my rock. He's built a very successful business himself so now he's fully supportive of me building my success in my career."

Valeria Nicov is a somewhat low-profile romance for Sean Penn, who has a complicated history with Madonna, and was also married to fellow actor Robin Wright. Likewise, Penn's relationship with Charlize Theron remains a hot topic. Now that the "One Battle After Another" star is of a certain age, chances are that he has a different perspective on life and this translates to the kind of relationship he's interested in too. Maybe Nicov is an old soul, which could explain why she connected with a man who is so much older than her. Or maybe the couple's love story was much like Leavitt's and Riccio's. 

According to the White House press secretary, they were slowly drawn to each other and remained friends for quite some time before things turned romantic. If Penn was really happy to be single in 2024, he probably wasn't thinking about entering a relationship until Nicov came along. It's not exactly unheard of, but it doesn't mean that we won't be surprised every time we see a picture of either age-gap couple together.