Your Guide to Sean Penn's A-List Relationship History
Sean Penn has quite an eventful romantic history, including three marriages and many high-profile girlfriends (Charlize Theron, anyone?).
His first marriage was to Madonna, and the two reportedly enjoyed some high highs and low lows together; his second marriage was to Robin Wright, with whom he spent nearly 20 years and had two kids (now-adult children Dylan and Hopper); and his third marriage was to Leila George, who filed for divorce in October 2021, only a year after the two tied the knot. And that's to say nothing of Penn's many relationships that didn't end in wedding bells.
Here's a closer look at the Oscar-winning actor's marriage and relationship history.
Who is Sean Penn dating now?
The Dead Man Walking actor is currently dating actress Olga Korotyayeva. They've been together since at least June 2023, when they were spotted vacationing in Rome. As recently as October of this year, they were seen holding hands on a dog walk.
Who is Sean Penn's girlfriend Olga Korotyayeva?
Korotyayeva is an actress who's starred in a handful of movies since 2010. Her latest role, according to IMDB, was in the Canadian crime series C*A*U*G*H*T. She appears to be a relatively private figure and doesn't have public social media accounts.
What is the age difference between Sean Penn and his current girlfriend?
Penn and Korotyayeva have a roughly 17-year age difference.
How many marriages has Sean Penn had?
Penn has been married three times.
Who are Sean Penn's ex-wives?
Madonna (1985-1989)
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Madonna and Penn were married for four years from 1985 to 1989. They first met on the set of the movie Shanghai Surprise.
Their relationship was known for its ups and downs, and Penn was accused of physically assaulting Madonna at least twice. But the singer later denied the allegations completely as part of a defamation suit Penn filed against Lee Daniels.
The backstory: In December 2015, Penn brought a $10 million suit against Daniels because while defending his Empire star Terrence Howard (who came under heavy fire after admitting to hitting his wife), Daniels said his friend "ain’t done nothing different than Marlon Brando or Sean Penn." To support Penn's case, Madonna submitted a written statement.
"I am aware of the allegations that have surfaced over the years accusing Sean of incidents of physical assault and abuse against me," she said. "Specifically, I am aware of the allegations concerning an alleged incident that occurred in June 1987, whereby (according to tabloid reports) Sean allegedly struck me with ‘a baseball bat’. I know the allegations in those and other reports to be completely outrageous, malicious and false."
She added, "I am also aware of allegations concerning an incident that occurred in December 1989, which purportedly resulted in Sean’s arrest for domestic assault and battery against me. I know those allegations to be false. While we certainly had more than one heated argument during our marriage, Sean has never struck me, ‘tied me up’ or physically assaulted me, and any report to the contrary is completely outrageous, malicious, reckless and false."
Daniels later issued an apology, which Penn publicly accepted.
Related: 100 Best Madonna Songs of All Time, Ranked
Robin Wright (1996-2010)
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Wright and Penn began a relationship soon after he and Madonna divorced. Their daughter, Dylan, was born in 1991 and their son, Hopper, followed in 1993. The two decided to get married three years later.
Wright later told the Telegraph that she and Penn tried to make things work for their children for a long time. As she put it, "Divorce in and of itself, and with children, is devastating. Worse than that. One of the reasons why we got back together and broke up so much was trying to keep the family together. If you've got kids, it's a family, and you try again, and you try again. We did that for a long time."
Leila George (2020-2021)
Photo by Rodin Eckenroth/Getty Images
Penn and Australian actress Leila George began dating in 2016 and decided to get married in July 2020 during the COVID-19 pandemic.
Penn later admitted that their divorce a year later was his fault. While speaking with Hollywood Authentic, he said, "There's a woman who I'm so in love with, Leila George, who I only see on a day-to-day basis now, because I f----d up the marriage. We were married technically for one year, but for five years, I was a very neglectful guy."
He continued, "I was not a f---ing cheat or any of that obvious s--t, but I allowed myself to think that my place in so many other things was so important, and that included my place in being totally depressed and driven to alcohol and Ambien at 11 o'clock in the morning, by watching the news, by watching the Trump era, by watching it and just despairing."
Who does Sean Penn have children with?
Penn and his second wife, Robin Wright, share two children.
While speaking about co-parenting their now-adult kids, Penn somewhat cryptically told Marc Maron, "We don’t not get along. We have very separate relationships with our kids at this point and it seems to work better that way because they are making their own decisions. As it turned out, she and I did not share the same ethical views on parenting, including the continuing parenting of adult children."
How long were Charlize Theron and Sean Penn together?
Theron and Penn dated from 2013 to 2015. Their decades-long friendship turned romantic around Halloween 2013, when they were spotted at a party together.
At the beginning of 2015, Theron told Elle UK of Penn, "He's my partner, he's the love of my life." However, something shifted between the two by June of the same year, when their breakup was announced.
A year later, Theron set the record straight on their split and rumors that she had ghosted the actor. She told WSJ Magazine, "There is this need to sensationalize things. When you leave a relationship there has to be some f---ing crazy story or some crazy drama. And the f---ing ghosting thing, like literally I still don’t even know what it is."
She added, "It’s just its own beast. We were in a relationship and then it didn’t work anymore. And we both decided to separate. That’s it."
Did Sean Penn date Scarlett Johansson?
Johansson and Penn briefly dated for a few months in 2011. It's unclear why they separated, but their age difference (Penn was 50 to Johansson's 26 at the time) might have played a role.
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Did Sean Penn date Elizabeth McGovern?
Penn dated the Downton Abbey star on-and-off in the mid-eighties, after meeting on the set of the 1984 movie Racing with the Moon. "I didn't want to get married, but he did—or at least he said he did," McGovern once told the Daily Mail, adding that the relationship was "so exhausting."
"I couldn't sustain it," she said. "We also wanted to do different things. He likes to pretend he's not really a Hollywood person, but he is."
Did Sean Penn date Jewel?
An early adopter of Jewel's music, Penn reportedly reached out to the singer-songwriter after he saw her perform on Late Night with Conan O'Brien in 1995 (he and Robin Wright were on a break).
"One day, my dad came to find me, saying, 'Jewel, you must be getting some kooky fans out there in the Lower 48. Some guy just prank-called and said he was Sean Penn,'" she wrote in her book Never Broken: Songs Are Only Half the Story (via People).
Although she described him as "a fantastic flirt," she adds that they didn't last long. The stuff of love songs!
