Sean Penn’s turbulent romantic history, including his relationships with Charlize Theron who once described him as “the love of my life,” showcases a pattern of passionate, intense connections spanning decades. From Hollywood marriages to high-profile breakups, his love life remains a subject of fascination, with his recent romance adding a new chapter to the saga.
Early Romance: The Relationship with Elizabeth McGovern
Sean Penn’s early romantic life featured a notable relationship with Elizabeth McGovern, known for her acclaimed roles and Golden Globe nominations. The two met while filming the 1984 romantic comedy Racing with the Moon, igniting a relationship that became on-again, off-again during the mid-1980s. Although the pair became engaged, their romance ultimately faltered.
Reflecting on their time together during a 2010 interview, McGovern described the relationship as significant yet draining, highlighting the persistent drama that surrounded Penn’s life:
“there’s drama to the way Sean lives every bit of his life”
—Elizabeth McGovern, Actress
“not someone who breathes drama every minute of the day.”
—Elizabeth McGovern, Actress
“I didn’t want to get married, but he did — or at least he said he did… I couldn’t sustain it… We also wanted to do different things. He likes to pretend he’s not really a Hollywood person, but he is.”
—Elizabeth McGovern, Actress
This early relationship revealed how differing personal priorities and Penn’s complex lifestyle contributed to their eventual split.
Marriage and Turmoil: Sean Penn and Madonna
Following his split from McGovern, Penn quickly became involved with another major star, Madonna. Their whirlwind romance began on the set of her “Material Girl” music video in early 1985, leading to a swift marriage by August that year. Although they collaborated on the film Shanghai Surprise and she dedicated her album True Blue to him, the marriage was fraught with difficulties.
Madonna filed for divorce twice, initially in late 1987 and again in January 1989. During this period, allegations surfaced accusing Penn of domestic violence; however, Madonna later vehemently denied these claims:
“completely outrageous, malicious, reckless, and false”
—Madonna, Singer
Their relationship, marked by both passion and conflict, ultimately ended legally in 1989 after repeated attempts at reconciliation.
The Long and Winding Road with Robin Wright
After parting from Madonna, Penn began a relationship with actress Robin Wright later in the 1980s, which evolved into one of his longest and most publicly detailed partnerships. The two had two children together: daughter Dylan Frances, born in 1991, and son Hopper Jack, born in 1993.
Their relationship was complex, marked by a break in 1995 when Penn briefly dated singer Jewel. Penn and Wright eventually married on April 27, 1996, but faced multiple separations and reconciliations throughout the years. They filed for divorce in 2007 but withdrew it, only for Penn to file for legal separation in 2009. Wright’s final divorce filing in August 2009 ended the tumultuous chapter.
Speaking about their repeated efforts to maintain the family unit, Wright explained:
“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.”
—Robin Wright, Actress
Their divorce concluded in mid-2010, with custody arrangements and support details settled privately.
A Brief Affair: Penn and Singer Jewel
During the hiatus in Penn’s relationship with Wright in 1995, he became linked romantically to singer Jewel. After witnessing her singing on Late Night with Conan O’Brien, Penn invited Jewel to write a song for his film The Crossing Guard and even toured after her. Jewel recounted a humorous start to their connection in her memoir:
“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.’”
—Jewel, Singer
This flirtation, however, was short-lived as Penn returned to Wright, ending the fling.
A Short-Lived Romance with Scarlett Johansson
In 2011, Sean Penn entered one of his most publicized but brief relationships with Scarlett Johansson. Despite their 24-year age difference, the couple was spotted frequently together in Los Angeles, attending events including the White House Correspondents Dinner and even traveling to Cabo San Lucas, Mexico.
Their romance was described as a whirlwind but lasted only a few months before they parted ways, with the reasons for their split remaining private.
Charlize Theron: The Love of His Life
One of Penn’s most intense and talked-about relationships was with Charlize Theron, a long-time friend turned partner. The pair’s romance began around Halloween 2013 when they were seen together at a party. By early 2015, Theron openly praised Penn, calling him:
“He’s my partner, he’s the love of my life.”
—Charlize Theron, Actress
Despite this declaration, the couple’s relationship ended by mid-2015. Although rumors circulated about an engagement, Theron denied them. She later addressed the breakup candidly, critiquing the media’s tendency to complicate simple separations:
“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. […] 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.”
—Charlize Theron, Actress
This clarity emphasized how tabloid speculation often distorts the realities of personal relationships.
Marriage to Leila George and Its Challenges
In a relationship marked by a considerable age gap of 32 years, Sean Penn and Leila George’s romance began in 2016 when George was just 24. Their union culminated in marriage in July 2020 amid the global COVID-19 pandemic. However, the marriage was strained, with Penn later admitting fault in its downfall.
During an interview, Penn expressed regret about neglect and personal struggles contributing to the breakup, revealing:
“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… 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.”
—Sean Penn, Actor
Their marriage ended after over a year, with George filing for divorce in late 2021 and the proceedings concluding in April 2022.
Sean Penn’s Current Relationship: Dating Olga Korotyayeva
Despite the ups and downs of his earlier love life, Sean Penn continues to seek companionship. Since June 2023, he has been dating actress Olga Korotyayeva, 45, with whom he was first seen in Rome. The couple’s public outings, including dog walks captured in October 2024, highlight a steady relationship despite their 17-year age difference.
This latest chapter illustrates Penn’s ongoing search for connection amid a life marked by both personal and professional intensity.
Sean Penn’s romantic history, with its blend of fervent passion, public scrutiny, and personal challenges, underscores the complexities that come with love in the spotlight. His relationships with figures like Charlize Theron and Madonna not only captivated the public but also reflected the emotional turbulence of balancing fame and intimacy. As he moves forward with Olga Korotyayeva, it remains to be seen how his evolving love story will unfold in the years to come.
Our Reader’s Queries
Q. What illness did Charlize Theron have as a child?
A. Theron went to Putfontein Primary School, where she felt she didn’t really belong. As a child, she often had jaundice. The antibiotics she took caused her upper baby teeth to decay, leading to their surgical removal.
Q. Does Charlize Theron have OCD?
A. In a radio interview, Charlize Theron, a well-known actress who won an Oscar, talked about her past battles with OCD. She mentioned her need for things to be in perfect order and how thinking about misplaced items can make it hard for her to sleep.
