Sean Penn EXCLUSIVE: Actor, 61, spotted out for the first time after estranged wife Leila George, 29, filed for divorce following 15-month marriage
- His estranged wife, Leila George, 29, officially filed for divorce on Friday after 15 months of marriage
- No details of what led to the split have been provided at this time
- The couple wed in July 2020 following four years of dating
- He was previously married to Robin Wright from 1996 to 2010, with whom he shares two children, and Madonna from 1985 to 1989
- Their relationship had its ups and downs as a source told PEOPLE in August 2020 that prior to their marriage he had to 'win her back'
Sean Penn was spotted out for the first time just days after his estranged wife, Leila George, filed for divorce following 15 months of marriage.
The 61-year-old actor stepped out wearing a dapper black suit as he visited a friend in the Los Angeles area on Saturday afternoon.
Penn was no long wearing a wedding ring after George filed legal documents to end their union on Friday following four years of dating and only one year of marriage, according to documents filed in the Los Angeles County Superior Court.
![Out and about: Sean Penn was spotted out for the first time just days after his estranged wife, Leila George, filed for divorce following 15 months of marriage](https://i.dailymail.co.uk/1s/2021/10/17/17/49286913-0-image-a-1_1634488951158.jpg)
Out and about: Sean Penn was spotted out for the first time just days after his estranged wife, Leila George, filed for divorce following 15 months of marriage
![Ring-free: Penn was no long wearing a wedding ring after George filed legal documents to end their union on Friday following four years of dating and only one year of marriage, according to documents filed in the Los Angeles County Superior Court](https://i.dailymail.co.uk/1s/2021/10/17/17/49286911-0-image-a-2_1634489014038.jpg)
Ring-free: Penn was no long wearing a wedding ring after George filed legal documents to end their union on Friday following four years of dating and only one year of marriage, according to documents filed in the Los Angeles County Superior Court
Sean — who was previously married to Robin Wright and Madonna — sported a black blazer with matching slacks and a crisp white button down.
The two-time Academy Award-winner wore a black tie and dress shoes to match as he parked his car outside of a friend's house in LA.
His dark brown hair was slicked back with salt and pepper strands, and he went clean shaven for the outing.
![Out and about: The 61-year-old actor stepped out wearing a dapper black suit as he visited a friend in the Los Angeles area on Saturday afternoon](https://i.dailymail.co.uk/1s/2021/10/17/17/49287165-10101199-image-a-19_1634489231031.jpg)
Out and about: The 61-year-old actor stepped out wearing a dapper black suit as he visited a friend in the Los Angeles area on Saturday afternoon
![Dressed up: Sean ¿ who was previously married to Robin Wright and Madonna ¿ sported a black blazer with matching slacks and a crisp white button down](https://i.dailymail.co.uk/1s/2021/10/17/17/49287197-10101199-image-a-20_1634489334338.jpg)
Dressed up: Sean — who was previously married to Robin Wright and Madonna — sported a black blazer with matching slacks and a crisp white button down
The Australian actress, 29, — who wed Penn, 61, in July 2020 — filed divorce, according to TMZ.
It marks the end of Sean's third marriage after previously divorcing from House Of Cards actress Robin Wright in 2010 after 14 years together and Madonna in 1989 after four years together.
No details of what led to the split have been provided at this time, but their relationship was said to have had ups and downs before he proposed, as well as the star having a packed work schedule this summer.
Penn first confirmed he had married George last summer during a civil ceremony over zoom and shortly afterwards during a Late Night with Seth Meyers appearance he flashed a gold wedding band.
![Splitsville: Sean Penn's wife of just over a year, Leila George has filed for divorce from the actor (pictured together in January 2020)](https://i.dailymail.co.uk/1s/2021/10/16/01/49237697-10097997-image-a-101_1634345804986.jpg)
Splitsville: Sean Penn's wife of just over a year, Leila George has filed for divorce from the actor (pictured together in January 2020)
He told the host: 'We did a COVID wedding. By that, I mean it was a county commissioner on Zoom and we were at the house with my two children and her brother, and we did it that way.'
Their relationship had its ups and downs as a source told PEOPLE in August 2020 that prior to their marriage he had to 'win her back.'
'They got together and then they broke up, and Sean won her back,' said the insider. 'He realized he had made a mistake and when he felt he might lose her, he worked hard to get her back.'
![Last public outing: The couple were last seen out together on August 1 as they shopped at a Pavilions supermarket following lunch in Malibu](https://i.dailymail.co.uk/1s/2021/10/16/02/49237943-10097997-image-a-105_1634346564739.jpg)
Last public outing: The couple were last seen out together on August 1 as they shopped at a Pavilions supermarket following lunch in Malibu
'They got back together during COVID and became really close and got engaged a few months ago, early during quarantine.'
At 29, Leila is only a few months younger than his now 30-year-old daughter Dylan Penn, and only two years older than his son Hopper, 27.
Sean has long been a critic of political correctness in Hollywood, and in 2018 the star said he thought the #MeToo movement was 'too black and white' and aimed to 'divide men and women'.
In a podcast interview last year he also branded cancel culture in today's society 'ludicrous', adding that it 'feels very Soviet sometimes'.
Though his split details are unknown, Sean spent most of August and early September overseas promoting his film Flag Day with his daughter Dylan.
The couple's last public outing came in August as they went to a grocery store in Malibu, California.
On October 13, The I Am Sam actor was spotted out solo following dinner at Craig's without his wedding ring.
Sean first met Leila on the set of the movie The Last Face starring Javier Bardem and Charlize Theron and had said that it was love at first sight.
![It's over: The Australian actress, 29, - who wed Penn, 61, in July 2020 after four years of dating - filed divorce documents on Friday (pictured in January 2020)](https://i.dailymail.co.uk/1s/2021/10/16/01/49237449-10097997-image-a-89_1634345095868.jpg)
It's over: The Australian actress, 29, - who wed Penn, 61, in July 2020 after four years of dating - filed divorce documents on Friday (pictured in January 2020)
However the relationship had its ups and downs as a source told PEOPLE in August 2020 that prior to their marriage he had to 'win her back.'
'They got together and then they broke up, and Sean won her back,' said the insider. 'He realized he had made a mistake and when he felt he might lose her, he worked hard to get her back.'
'They got back together during COVID and became really close and got engaged a few months ago, early during quarantine.'
Prior to George, Penn had been in a two decade long relationship with Robin Wright and they were married for 14 of them.
![Second marriage: He was previously married to House Of Cards actress Robin Wright from 1996 to 2010 (pictured in February 2009)](https://i.dailymail.co.uk/1s/2021/10/16/02/49237719-10097997-image-a-106_1634347700963.jpg)
Second marriage: He was previously married to House Of Cards actress Robin Wright from 1996 to 2010 (pictured in February 2009)
![Tumultuous: The marriage had been very on-and-off and he had first filed to divorce the actress in December 2007 before they reconciled five months later; pictured 2007](https://i.dailymail.co.uk/1s/2021/10/16/02/49238205-10097997-image-a-107_1634348128139.jpg)
Tumultuous: The marriage had been very on-and-off and he had first filed to divorce the actress in December 2007 before they reconciled five months later; pictured 2007
The marriage had been very on-and-off and he had first filed to divorce the actress in December 2007 before they reconciled five months later.
In April 2009 the actor filed for divorce again, before he withdrew the motion just one month later.
However in August of that year, Wright filed for divorce and court records show that they were officially ruled divorced less than one year later, on July 22, 2010.
In 2012 Penn had dropped a bombshell while speaking to Esquire saying that he felt like he was never truly 'loved' by Wright or his first wife Madonna.
![Kids: Penn and Wright share two children: daughter Dylan, 30, (center) and son Hopper, 27 (left), and he had spent the majority of August doing press overseas for their film Flag Day](https://i.dailymail.co.uk/1s/2021/10/16/02/49238305-10097997-image-a-108_1634348346314.jpg)
Kids: Penn and Wright share two children: daughter Dylan, 30, (center) and son Hopper, 27 (left), and he had spent the majority of August doing press overseas for their film Flag Day
'There is no shame in my saying that we all want to be loved by someone. As I look back over my life in romance, I don't feel I've ever had that. I have been the only one that was unaware of the fraud in a few of these circumstances blindly.
'When you get divorced, all the truths that come out, you sit there and you go, What the f**k was I doing? What was I doing believing that this person was invested in this way? Which is a fantastically strong humiliation in the best sense. It can make somebody very bitter and very hard and closed off, but I find it does the opposite to me. '
In 2014 Wright told The Telegraph that the whole divorce process — especially with kids involved — was 'devastating.'
'Divorce in and of itself, and with children, is devastating. Worst 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.'
![First love: He was married to Madonna from 1985 to 1989 but the relationship was tumultuous and included several instances of physical and emotional abuse; pictured November 1987](https://i.dailymail.co.uk/1s/2021/10/16/02/49237679-10097997-image-a-109_1634349009804.jpg)
First love: He was married to Madonna from 1985 to 1989 but the relationship was tumultuous and included several instances of physical and emotional abuse; pictured November 1987
![Problematic: Just before the divorce, she filed a police report against him after he scaled their Malibu home and told her he owned her 'lock, stock, and barrel,' (pictured August 1986)](https://i.dailymail.co.uk/1s/2021/10/16/03/49237689-10097997-image-a-111_1634349837585.jpg)
Problematic: Just before the divorce, she filed a police report against him after he scaled their Malibu home and told her he owned her 'lock, stock, and barrel,' (pictured August 1986)
He was married to Madonna from 1985 to 1989 and had spoke about always having a special place in his heart for the Material Girl singer, saying in a 2018 Stephen Colbert appearance 'I love my first wife very much.'
In 2016 Madonna confessed that she was 'still in love' with the actor and jokingly offered to re-marry him if he paid $150,000 to her charity.
When she filed for divorce she cited irreconcilable differences. Prior to their wedding she seemed to think it was headed for trouble: 'His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen.'
The relationship was plagued by physical and emotional abuse, and she sought psychiatric help after the wedding.
In June 1987 he reportedly hit her across the head with a baseball bat but she refused to press charges.
Two years later she filed a police report after he scaled their Malibu home and told her he owned her 'lock, stock, and barrel,' and then proceeded to physically terrorize her, leaving her with injuries including a busted lip.
According to reports: 'When she told him she was leaving the house, he tried to bind her hands with an electric lamp and cord. Screaming and afraid, Madonna fled from the bedroom. What followed was a nine-hour ordeal which left her deeply shaken. Penn chased her into the living room, caught her and bound her to a chair with heavy twine. Then he threatened to cut off her hair.'
Penn was charged with felony domestic assault, but Madonna told the DA to drop the charges against him, though he eventually pleaded guilty to a misdemeanor. They split shortly thereafter.
![Rekindling? In 2016 Madonna confessed that she was 'still in love' with the actor and jokingly offered to re-marry him if he paid $150,000 to her charity (pictured 2013)](https://i.dailymail.co.uk/1s/2021/10/16/02/49237693-10097997-image-a-110_1634349192869.jpg)
Rekindling? In 2016 Madonna confessed that she was 'still in love' with the actor and jokingly offered to re-marry him if he paid $150,000 to her charity (pictured 2013)
Sean also dated actress Charlize Theron from 2013 to 2015, according to People.
The pair were friends for years, Charlize claimed in a Vogue interview in 2014.
'It just kind of naturally happened, and before I knew it, I was in something that was making my life better - the people who really love me can see the effect it has had on me,' she told the publication at the time.
The couple reportedly split in June 2015.
A few months prior to their breakup, it was claimed that Sean had proposed to Charlize in Paris.
![Exes: Sean also dated actress Charlize Theron from 2013 to 2015, according to People (pictured in 2015)](https://i.dailymail.co.uk/1s/2021/10/16/08/49245177-10097997-image-m-7_1634371087617.jpg)
Exes: Sean also dated actress Charlize Theron from 2013 to 2015, according to People (pictured in 2015)
The 44-year-old actress debunked these rumors during a interview with Howard Stern last summer.
She said: 'That's not true,' she said. 'That's not true. No. I did not 'almost get married to Sean.' That's such bulls**t. We dated. That was literally all we did.'
Theron continued: 'We dated and then we didn't date. It was a relationship, for sure. We were definitely exclusive, but it was for barely a year.
'We never moved in or… like, no, I wasn't gonna marry him. It was nothing like that.'
Charlize went on to emphasize the fact that she 'never wanted to get married,' saying that it has 'never been something that's important to me.'
![Having her say: She said of their relationship: 'We dated and then we didn't date. It was a relationship, for sure. We were definitely exclusive, but it was for barely a year'](https://i.dailymail.co.uk/1s/2021/10/16/08/49245179-10097997-image-m-8_1634371188628.jpg)
Having her say: She said of their relationship: 'We dated and then we didn't date. It was a relationship, for sure. We were definitely exclusive, but it was for barely a year'
It comes after in 2018 Sean criticized the #MeToo movement, asserting that it has divided men and women and that 'it's too black and white'.
The two-time Oscar winner revealed his feelings toward the movement during an interview at his home with actress Natascha McElhone, his co-star in the Hulu series 'The First'.
The show was set in the year 2030 and featured a heavily-female cast on a mission to Mars.
Interviewer Natalie Morales brought up the topic of the #MeToo movement by asking McElhone if she felt the use of so many strong female leads - including the actress's own role as 'an unapologetic visionary who oversees the mission' - was inspired by the crusade.
'Yeah, and for me in life, that's not unusual. I don't see that as aberrant,' McElhone said of the use of strong female characters.
'[However] I get that in TV and in a lot of our media, women haven't been depicted in that way, and I find that deeply disturbing.'
Penn disagreed with that assessment, saying: 'I'd like to think that none of it was influenced by what they call the movement of #MeToo.'
Penn went on: 'I think it's influenced by the things that are developing in terms of the empowerment of women who've been acknowledging each other and being acknowledged by men.
'This is a movement that was largely shouldered by a kind of receptacle of the salacious.'
![Opinions: It comes after in 2018 Sean criticized the #MeToo movement, asserting that it has divided men and women and that 'it's too black and white'](https://i.dailymail.co.uk/1s/2021/10/16/10/49247421-10097997-image-a-47_1634377715203.jpg)
Opinions: It comes after in 2018 Sean criticized the #MeToo movement, asserting that it has divided men and women and that 'it's too black and white'
Morales quickly prompted the star to explain what he meant by 'receptacle of the salacious'.
'Well, we don't know what's a fact in many of the cases,' Penn replied. 'Salacious is as soon as you call something a movement that is really a series of many individual accusers, victims, accusations, some of which are unfounded.
'The spirit of much of what has been the #MeToo movement is to divide men and women.'
Morales challenged: 'Women would say it's uniting women.'
Penn, who is known for his tendency to avoid media interviews, continued: 'I'm gonna say that women that I talk to, not in front of a camera, that I listen to, of all walks of life, that there's a common sense that is not represented at all in the discussion when it comes to the media discussion of it, the discussion where if Sean Penn says this, so and so's going to attack him for saying this, because of that.
'I don't want it to be a trend, and I'm very suspicious of a movement that gets glommed on to in great stridency and rage and without nuance. And even when people try to discuss it in a nuanced way, the nuance itself is attacked.'
He added: 'I think it's too black and white. In most things that are very important, it's really good to just slow down.'
In 2020 he then slammed cancel culture while speaking on the Conan O'Brien Needs a Friend podcast.
He said: 'It's ludicrous. What happened to 'let's talk about that now.' People can also be forgiven if they even need to be forgiven. It feels very Soviet sometimes.'
The 60-year-old actor then elaborated his opinion, 'When we're destroying careers like that, what are we really achieving? Or you look at politicians, I give a big nod to anyone that's willing to enter the public arena who is doing so because they give a damn.'
![Having his say: In 2020 he then slammed cancel culture while speaking on the Conan O'Brien Needs a Friend podcast](https://i.dailymail.co.uk/1s/2021/10/16/10/49247467-10097997-image-a-48_1634377816522.jpg)
Having his say: In 2020 he then slammed cancel culture while speaking on the Conan O'Brien Needs a Friend podcast
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