01of 07Elizabeth McGovernAlamyTheDownton Abbeystar metPennearly on in her career, on the set of their 1984 movieRacing with the Moon.They quickly fell in love and got engaged, according to theDaily Mail.“It was the frenzy of Sean’s feelings that overwhelmed me. It was also the first real experience of boys I’d had, which was kind of nice,” McGovern told the outlet. “In the beginning, it was fun. We were a similar age and in the same place professionally, so we were experiencing everything together.“Penn allegedly proposed to McGovern when she was 23 years old. “We lasted a couple of years on and off. I didn’t want to get married, but he did — or at least he said he did,” theOrdinary Peoplestar told the outlet.“It was so exhausting, 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,” she said.
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Elizabeth McGovern
Alamy
TheDownton Abbeystar metPennearly on in her career, on the set of their 1984 movieRacing with the Moon.
They quickly fell in love and got engaged, according to theDaily Mail.“It was the frenzy of Sean’s feelings that overwhelmed me. It was also the first real experience of boys I’d had, which was kind of nice,” McGovern told the outlet. “In the beginning, it was fun. We were a similar age and in the same place professionally, so we were experiencing everything together.”
Penn allegedly proposed to McGovern when she was 23 years old. “We lasted a couple of years on and off. I didn’t want to get married, but he did — or at least he said he did,” theOrdinary Peoplestar told the outlet.
“It was so exhausting, 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,” she said.
02of 07MadonnaVinnie Zuffante/Michael Ochs Archives/GettyThe pop icon and the actor were married from 1985 to 1989. The pair have been through a number of ups and downs, includingMadonnaexpressing that she was"still in love"with the actor during a charity gala at Art Basel in 2016. Beyond the gala, Madonna has since defended her ex-husband from reports of previous domestic violence,denying any accusations, including the 1987 and 1989 reports that he had previously assaulted her.“I know the allegations in those and other reports to be completely outrageous, malicious, reckless and false,” she said at the time, according to court documents.
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Madonna
Vinnie Zuffante/Michael Ochs Archives/Getty
The pop icon and the actor were married from 1985 to 1989. The pair have been through a number of ups and downs, includingMadonnaexpressing that she was"still in love"with the actor during a charity gala at Art Basel in 2016. Beyond the gala, Madonna has since defended her ex-husband from reports of previous domestic violence,denying any accusations, including the 1987 and 1989 reports that he had previously assaulted her.
“I know the allegations in those and other reports to be completely outrageous, malicious, reckless and false,” she said at the time, according to court documents.
03of 07Robin WrightRobin Wright and Sean Penn in 1996.Jeff Kravitz/FilmMagicPenn andWrightgot together shortly after his divorce from Madonna, and the couple welcomeddaughter Dylanin 1991 andson Hopperin 1993. They married in 1996 and remained together until theydivorced in 2010.Thoughtheir divorce wasn’t amicable, Penn has said he and Wright are now on decent terms for their kids.“We don’t not get along,” he added. “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 sameethical views on parenting, including the continuing parenting of adult children.”
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Robin Wright
Robin Wright and Sean Penn in 1996.Jeff Kravitz/FilmMagic
Penn andWrightgot together shortly after his divorce from Madonna, and the couple welcomeddaughter Dylanin 1991 andson Hopperin 1993. They married in 1996 and remained together until theydivorced in 2010.
Thoughtheir divorce wasn’t amicable, Penn has said he and Wright are now on decent terms for their kids.
“We don’t not get along,” he added. “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 sameethical views on parenting, including the continuing parenting of adult children.”
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Jewel
Jeff Kravitz/Filmmagic; Andrew Toth/Getty
“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,'” sherecalled in her bookNever Broken: Songs Are Only Half the Story.
Jewel said the actor was persistent in courting her and “a fantastic flirt,” but she was wary of becoming famous as an A-lister’s girlfriend rather than on their own merits, and they didn’t last long.
“He enjoyed putting me in situations that brought out the best in me, and he never ridiculed what was still so half-wild and messy about me,” she wrote of their brief time together.
He would later marry Wright in 1996.
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Scarlett Johansson
Frank Micelotta/PictureGroup
The actors briefly dated circa 2011 when they were spotted on a romantic getaway to Cabo San Lucas, Mexico, and after being seen grabbing lunch together in Los Angeles.
06of 07Charlize TheronJason LaVeris/FilmMagicPenn andTheronbegan seeing each other in 2013; theysplit in 2015. Though twice-divorced, the actor claimed while dating Theron that he’d consider his next marriage his first.“You say I’ve been married twice before, but I’ve been married under circumstances where I was less informed than I am today,” he toldEsquire U.K.“So I wouldn’t even consider it a third marriage, I’d consider it a first marriage on its own terms if I got married again.“Theron, who connected with Penn when he directed her in 2016’sThe Last Face,denied that it was as serious as people made it sound. “It was a relationship, for sure. We were definitely exclusive, but it was for barely a year,” she toldHoward Stern. “We never moved in. I wasnever going to marry him. It was nothing like that.“And to set the record straight,she didn’t “ghost” him.“When you leave a relationship, there has to be some f—— crazy story or some crazy drama,” she toldWSJ. Magazine.“And the f—— ghosting thing, like literally, I still don’t even know what it is.”
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Charlize Theron
Jason LaVeris/FilmMagic
Penn andTheronbegan seeing each other in 2013; theysplit in 2015. Though twice-divorced, the actor claimed while dating Theron that he’d consider his next marriage his first.
“You say I’ve been married twice before, but I’ve been married under circumstances where I was less informed than I am today,” he toldEsquire U.K.“So I wouldn’t even consider it a third marriage, I’d consider it a first marriage on its own terms if I got married again.”
Theron, who connected with Penn when he directed her in 2016’sThe Last Face,denied that it was as serious as people made it sound. “It was a relationship, for sure. We were definitely exclusive, but it was for barely a year,” she toldHoward Stern. “We never moved in. I wasnever going to marry him. It was nothing like that.”
And to set the record straight,she didn’t “ghost” him.
“When you leave a relationship, there has to be some f—— crazy story or some crazy drama,” she toldWSJ. Magazine.“And the f—— ghosting thing, like literally, I still don’t even know what it is.”
07of 07Leila GeorgeSean Penn and Leila George in January 2020.Michael Kovac/GettyPennwed the Australian actress in July 2020in an intimate ceremony at home. Just over one year later, Georgefiled for divorce, and the couplefinalized their divorcein April 2022.The pair have been romantically linked since 2016, and a friend of the actress told PEOPLE in August that they had reunited in 2020 after a period of being on and off.Penn toldHollywood Authenticin April 2022 that he’s"still in love with” George, calling her his “best friend in the world and definitely the most influential, inspiring person, outside of my own blood, that anybody could ask to have in their life.”
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Leila George
Sean Penn and Leila George in January 2020.Michael Kovac/Getty
Pennwed the Australian actress in July 2020in an intimate ceremony at home. Just over one year later, Georgefiled for divorce, and the couplefinalized their divorcein April 2022.
The pair have been romantically linked since 2016, and a friend of the actress told PEOPLE in August that they had reunited in 2020 after a period of being on and off.
Penn toldHollywood Authenticin April 2022 that he’s"still in love with” George, calling her his “best friend in the world and definitely the most influential, inspiring person, outside of my own blood, that anybody could ask to have in their life.”
source: people.com
