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Sean Penn's Relationship History, From Madonna to Leila George – Yahoo Entertainment

The Downton Abbey star met Penn early on in her career, on the set of their 1984 movie Racing with the Moon.
They quickly fell in love and got engaged, according to the Daily 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,” the Ordinary People star 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.
The pop icon and the actor were married from 1985 to 1989. The pair have been through a number of ups and downs, including Madonna expressing that she was “still in love” with the actor during a charity gala at Art Basel in 2016. Outside of the gala, Madonna has since defended her ex-husband from reports of previous domestic violence, denying any accusations including 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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Penn and Wright got together shortly after his divorce and welcomed daughter Dylan in 1991 and son Hopper in 1993. They married in 1996, and remained together until 2010.
Though their divorce wasn’t amicable, Penn has said, he and Wright now are 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 same ethical views on parenting, including the continuing parenting of adult children.”
In 1995, Penn saw an early performance by singer-songwriter Jewel on Late Night with Conan O’Brien and reached out to her at her family’s home in Alaska to arrange a meeting.
“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 recalled in her book Never 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 marry Wright the next year.
The duo dated circa 2011, when they were spotted on a romantic getaway to Cabo San Lucas, Mexico, after being seen grabbing lunch together in Los Angeles.
The couple also attended a White House Correspondents’ Dinner party in Washington D.C. that April, where they were seen holding hands. They were seen together a number of times in L.A. that spring; by June 2011, PEOPLE reported they were no longer together.
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Though twice-divorced, the actor claimed in an interview conducted while he was dating Theron that he’d consider his next marriage his first. (The pair first began seeing each other in 2013; they split in 2015.)
“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 told Esquire U.K. in 2015. “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 The 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 told Howard Stern. “We never moved in. I was never 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—ing crazy story or some crazy drama,” she told WSJ Magazine. “And the f—ing ghosting thing, like literally, I still don’t even know what it is.”
Penn wed the Australian actress in July 2020, in an intimate ceremony at home. Just over one year later, George, 29, filed for divorce.
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.

The actor's third wife, Leila George, just filed for divorce after a year of marriage. Look back at the actor's high-profile love life in photos
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