Sean Penn's Dating History: From Madonna to Charlize Theron

Elizabeth McGovern

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.

Madonna

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. 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.

Robin Wright

Penn and Wright got together shortly after his divorce from Madonna, and the couple welcomed daughter Dylan in 1991 and son Hopper in 1993. They married in 1996 and remained together until they divorced in 2010.

Though their 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 same ethical views on parenting, including the continuing parenting of adult children."

Jewel

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 later marry Wright in 1996.

Scarlett Johansson

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.

The couple also attended a White House Correspondents' Dinner party in Washington, D.C., in late April 2011, where they were seen holding hands. They were also seen together several times in L.A. that spring; by June 2011, PEOPLE reported they were no longer together.

Charlize Theron

Penn and Theron began seeing each other in 2013; they split 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 told Esquire 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's 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------ crazy story or some crazy drama," she told WSJ. Magazine. "And the f------ ghosting thing, like literally, I still don't even know what it is."

Leila George

Penn wed the Australian actress in July 2020 in an intimate ceremony at home. Just over one year later, George filed for divorce, and the couple finalized their divorce in 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 told Hollywood Authentic in 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."