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Thespian Sean Penn has encountered romance several times with some of Tinseltown’s most celebrated women. While mainly recognized for his parts in acclaimed movies such as Milk, I Am Sam, and The Interpreter, Sean has likewise been the main attraction in his three former spouses’ lives. Continue scrolling to get acquainted with the women who have considered Sean their husband throughout the years.
Madonna
Madonna & Sean Penn were married from 1985 to 1989. (Jim Smeal/Shutterstock)
The iconic Madonna wedded Sean in 1985, when her music career was taking off. Sean and the “Like a Virgin” artist were a couple for about four years until the famous twosome opted to separate. On the fourth of December, 1987, Madonna submitted the paperwork for a divorce from Sean, only to rescind it a mere 12 days afterwards, according to Today In Madonna History. It seemed that everything was okay again, until the pop superstar requested a divorce again on the fifth of January, 1989. The formal request apparently mentioned “unresolvable conflicts” as the justification for the split.
Approximately three decades later in 2016, Madonna and Sean made an appearance together in Miami at her charity event occurring at Art Basel. During this gathering, Madonna proclaimed “I’m still in love with you” to her former partner of 27 years. At that point, Madonna and Sean auctioned off some of their monochrome wedding photos for a charitable cause. It’s delightful to realize there was no animosity between them!
Robin Wright
Robin Wright & Sean Penn were married from 1996 to 2010. (Chris Pizzello/AP/Shutterstock)
Following his parting from Madonna, Sean proceeded to marry Princess Bride actress Robin Wright, 56, seven years afterward in 1996. His relationship with Robin was his most enduring, seeing as the pair remained with each other for a total of 14 years before divorcing in 2010. Even though the former couple broke up 12 years prior, they continue to stay connected because of their mutual children.
Before getting hitched, Robin and Sean welcomed their daughter, Dylan Penn, in 1991, and subsequently welcomed their only son, Hopper Penn, in 1993. Subsequent to the split, Robin moved forward, marrying her spouse, Clement Giraudet. Her first husband, Dane Witherspoon, passed away in 2014 at the age of 56.
Leila George
Leila George (L) & Sean Penn were married from 2020 to 2022. (Vianney Le Caer/AP/Shutterstock)
Sean uncovered affection for a third time when he married Leila George in 2020. Prior to meeting Leila, the Milk performer also went out with Oscar recipient Charlize Theron from 2013 until 2015. His nuptials with Leila happened following an alleged four-year dating period, and it was brief, seeing as the former partners brought their marriage to an end in October of 2021.
It was the Aussie actress who submitted the separation request in Los Angeles at that time, just a year after they tied the knot. Sean and his previous sweetheart had a digital Zoom ceremony in the course of the initial COVID-19 lockdown of 2020. Afterward, in June of 2022, hardly two months after they made their separation official, Sean and Leila were observed having a meal together in Santa Monica. Some breakups have a friendly ending after all!