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▲Putting an end to the seemingly baseless rumors that he was dating Stacey Nelkin was Penn's romantic involvement with actress Peggy Trentini.
▲Between 1983 and 1984, Penn fell for actress Elizabeth McGovern. They were both in the 1984 film 'Racing with the Moon.'
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The actress, known for works like 'Red Sonja,' 'Cobra,' and 'Rocky IV' (pictured), wrote about her romance with Penn in her autobiography.

▲Penn's 1984 relationship with the actress didn't last long.
▲The Hollywood heavyweights reportedly dated in 1984, and though it didn't last long, they later starred together in 1995's 'Dead Man Walking.'
▲After Penn's infamous year of public violent outbursts, and being sentenced to jail time, Madonna filed for divorce, but then withdrew the papers for an unknown reason.
▲And she accepted, but changed her mind soon after, citing her young age and deciding to prioritize her career. "Married Sean?" said McGovern in an interview, rolling her eyes. "I think I was the lucky one to do what I did."
▲Australian supermodel Elle Macpherson entered the picture in 1996. According to the New York Post, the two were seen getting cozy in an NYC restaurant: "They kissed between puffs, and acted like no one else was in the room."
▲The on-and-off couple first got together in August 1990, dated for six years, and married on April 27, 1996.
▲Though the dates are murky (some say it was during an off-period of seeing Robin Wright), Penn dated singer Jewel for a short time. He reportedly first called her up to write a song for his movie 'The Crossing Guard.' She wrote about him sweetly in her book 'Never Broken – Songs Are Only Half the Story.'
▲Their union went on to last 14 more years, with the couple announcing their separation and reconciliation a few times over the course of their marriage, then ultimately filing for divorce in July 2010.
▲In 1987, tabloids said Penn hit her with a baseball bat, and in January 1989, tabloids claimed Madonna was again beaten by her husband. Later that year, Madonna filed for divorce again, and by September 14, 1989 they were no longer husband and wife.
▲In 2015, Madonna released a statement about the allegations, calling them "completely outrageous, malicious, reckless, and false," even though The Guardian reports that she had gone to the sheriff’s office and made the complaint that Penn had assaulted her in December 1988.
▲Their first child is Dylan Frances, a daughter. Two years later, their son Hopper Jack was born.
▲Penn is said to have dated activist and supermodel Petra Nemcova while he was on a break from his now ex-wife Robin Wright back in 2008. The two were rumored to be back together in 2012, though it was short-lived.
▲In 2012, Penn told Esquire, "There is no shame in 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.” Ouch!
▲In 2009, Penn was rumored to have gotten hot and heavy with the actress at the Sunset Tower Hotel's bar. Portman, however, vehemently denied the reports: "I normally do not respond to rumors about my private life, however, this repeatedly fabricated story has forced me to do so.”
▲Between August 2009 and September 2010, Penn was linked to American model Jessica White, who is famous for several of Sports Illustrated's Swimsuit Issues from 2003 to 2008.
▲Between February and June 2011, the actors were spotted together several times, but Penn broke if off, reportedly claiming to not want anything serious.
▲In 2012, Penn was rumored to have dated Argentine actress and model Calu Rivero.
▲Penn was also spotted at dinner with the Haitian actress and former fashion model in 2011, and though rumors flooded there was no confirmation of their romantic relation.
▲Also in 2011, Penn started dating Shannon Costello, the former communications director of his J/P Haitian Relief Organization, who is 25 years his junior.
▲In December 2013 the two started dating, nearly a decade after posing together as winners of Best Actress and Best Actor at the Oscars in 2004. By November 2014, they were engaged.
▲Though it seemed promising—and Penn had even told a reporter, "Charlize is not my girlfriend. She's the love of my life"—by June 2015, it was all over.
▲In late 2016, Penn started dating the daughter of actor Vincent D'Onofrio (pictured), Leila George, then 24 years old, who is also an actress.
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More than two decades exist between George and Penn. Penn is also just one year younger than her father, and George is one year younger than Penn's daughter Dylan (pictured). Who knows if that had anything to do with their split—their divorce was finalized in April 2022.

▲

Us Weekly was told by a source that less than two weeks after splitting from Theron, Penn went out to dinner with actress Minka Kelly and some mutual friends, which was supposedly their first date, in a group setting, just to see how things would go. Their romantic involvement was never confirmed.

See also: Celebrity couples you totally forgot were engaged

▲

Penn was reportedly spotted going on several dates with the Italian actress in 2011, but the whole thing fizzled out.

▲

The two reportedly met in February 1985 and married a few months later, on August 16, 1985. They also co-starred in 'Shanghai Surprise' as newlyweds.

▲

Sean Penn's reputation in Hollywood is a mixture of high regard for his profound work in films like 'Milk' and 'Mystic River,' along with some reticence for his eccentrically grumpy off-screen persona. He's gone from strength to strength in acting, and gone from controversy to controversy in headlines, but there has been one constant among it all: his affinity for talented women.

Penn's private life has been more of a hot topic than many of his films in recent years, and there's good reason for it, what with his romantic journey among the likes of Susan Sarandon and Charlize Theron, leading to his most recent, and short-lived, marriage to Leila George, who is one year younger than his own daughter.

The actor has cultivated a wild, experimental nature over the years, and has proposed to four other women in his past! Click through this gallery to see all the women Penn has romanced, or has been rumored to romance, over the years.

A deep dive into Sean Penn's star-studded romantic past

The Oscar winner turns 62 this August 17

17/08/22 por StarsInsider

CELEBRITY Relationships

Sean Penn's reputation in Hollywood is a mixture of high regard for his profound work in films like 'Milk' and 'Mystic River,' along with some reticence for his eccentrically grumpy off-screen persona. He's gone from strength to strength in acting, and gone from controversy to controversy in headlines, but there has been one constant among it all: his affinity for talented women.

Penn's private life has been more of a hot topic than many of his films in recent years, and there's good reason for it, what with his romantic journey among the likes of Susan Sarandon and Charlize Theron, leading to his most recent, and short-lived, marriage to Leila George, who is one year younger than his own daughter.

The actor has cultivated a wild, experimental nature over the years, and has proposed to four other women in his past! Click through this gallery to see all the women Penn has romanced, or has been rumored to romance, over the years.

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