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

But she denied all the abuse allegations - 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.

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Jewel Kilcher - 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.'

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Elle Macpherson - 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."

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Robin Wright - The on-and-off couple first got together in August 1990, dated for six years, and married on April 27, 1996.

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They went the distance - Their union went on to last 14 more years, announcing their separation and reconciliation a few times over their marriage, then ultimately filing for divorce in July 2010.

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They had two children - Their first child is Dylan Frances, a daughter. Two years later, their son Hopper Jack was born.

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Penn's harsh reflection - 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!

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Petra Nemcova - 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.

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Natalie Portman - 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.”

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Jessica White - 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.

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

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Scarlett Johansson - Between February and June 2011, the actors were spotted several times, but Penn broke if off, reportedly claiming to not want anything serious.

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Garcelle Beauvais - 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.

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Shannon Costello - 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.

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Calu Rivero - In 2012, Penn was rumored to have dated Argentine actress and model Calu Rivero.

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Charlize Theron - 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.

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Called it off - 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.

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Minka Kelly - 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.

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Leila George - 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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Headline-grabbing age gap -

More than two decades exists between George, 27, and Penn, 59. Penn is also just one year younger than her father, and George is one year younger than Penn's daughter Dylan (pictured).

Check out these other celebs with age gaps you wouldn't believe.

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Peggy Trentini - Putting an end to the seemingly baseless rumors that he was dating Stacey Nelkin was Penn's romantic involvement with actress Peggy Trentini.

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Brigitte Nielsen -

The actress, known for works like 'Red Sonja,' 'Cobra,' and 'Rocky IV' (pictured), wrote about her romance with Penn in her autobiography.

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Elizabeth McGovern - 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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Barbara Hershey - Penn's 1984 relationship with the actress didn't last long.

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Susan Sarandon - The Hollywood heavyweights reportedly dated in 1984, and though it didn't last long, they later starred together in 1995's 'Dead Man Walking.'

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

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She filed for divorce - 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.

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Robin Wright - The on-and-off couple first got together in August 1990, dated for six years, and married on April 27, 1996.

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They went the distance - Their union went on to last 14 more years, announcing their separation and reconciliation a few times over their marriage, then ultimately filing for divorce in July 2010.

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They had two children - Their first child is Dylan Frances, a daughter. Two years later, their son Hopper Jack was born.

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Jessica White - 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.

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

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Scarlett Johansson - Between February and June 2011, the actors were spotted several times, but Penn broke if off, reportedly claiming to not want anything serious.

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Garcelle Beauvais - 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.

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Shannon Costello - 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.

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Calu Rivero - In 2012, Penn was rumored to have dated Argentine actress and model Calu Rivero.

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Charlize Theron - 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.

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Called it off - 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.

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Leila George - 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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Headline-grabbing age gap -

More than two decades exists between George, 27, and Penn, 59. Penn is also just one year younger than her father, and George is one year younger than Penn's daughter Dylan (pictured).

Check out these other celebs with age gaps you wouldn't believe.

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

From Madonna to Charlize, and all the talented women in between

13/08/19 | StarsInsider

CELEBRITY Sean penn

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 with his eccentrically grumpy persona off-screen. 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 dating someone one year younger than his own daughter.

The actor, who turns 59 this year, has cultivated a wild, experimental nature over the years, and yet has proposed to four different women. Click through this gallery to see all the women Penn has romanced, or has been rumored to romance, over the years.