Sean Penn is as well known for his high-profile romances and marriages as he is for his acting prowess.
The two-time Academy Award Best Actor winner turned director has been married three times and had a string of high-profile romances with some of the world’s most famous women.
Now back on good terms with at least two of his three ex-wives, Sean Penn is reportedly ‘thrilled’ to be single and revealed he still loves first wife Madonna.
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Elizabeth McGovern
It was on the set of Racing The Moon in 1984 where Penn met and fell in love with his co-star Elizabeth McGovern.
He proposed to McGovern when he was just 23.
McGovern, who went on to have a stellar career and starred in hit films and TV shows including Downton Abbey, later described their relationship as “so exhausting” in an interview with the Daily Mail.
“In the beginning, it was fun. We were a similar age and in the same place professionally, so we were experiencing everything together,” she said.
“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.”
Madonna
After the two broke up, Penn went headlong into a relationship with Madonna, whom he met on the set of her musical video for hit Material Girl.
The music video’s director was a friend of Penn’s and asked if he wanted to come along and watch.
In the 2008 book Life With My Sister Madonna, Christopher Ciccone said Madonna was sashaying down a staircase, decked out as Marilyn Monroe, when she spotted the actor.
“He is 24, she is 26, their birthdays are just one day apart, and – for both of them – it is love at first sight,” he wrote.
They married months later, on August 16, 1985. It was Madonna’s 27th birthday while Penn turned 25 the next day.
But the marriage was short-lived. As her star rose dramatically, Penn reportedly could not cope with the media intrusion and had more than one violent confrontation with the press.
Madonna filed for divorce in December 1987, after two years of marriage, but had a change of heart two weeks later.
However, in January 1989, she filed for divorce again. This time it was over.
But the couple seemingly put the past behind them, reuniting publicly several times over the years.
Now, 35 years after their divorce, Penn spoke of Madonna just this week during an interview with The New York Times, saying “She’s someone I love.”
Robin Wright
Penn moved on quickly after his marriage to Madonna and reportedly began dating actress Robin Wright in 1989.
The couple welcomed daughter Dylan in April 1991, followed by son Hopper in August 1993 before separating for the first time in 1995.
During their split, Penn started a relationship with singer Jewel, who was 20 at the time.
Penn and Wright later reconciled and married in April 1996. They remained together for a decade before filing for divorce in December 2007. They reconciled a few months later, only to separate again in April 2009. They reconciled and separated again before their divorce was finalised in July 2010.
Penn admits things were not good between the pair for some time. “It took Robin and I quite a while. There was a lot of drama,” he said.
But now they are friends again and even had to hose down romance rumours when they were seen out together in 2023.
Charlize Theron
Penn started dating South African born actress Charlize Theron in December 2013.
Theron told Esquire the two first met decades before and were friends during their previous relationships before they started dating.
The couple were regularly seen on the red carpet and out and about, including with Theron’s first child Jackson, whom she adopted in 2012. They even called each other the loves of their lives in separate interviews.
But it did not last, with the pair breaking up in June 2015.
While there were reports they were engaged and living together during their relationship, Theron later said this was not the case. She also denied she ‘ghosted’ Penn at the end of their relationship.
She told The Wall Street Journal in 2016, “We were in a relationship and then it didn’t work anymore,” she said.
Leila George
In 2016, Penn started dating Australian-born actress Leila George, daughter of actors Greta Scacchi and Vincent D’Onofrio,
After an on-off relationship, the two married on July 30, 2020.
But just over a year later, George filed for divorce and their split was finalised in April 2022.
Olga Korotyayeva and Nathalie Kelley
In May 2023, Penn was spotted dining with Ukrainian born actress Olga Korotyayeva.
Penn later confirmed the relationship during an interview with Piers Morgan.
However, the relationship was short-lived and by December last year he was reportedly dating Australian-raised Nathalie Kelley.
Single life
Penn, 63, is now reportedly single and is thrilled, judging by his recent comments to The New York Times.
“I’m just free,” he told the media outlet. “If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it.
“I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.”
He said he planned to avoid “unnecessary drama” in future relationships and would not miss the pressure to make someone happy every day when it was “rarely reciprocated.”