Sean Penn's past marriages explored as actor believes he will not have his "heart broken by romance again"

Sean Penn opened up about relationships and heartbreaks (Image via YouTube/Jimmy Kimmel Live)
Sean Penn (Image via YouTube/@Jimmy Kimmel Live)

Mystic River star Sean Penn opened up about not wanting to go through a romantic heartbreak again. In an interview with The New York Times published on Saturday, June 22, the actor revealed that he was "thrilled every day" to be single.

"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, and I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again," he told the publication.

Penn got candid about his experience with romantic relationships. The actor mentioned that he does not love to have "drama in romance" and avoids visits from "the trauma gods."

He has been married and divorced three times in his life. He was first married to Madonna from 1985 to 1989 before he exchanged vows with House of Cards star Robin Wright. After their divorce in 2010, he tied the knot with Australian actress Leila George in 2020 and the duo got divorced two years later.


A glimpse into Sean Penn's marriages and divorces


Sean Penn's well-documented marital life began with his marriage to pop star Madonna in 1985. The singer initially filed for divorce in 1987 before withdrawing the papers 12 days later, as per Today In Madonna History. Four years into their marriage, in 1989, the artist filed for divorce again due to irreconcilable differences.

There were a plethora of reports surrounding their marriage at the time, claiming that Penn had allegedly assaulted Madonna with a baseball bat. However, the allegations were denied by both Penn and Madonna, who according to court documents obtained by People, said:

"I know the allegations in those and other reports to be completely outrageous, malicious, reckless and false."

At a 2016 charity gala in Miami, the Material Girl hitmaker said that she was "still in love" with Penn. In his recent New York Times interview, Penn called Madonna someone he loved and explained:

"It turns out it’s a lot quicker to repair a friendship after divorce if there are not kids involved."

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However, this wasn't the case with Sean Penn's second wife, the Forrest Gump star, Robin Wright. Penn and Wright became parents to a daughter named Dylan in 1991 and a son named Hopper in 1993 before tying the knot in 1996. After spending 14 years together, the couple got divorced in 2010.

In a 2018 appearance on the WTF Podcast, the actor insisted that the former couple "don't not get along". The actor mentioned that the duo did not share the same "ethical views on parenting," Penn said in his interview with The New York Times:

"It took Robin and I quite a while. There was a lot of drama. Much more important to repair it if there are kids involved, but no easy swing, right?"

Penn's third and final marriage was to Australian actress Leila George of Mortal Engines fame. As per People, the couple had an on-and-off relationship since 2016 before tying the knot in 2020. The couple separated a little over a year later in April 2022.

In an April 2022 interview with Hollywood Authentic, Sean Penn claimed that he was still in love with his divorced wife.

"I know that this is my 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," he said.

Sean Penn on never having his heart broken by romance again

While talking to The New York Times in an interview published on Saturday, Sean Penn recalled that the first thing he would see when he woke up were "eyes wondering what I’m going to do to make them happy that day." However, he said this was "rarely reciprocated."

"On one of my marriages, the background noise of life was a 'Housewives of Beverly Hills' or another thing called 'Love Island.' Not even being in the room — I’m not saying this to be cute — I was dying. I felt my heart, my brain shrinking. It was an assault."

As mentioned earlier Penn further spoke about being "free" at the moment and wanting to continue feeling that way, even if he gets into another relationship. The actor said he was "not going to be hurting" and did not think he would have his "heart broken by romance again."

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