Charlize Theron and Sean Penn's romantic relationship looked like it might lead to marriage, especially after they got engaged within 18 months of dating. Sadly things broke down between the pair unexpectedly.
Hollywood superstars Charlize Theron and Sean Penn had known each other for years before becoming romantically involved in 2014. They had been friends for 20 years and even won their first Oscar award the same night back in 2004.
According to the actress, her friendship with Penn stemmed from her respect for him due to his extensive body of work in Hollywood. Penn also liked talking about things other than making movies which was a rare trait among movie makers.
Sean Penn and Charlize Theron at an event [left], Charlize Theron and her child, Jackson with Sean Penn [right] | Photo: Getty Images
It looked like fans would see another megastar Hollywood wedding, but that dream did not come to be. A look into their romantic journey.
CHARLIZE THERON AND SEAN PENN'S SHORT-LIVED ROMANCE.
In 2014, Theron and Penn appeared to have taken a step beyond just friendship when a picture of them celebrating the New Year together in Hawaii surfaced.
Not long afterward, the movie stars confirmed they were in a relationship at the actor's third annual Help Haiti Home gala. Shortly after, the pair became engaged, and Theron showed off her ring while walking through the LAX airport.
The actress declared it was surprising how their friendship turned to love because she was not expecting it. But being in a relationship with Penn made her life better, and people around her saw the actor's effect on her.
It looked like their relationship was progressing when it was revealed that Penn might be taking steps to adopt Theron's adopted child Jackson. The child was also reportedly already calling him "daddy."
Charlize Theron at the premiere of "Atomic Blonde" in July 2017. | Photo: Getty Images
The actress addressed the adoption issue that although Penn was a part of her child's life, becoming the child's daddy would still take a while. She explained:
"There was an understanding that I was a single mom with a very young boy who I had to put in a situation where he understood that Mommy dates, but that he does not have a father."
Penn, who had previously been married to celebrity stars Madonna, and Robin Wright, said he would consider his marriage to Theron as his first one because his previous marriages were not done under his terms.
Madonna and Sean Penn in August 1986 in New York City | Photo: Getty Images
The actor explained that he was a bit naive when he married Madonna and Wright, so he would only consider his next marriage as his first because it would be different this time around.
Penn also disclosed he and his ex-wife Madonna, who he was married to from 1985 till 1989, are still friends; the actor, however, did not disclose much about his relationship with Wright, who was his partner from 1996 till 2010, and he shares two children with, Dylan and Hopper.
The father of two was also looking forward to potentially walking down the aisle with Theron and revealed he was surprised to be in love again.
Robin Wright Penn and Sean Penn arrives at the 15th Annual Screen Actors Guild Awards | Photo: Getty Images
He explained his relationship with the actress might seem too late, but for him to have met someone who he cares about and is very much passionate about is a happier feeling. It is also very romantic and fulfilling to feel good in a relationship.
Sadly the embers of their impending marriage were quenched when after looking very happy together at the Cannes film festival in France, Theron suddenly stopped picking Penn's calls.
REASONS BEHIND THEIR SUDDEN SPLIT
Theron and Penn's sudden split came as a surprise to many, and shortly after it was confirmed, there were reports that the actor's overbearing seriousness was one of the major reasons their relationship broke up.
In an interview with WSJ magazine, Theron disclosed that reports claiming she suddenly ghosted Penn were untrue. She could not understand why people have to make a big deal of a relationship not working out. Theron revealed:
"It's just its own beast. We were in a relationship, and then it didn't work anymore. And we both decided to separate. That's it."
Sean Penn refused to comment on this. The actress also revealed that the news Penn was adopting her child Jackson was false, and taking a step so important was not possible in an 18-month relationship.
She, however, explained that the actor was fine with her arrangements regarding her child and that he was aware she wanted to adopt another child alone before their relationship ended.
Working in the same industry also reportedly created a strain between the pair. Before their split, Penn had directed a movie filmed in South Africa titled "The Last Face," which Theron also starred in.
"Putting aside that he's my partner, he's the love of my life; for the first time, I felt that my work was bleeding into my life, and that made it hard."
She also disclosed that they were both to blame for the way their relationship ended and that there were moments they both were extremely unfair to one another.
MOVING ON FROM THEIR SUDDEN SHORT-LIVED RELATIONSHIP
After her short romantic stint with Penn, Theron declared that she enjoys being single and has not dated anyone since.
The actress explained most of her friends try to set her up with men, and even though she is open to a relationship, she would only accept people who would make her life better and nothing less.
The mother of two, who adopted her second child August after breaking up with Penn, is not lonely because she is focused on raising her kids.
Her children make her less interested in something else because being a parent is a lot of work that requires her undivided attention.
Even though she enjoys being set up on dates, the actress is not sure she would ever live with somebody again. Theron also admitted she may not have all the answers as a white mom parenting two Black kids.
Theron says she is aware of her weaknesses in mothering two Black kids, which is a void she is trying to fill by surrounding herself with strong Black women who sometimes point her in the right direction when parenting her kids.
The actress, who has also been very private about her personal life, revealed her first child Jackson is transgender so that the media would use the right pronouns for her.
On the other hand, Penn married Australian actress Leila George in July 2020 in a quiet ceremony during the COVID lockdown. The pair had known each other since 2016 and had been dating since then before tying the knot.
Sadly, after a year of marriage, the couple separated after George filed for divorce in a Los Angeles County Superior court.