What Sean Penn's Relationship With Charlize Theron Was Really Like

After Charlize Theron's long-standing relationship with fellow actor Stuart Townsend ended in 2010, she seemingly took a mini break from finding love. The Oscar winner reportedly got into a relationship with Sean Penn in 2013, with the A-listers first sparking romance rumors after being spotted attending a Halloween party, though they had already known each other for quite some time by then. Speaking to Esquire in 2015, the "Bombshell" star divulged that she met her beau nearly two decades prior and they remained friends throughout their subsequent relationships. 

"I think our friendship stemmed from mutual respect — more on my end, because I really didn't have a body of work twenty years ago, but my love and passion for making films — that was our common ground," she shared. When they were still just friends, Theron found that Penn was a great conversationalist because he wasn't afraid to dive deeper into more serious topics. She was also impressed by how the "Mystic River" star took a more hands-on approach to the world's problems including living in Haiti in 2010 to help the relief efforts following a huge earthquake. 

Since Theron also undertook humanitarian work in her native South Africa, the two quickly bonded over their shared experiences. The daredevil actor, who doesn't shy away from dangerous movie roles, admitted that despite their strong bond, neither party anticipated they would fall in love one day. However, she was ecstatic that things worked out the way they did because it meant Theron and Penn's relationship began on solid ground.

Sean Penn and Charlize Theron's romance started heating up significantly in 2014. The high-profile couple kicked off the year on a high by soaking up the sun on a fun trip to Hawaii. A few days after returning from their holiday, Theron supported Penn at his Help Haiti Home Gala. Later that month, the actors were spotted grocery shopping with her daughter, Jackson Theron, whom the Oscar winner adopted in 2012. The adorable pics showed Penn making silly faces to make Jackson crack a smile while her mom picked out the groceries. 

Throughout their relationship, Jackson and Penn appeared to be super close as the actor often carried the little one around. Eventually, rumors about the "Dead Man Walking" star adopting Jackson started circulating. Charlize dismissed them as false in her 2016 Wall Street Journal interview, asserting, "It's not something that happens in 18 months. You can't do that to a child." As she elaborated Jackson, who was assigned male at birth, was her priority.

Charlize confirmed, "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 was incredibly supportive of her decision to adopt her second daughter, August Theron, in 2015 by herself regardless. Their relationship appeared stronger than ever as Charlize called Penn the "love of my life" during a May chat with Elle after he used the same words to describe her while speaking to Le Parisien in February (via AZ Central).

Sadly, Sean Penn and Charlize Theron couldn't make their love last and called it quits in June 2015, as People reported at the time. A source later claimed to Us Weekly that Theron had ghosted him instead of just being honest about their relationship. The "Atomic Blonde" star denied the rumors while speaking to The Wall Street Journal in 2016. "We were in a relationship and then it didn't work anymore," she clarified of the reason for the split. "And we both decided to separate. That's it." The outspoken star also condemned the media for making mountains out of molehills. 

However, that wasn't the only potentially damaging, and demonstrably false, story that circulated about their romance as many people believed that Penn had popped the question at some point in their relationship. During a 2020 appearance on "The Howard Stern Show," Theron asserted that they'd never moved past the dating stage. "We never moved in. I was never going to marry him. It was nothing like that," she said (via People). Despite their highly publicized breakup, the two don't seem to have any bad blood. 

While speaking with GQ in 2016, Theron revealed that she had caught up with her ex the day before the interview. She explained that people tended to look for the juicy gossip in a celebrity split when, in their case at least, it didn't exist. We witnessed the former couple's brief and awkward reunion at the premiere of "The Last Face" too. Photos from the event showed Theron hugging a stoic and slightly uncomfortable-looking Penn. Ultimately, he married Leila George in 2020 and they divorced in 2022. As for Theron, she never got married — by choice.