Charlize Theron's Dating History: From Stuart Townsend to Sean Penn

After splitting with Sean Penn in 2015, Charlize Theron was briefly rumored to be seeing Alexander Skarsgård

Charlize Theron has high standards when it comes to her dating life.

The Atomic Blonde actress has had several high-profile relationships with actors like Sean Penn and Stuart Townsend. Since becoming a mom to daughters Jackson and August, however, Theron's priority has been raising her two girls.

"Once I had my children, it's not that it replaces something, or that it makes you less interested in something else," she said on The Drew Barrymore Show in 2020. "I'm still firing on all cylinders. I just think your priorities are in a place that is of high demand; it's a lot of work to be a parent. Part of that is at the end of the day I get to bed and I think, 'Oh my God, I wouldn't want this day to be any different.' "

Although she hasn't seriously dated anyone in several years, Theron has said she's not lonely — and she hasn't been short on romantic prospects, either. In 2017, she alluded to a secret date with a "famous" mystery man, and during the COVID-19 pandemic, "somebody was interested in doing this thing with" her — but she ultimately turned them down.

"It was just a deep dive into a relationship," she told Harper's Bazaar in September 2022. "And I was just like, I don't know if I wanna. … I just feel so out of practice."

The South African star also told Barrymore that she was "open" to new relationships, but any man looking to date her has to "come with a lot of game."

"Not the kind of game that we think of. The kind of game that's like, 'My life is really good, so you better be able to bring that and maybe better,' because I just won't accept anything less," she explained.

Here's a look back at Charlize Theron's dating history.

Craig Bierko

Before Theron made it big in Hollywood, she dated actor Craig Bierko in the '90s. Although not much is known about their relationship, the couple reportedly began dating in 1996.

"I'm the luckiest girl in the world because Craig is incredibly supportive and makes me feel really safe and protected," she told the Los Angeles Times in 1997.

They stepped out together at the 1997 Vanity Fair Oscar Party before going their separate ways in 1998.

Stephan Jenkins

Following her split from Bierko, Theron met Third Eye Blind frontman Stephan Jenkins in late 1997. The pair first crossed paths while Theron was vacationing in Hawaii, where Third Eye Blind happened to be playing a show. They connected after the concert and soon began dating.

Although they initially kept their romance under wraps, they made their first public appearance at the BMI Pop Awards in May 1998 and went on to appear on numerous red carpets together. During their relationship, Jenkins split time between San Francisco and L.A., where he lived off and on with Theron, according to SFGate.

In October 1998, they briefly commented on their relationship with PEOPLE.

"She's very funny. And she learned to play the drums faster than anyone I've ever seen," Jenkins said. Theron added: "He lives for what he does. I found that very attractive. It's nice to be with someone who lives life to the fullest."

Throughout the rest of their relationship, however, the couple kept it private and refrained from speaking about each other.

By the fall of 2000, rumors surfaced that their relationship was on the rocks, and just a few months later, they went their separate ways. Following the release of Third Eye Blind's album Out of the Vein, Jenkins confirmed to Entertainment Weekly that Theron was an inspiration for some of the songs.

Stuart Townsend

When Theron joined the cast of Trapped in the early 2000s, she connected with Irish actor Stuart Townsend. The pair met during an initial read-through, but Townsend recalled that he "didn't take that much notice" of her because they were working. However, that quickly changed at a dinner with the cast.

"She just looked like a million dollars. I went, 'Whoa! Who is this girl?' It was funny because I guess there had been so much going on at the reading I hadn't really taken stock of her," he told Irish America in 2004. "When she glams up it's ridiculous. … I was just smitten after that."

In 2005, Theron recalled to Marie Claire that she wasn't sure Townsend met the "criteria" for "anything serious," considering they lived in different countries. But they couldn't deny that there was a spark between them. They began going on dates anyway and wound up falling for each other.

The couple kept their relationship low-key until mid-2001, when they were seen at a Bob Dylan concert in Ireland, per ABC. Later that month, they were spotted showing PDA during a trip to L.A. In August, they made their first public appearance at a press event for The Curse of the Jade Scorpion.

By 2004, things had gotten pretty serious between the two — Theron told ABC that dating Townsend was like winning the lottery. They also lived together in L.A. and costarred in another film, Head in the Clouds. Amid rumors that they were going to tie the knot, Theron clarified that they weren't looking to marry.

"It's not really what I want, or what he wants. But that doesn't mean I don't want to spend the rest of my life with him. I really don't need to wear a white dress and throw a big party. That, to me, is like a premiere," Theron told Marie Claire.

However, in 2007, the couple had started calling each other husband and wife and were seen wearing commitment rings — despite not legally getting married. That year, Theron appeared in Townsend's directorial debut, Battle in Seattle.

Seven years in, they had even discussed welcoming children; Theron said she was completely sure she was "going to be a mother" one day. "Stuart will be our baby's father. That's something I'm sure of," she told Elle UK in 2008.

Theron and Townsend didn't make it to parenthood together, though, as their relationship eventually hit the rocks. Theron later told PEOPLE she even took a step back from acting in order to work on their relationship and attend couple's therapy. After almost 10 years together, the two actors called it quits in early 2010. Theron has since recalled that their split was "devastating."

"It was sinking, and I had to give it a fight," she shared with Vogue in November 2011. "I really wanted to try and make it work. That was the priority. I wouldn't do it any different way."

Sean Penn

By the time Theron began dating the Fast Times at Ridgemont High star in 2013, the pair had already been friends for almost two decades. They had both been in other relationships but remained in each other's lives thanks to a shared passion for film and charity work.

"I think our friendship stemmed from mutual respect — more on my end, because I really didn't have a body of work 20 years ago, but my love and passion for making films — that was our common ground," Theron told Esquire in April 2015, "and also, Sean liked to have conversations outside of just making movies. That's sometimes hard to find among friends here, and that's where our friendship really blossomed."

While the couple kept the early days of their relationship private, they first sparked dating rumors when they were seen looking cozy at a Halloween party in 2013. They were later spotted together in Hawaii, where they rang in 2014 at Penn's beachfront home. Later in January, Theron attended Penn's annual Help Haiti Home Gala, where the duo reportedly sat side-by-side all night. Not long after, Penn began spending time with Theron's daughter Jackson, whom she adopted in 2012.

By April 2015, there were already rumors of an engagement, but Theron was quick to shut down the idea of getting married. Although she wasn't about to walk down the aisle with Penn, she had nothing but great things to say about their relationship.

"The moment that we're in is just really good. It's really good, really nice," Theron told Esquire. "The marriage thing is always so strange to me anyway. I love the possibility of anything, but I'm really enjoying myself and the everyday moment."

Theron and Penn continued to date through 2014, attending numerous red carpets together and filming The Last Face in South Africa. Things proved to be getting serious between them in early 2015 — Penn told Le Parisien, "She's the love of my life." The feeling appeared to be mutual, with Theron telling Elle UK, "He's my partner, he's the love of my life."

Despite Theron and Penn's love for each other, their relationship wasn't meant to last. They made their last red carpet appearance as a couple at the Cannes Film Festival. In June 2015, it was confirmed that they had split. Following their breakup, rumors surfaced that Theron had ghosted Penn — which she later said was not true.

"There is this need to sensationalize things," Theron explained. "When you leave a relationship there has to be some f—ing crazy story or some crazy drama. And the f—ing ghosting thing, like literally I still don't even know what it is. … We were in a relationship and then it didn't work anymore. And we both decided to separate. That's it."

Theron and Penn reunited for reshoots of The Last Face and for promotional events for the film shortly after their split. The pair seemed to avoid each other for the most part, aside from the 2016 Cannes Film Festival, in which they shared a hug and kiss on the cheek.

Looking back on the relationship years later, Theron addressed the seriousness of the romance, sharing that there was never any truth to their engagement rumors.

"That's not true. No. I did not 'almost get married to Sean', that's such bulls—," she told Howard Stern in 2020. "No, we dated, that was literally all we did, we dated. It was a relationship, for sure. We were definitely exclusive, but it was for barely a year."

Alexander Skarsgård

In late 2017, Theron worked with Alexander Skarsgård on the film Long Shot (originally titled Flarsky). In the months that followed, the pair were rumored to be dating. Though they never confirmed their relationship, when Skarsgård was asked about their romance in September 2018 by WSJ. Magazine, he didn't exactly deny that something had gone on between them.

"It doesn't affect me. People can think whatever they want," Skarsgård told the outlet of the rumors. "It's impossible to live in a vacuum — you hear, 'Oh, I heard you're dating so-and-so.' Sometimes you're like, 'Yeah, I did.' Sometimes it's, 'Never met the person but give her my number.' "

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