Inside Charlize Theron's Dating History: Stuart Townsend, Sean Penn and More

Charlize Theron has had several notable, high-profile relationships throughout her career.

The Mad Max: Fury Road actress, who is a single mother of two adopted daughters, can name several actors among her exes, including Stuart Townsend and Sean Penn. However, following a series of breakups, she revealed her priorities in love and relationships had shifted.

"I really mean this — people think I joke — I don't think I could ever live with somebody again," she told Drew Barrymore during an April appearance on The Drew Barrymore Show. "I would love for you to be close, like buy the house down the street, but I don't know if I can."

Theron continued, "Maybe it's because I still have my daughters in the house, and maybe that will change when I'm an empty nester, but I'm looking for something very specific."

As the mom-of-two embraces her life as a single mother, OK! takes a closer look at Theron's dating history.

Before making it big in Hollywood, Theron dated actor Craig Bierko in the 1990s.

"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 May 1997.

However, their romance eventually fizzled out, and they split in 1998.

The Prometheus star moved on with Third Eye Blind frontman Stephan Jenkins after meeting him in Hawaii in 1997. They made their red carpet debut at the BMI Pop Awards in 1998 and continued making public appearances together in the months thereafter.

Jenkins spoke fondly about his then-girlfriend in an interview with People, sharing, "She's very funny. And she learned to play the drums faster than anyone I've ever seen."

Theron then said, "He lives for what he does. I found that very attractive. It's nice to be with someone who lives life to the fullest."

They called it quits after about two years of dating.

Theron and Townsend met during a read-through for Trapped in the early 2000s. In a 2004 interview with Irish America, Townsend revealed he initially "did not take that much of notice" but became interested in her when the cast grabbed dinner.

"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 said of Theron. "When she glams up it's ridiculous. … I was just smitten after that."

They fueled marriage rumors in 2007. At the time, Townsend confirmed he was "married" but not legally.

"I didn't do a church wedding or anything, but we're married. We're husband and wife," he continued. "We love each other and we want to spend our lives together."

They also discussed the possibility of having children, with Theron declaring Townsend would be their "baby's father."

But their relationship lost momentum in early 2010, and the two went separate ways.

"It was sinking, and I had to give it a fight," Theron told Vogue about the "devastating" split. "I really wanted to try and make it work. That was the priority. I wouldn't do it any different way."

In 2013, Theron found love again and began dating Penn.

"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 an April 2015 interview, "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."

They fueled engagement rumors in April 2015, though the buzz died down after they made their last red carpet appearance as a couple at the Cannes Film Festival in May of that year.

Theron and Penn officially called it quits in June 2015.

"I did not 'almost get married to Sean', that's such bulls---," she explained to 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."

The Monster actress fueled dating speculation with Gabriel Aubry in 2017, though she shut down the claims during an appearance on Watch What Happens Live With Andy Cohen.

Romance rumors began circulating again in May 2022. A Us Weekly source said Theron had been hooking up with Aubry, though the buzz died down again afterward.

Theron was also romantically linked to Alexander Skarsgård in 2017 after they worked together on the film Long Shot. Neither of them ever publicly confirmed the relationship.

Theron's most recent relationship was with model Alex Dimitrijevic.

In May 2023, Us Weekly reported they had been dating "for a few months" after meeting at an event. Five months later, a second source revealed things were getting serious, with Theron's friends reportedly approving of the romance.

"Friends think they are in this for the long haul," said the insider.

They reportedly broke up in November 2024.

Following the split, Theron confirmed she had joined the popular dating app Raya and "went on two dates."