Charlize Theron has been romantically linked to many big names while on her search for The One.

Before making it big in Hollywood, Theron dated actor Craig Bierko in the ‘90s. Following their breakup, the actress moved on with Third Eye Blind’s Stephan Jenkins until 2001. Shortly after, Theron went on to have a serious relationship with Stuart Townsend for nearly a decade. After splitting from Townsend in 2009, Theron wasn’t seriously dating anyone until she began seeing Sean Penn from 2013 to 2015.

While Theron hadn’t found her perfect life partner early on, that didn’t stop her from following her dream to become a mother. She adopted daughters Jackson and August in 2012 and 2015, respectively.

“I haven’t dated anybody for over five years,” she said during a September 2020 appearance on The Drew Barrymore Show. “Once I had my children, it’s not that it replaces something or makes you less interested in [romance] … It’s a lot of work to be a parent and part of that is at the end of the day, I get in bed and I go, ‘Oh, my God, I wouldn’t want this day to be anything different.’”

Theron, for her part, did meet someone who checked off her boxes. Us Weekly confirmed in May 2023 that she was dating Alex Dimitrijevic after meeting at an event a few months before.

Keep scrolling to see Theron’s dating history:

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Craig Bierko

Bierko and Theron began dating in 1995 when she was a rising actress in films like Trial and Error, That Thing You Do! and The Devil’s Advocate.

“I’m the luckiest girl in the world, because Craig is incredibly supportive and makes me feel really safe and protected,” Theron said to the Los Angeles Times in May 1997 before they called it quits later that year.

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Stephan Jenkins

After breaking it off with Bierko, Theron connected with the rockstar while on vacation in Hawaii where Third Eye Blind happened to be performing. The twosome made their debut as a couple at the BMI Pop Awards in May 1998. Two years later, Theron and Jenkins split. In 2003, Jenkins confirmed that his ex inspired some of the songs on Third Eye Blind’s Out of the Vein album.

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Stuart Townsend

Theron and Townsend met while working on the film Trapped in the early 2000s. The actor shared that he was infatuated with Theron after the cast decided to grab 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 told Irish America in 2004. “When she glams up it’s ridiculous. … I was just smitten after that.”

The duo tackled long-distance and lived with one another in both Los Angeles and Ireland. In 2007 things got serious as they were spotted wearing rings and referring to each other as husband and wife, despite not making it legally official. However, Theron and Townsend called it quits in late 2009.

“It was sinking, and I had to give it a fight,” Theron shared with Vogue in November 2011 about her breakup. “I really wanted to try and make it work. That was the priority. I wouldn’t do it any different way.”

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Sean Penn

After being single for several years, Theron began a high-profile relationship with Penn in December 2013. After one year of dating, rumors swirled that the pair got engaged. However, Theron and Penn called it quits in June 2015. Years after their split, Theron clarified she had zero intention to tie the knot with Penn.

“I did not ‘almost get married to Sean’, that’s such bulls–t,” 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.”

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Gabriel Aubry

After her split with Penn, rumors swirled that Theron had moved on with Aubry in 2017. The Oscar winner shut down the speculation during an appearance on Watch What Happens Live With Andy Cohen, and noted that she and Aubry’s children attend the same school. (Aubry shares daughter Nahla with ex Halle Berry.)

However, in May 2022, a source exclusively told Us that Theron and Aubry had connected but it wasn’t serious. “Charlize has been hooking up with Gabriel Aubry,” the insider explained at the time. “They’re very casual and enjoying each other.”

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Alex Dimitrijevic

One year after her romance with Aubry, Us confirmed in May 2023 that Theron and the model had been dating “for a few months” after they met at an event. While the relationship was new at the time, a second source told Us five months later that things were getting serious for the couple — and Dimitrijevic had won over Theron’s friends.

“Charlize’s friends love that unlike some of her other relationships, this one has an ease to it,” the insider shared while noting that the pair were “more in love than ever.” “Friends think they are in this for the long haul.”