Charlize Theron makes rare sex confession and reveals what she regrets not doing in her 20s
Kiesha Dosanjh
Featured Image Credit: YouTube/Call Her Daddy
Charlize Theron is among the long list of celebrities who have spilt all on Alex Cooper’s Call Her Daddy podcast.
Cooper, 31, regularly gets celebrity guests to open up about the intimate details of their lives, and Theron was no different.
Lately, Nikki Glaser went viral after admitting she ‘wouldn’t care’ if her boyfriend Chris Convy were to sleep with other women.
Theron, however, is currently single, and therefore spoke about the intimate and fun details of her life as a 50-year-old, as well as what she regrets not doing in her 20s.
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The Mad Max star has been in a number of high-profile relationships, which included Sean Penn and Stuart Townsend. Theron is now enjoying single life and has regularly expressed that she has no desire to get married.
Lately, the star revealed on The Drew Barrymore Show that she has no interest in living with a partner again, but isn’t opposed to dating, which she also made clear on her NSFW confession on Call Her Daddy.
During the July 2025 episode, the two got onto the topic of one-night stands, in which Theron admitted she had had ‘just three’ in her life. Although it’s something she now regrets and wishes she did more of.
“I don’t have many of them, I’m sitting here sounding like I do,” she said. “So when I do, I’m like ‘oh f**k yeah I should’ve done this in my 20s! I was married from the time that I was like, having sex to the time that I had my last relationship. Then I had children. Who has time for dates, and shaving, and waxing and makeup?”
The star then continued even further as she went into detail about a recent sexual encounter she’d had.
“I did just recently f**k a 26-year-old,” the mother-of-two admitted. “And it was really f*****g amazing.”
“F**k yes!” Cooper cheered as she fist pumped the air in delight.
“I’ve never done that,” Theron continued. “And I was like, ‘Oh this is great!’”
An impressed Cooper then responded: “Can I just say, the 26-year-old is the luckiest man on the planet! He’s walking differently today!”
The Bombshell actress is a mother to adopted daughters, Jackson and August. Theron adopted Jackson in 2012 and August three years later, in 2015.
Opening up about her decision to PEOPLE in 2018, the star said: “Even when I was in relationships, I was always honest with my partners, that adoption was how my family would look one day.
“This was definitely not a second option for me. It was always my first.”
Charlize Theron was first linked to actor Craig Bierko in 1995, as she was starting to make a name for herself in Hollywood
During an interview with The Los Angeles Times in 1997, she admitted: “I'm the luckiest girl in the world because Craig is incredibly supportive and makes me feel really safe and protected.”
They made an appearance at the 1997 Vanity Fair Oscar Party together but ended up splitting later that year.
After calling it quits with Bierko, Theron crossed paths with Third Eye Blind frontman Stephan Jenkins while on vacation in Hawaii.
They first stepped out as a couple at the BMI Pop Awards in May 1998, with many red carpet appearances following.
In October that year, Jenkins told PEOPLE: “She's very funny. And she learned to play the drums faster than anyone I've ever seen.”
Meanwhile, Theron gushed: “He lives for what he does. I found that very attractive. It's nice to be with someone who lives life to the fullest.”
However, the pair ultimately went their separate ways in 2000.
Theron met Irish actor Stuart Townsend while working on the 2001 movie Trapped.
Speaking about Theron when the cast went for dinner, he told Irish America in 2004: “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.
“When she glams up it's ridiculous. … I was just smitten after that.”
In the years that followed, the couple appeared to go from strength to strength. In 2007, they began referring to each other as husband and wife and were even seen wearing rings, despite not being legally married.
However, they broke up in early 2010, with Theron telling Vogue a year later: “It was sinking, and I had to give it a fight.
“I really wanted to try and make it work. That was the priority. I wouldn't do it any different way.”
After being friends for nearly two decades, Sean Penn and Theron’s relationship turned romantic in December 2013.
The high-profile couple attended a whole host of red carpet events together and even collaborated on the 2016 film The Last Face while they were dating.
In early 2015, Penn told Le Parisien: “She's the love of my life.” Theron also called the Mystic River star the ‘love of my life’ in an interview with Elle the same year.
At one point, there were widespread reports that they were engaged, but Theron later clarified that this wasn’t true.
Sadly, it wasn’t to be and the pair split in June 2015.
Theron was romantically linked to model Alex Dimitrijevic in May 2023 after they were spotted out and about together.
While neither party confirmed the nature of their relationship, a source told Us Weekly: “Charlize and Alex have been dating for a few months now.”
It’s not clear how long the reported romance lasted.