Celebrity4 min(s) read
Published 09:50 08 May 2026 GMT
After Charlize Theron spoke unreservedly about dating younger men and enjoying a new sense of freedom later in life, including a coital exchange with a man 20 years her junior, and she isn't the first celebrity to have entertained younger men...
The term 'cougar' was coined for women who are romantically involved with younger males, with many seeing it as an opportunity to get a new lease of life.
While audiences are used to seeing the revered actress in steamy on-screen roles, she has historically kept her private life out of the spotlight. However, during an appearance on Call Her Daddy with Alex Cooper, Theron spoke openly about sex, dating, and confidence in her 40s.
When Cooper asked her for her best sex advice, Theron joked: “I almost choked. I am the last person to ask.”
The 50-year-old went on to explain how her outlook on relationships has evolved over time. “I'm sounding very cocky here, but I think it's because I found this freedom in my forties, where I'm like, 'Oh my god,'” she said.
Theron then stunned listeners with a candid admission about a recent encounter with a younger man. “I've probably had three one night stands in my entire life, but I did just recently f*** a 26-year-old and it was really f****** amazing and I've never done that and I was like, 'Oh, this is great okay.'”
Cooper responded jokingly: “Let me just say that 26-year-old is the luckiest f****** man walking on this god damn planet.”
Theron laughed off the comment, replying: “He is for sure is not, but thank you.”
The actress, who shares daughters Jackson and August, has largely stayed out of the public dating scene since splitting from Sean Penn in 2015. She also admitted casual relationships are rare for her, adding: “So when I do, I'm like, 'Oh, f*** yeah, I should have done this in my 20s.'”
Jennifer Coolidge previously revealed that her role as “Stifler’s Mom” in American Pie dramatically changed her dating life.
Speaking with Ariana Grande for Entertainment Weekly, Coolidge said: “It helped my dating life in a way that I can't ever explain.”
Reflecting on the attention she received after the movie, she added: “If I hadn't had that movie, I don't think… Well, let's just say it would've been a very dull decade.”
Coolidge also recalled one particularly awkward experience involving a younger partner. “This one guy was particularly young — legal, of course, it was all very legal,” she said. “I won't get into the details. But afterwards, the next morning, I told him I needed to get a blow dry. So he was so young, we called his mother to see where I could get a blow dry.”
Meanwhile, Demi Moore has long faced public attention for dating younger men. Reports recently linked her to Andrew Garfield following their viral interaction at the Golden Globes.
A source claimed: “While Demi isn’t looking to settle down, having someone in her life who she can enjoy some romance with while also connecting on a deeper level would really do her good.”
The insider added: “She and Andrew have a huge physical attraction… Andrew is just her type – he’s tall, fit, and thinks outside of the box.”
Halle Berry has also been linked to younger partners over the years. Commenting on her relationship with music producer Alex da Kid, TV personality Bevy Smith joked: “He’s a younger, tasty gentleman.”
Madonna has also spoken openly about dating younger men and the double standards surrounding it. During an appearance on The Ellen DeGeneres Show, she addressed public fascination with her relationships.
When asked about the youngest man she had dated in recent years, Madonna replied: “The youngest was — in the last six years — 22, yeah.”
Questioning why people are so focused on age gaps, she said: “Why is everyone so obsessed?”
She also pointed out the difference in how society reacts to men dating younger women versus women dating younger men: “Men date younger women all the time and nobody says anything about it. What's wrong with women dating younger men?”
