In the world of Hollywood, age is often just a number, especially when it comes to romantic relationships. A number of prominent female celebrities have opened up about their experiences dating younger partners, challenging societal norms and expectations. From Charlize Theron to Cher, these stars have shared their stories, revealing the joys and complexities of age-gap romances.
Charlize Theron made headlines in June 2025 when she candidly discussed her recent fling with a 26-year-old, describing the experience as “really f*ing amazing.” During an appearance on the “Call Her Daddy” podcast, the Academy Award-winning actress admitted that she had only engaged in a few one-night stands throughout her life but found this particular encounter refreshing. “I’ve probably had three one-night stands in my entire life,” she confessed. “But I did just recently f* a 26-year-old, and it was really f***ing amazing. I was like, ‘Oh, this is great. O.K.’”
Theron’s revelation reflects a growing trend among female celebrities who are unafraid to embrace relationships with younger men. Cher, the iconic singer and actress, has long been an advocate for dating younger partners. Over the years, she has been linked to several younger men, including Tom Cruise and Bon Jovi guitarist Richie Sambora. Cher has openly acknowledged her preference for younger companions, stating, “The reason I got with young men is because men my age or older — well, now they’re all dead — but before, they were always terrified to approach me.”
Another celebrity who has navigated the waters of an age-gap romance is Holland Taylor, who is in a relationship with actress Sarah Paulson, who is 32 years her junior. Taylor has spoken about their partnership, acknowledging the generational differences while also celebrating their shared interests. “We do have a wonderful resonance,” Taylor said. “We are very interested in the same kinds of things, and yet, we share big differences.”
Sonja Morgan, a star of “The Real Housewives of New York City,” has also made headlines for her relationships with younger men. Morgan famously dated real estate developer Benjamin Benallou when she was 49 and he was just 23. At the time, she expressed that she was drawn to him for his elegance and worldly nature, stating, “I don’t care [about being called a cougar]. If you’re a smart guy and you can keep my attention [for] breakfast, lunch, and dinner, that works for me.” However, Morgan later declared that she was done dating younger men, stating in 2016, “I’m always dating, but I’m not dating the young guys [anymore].”
Luann de Lesseps, another “Real Housewives” alum, has also expressed her interest in younger men as she enters her 60s. After two high-profile divorces, she revealed that her ideal partner is “age appropriate” and has an established career. “So, right now, all the 40-year-olds, the 30-40-year-olds, are up into my stuff,” she explained. “But listen, a young 50-year-old … the problem with 50-year-olds is they usually want younger women because they have that ‘midlife crisis.’”
Carole Radziwill, known for her relationship with celebrity chef Adam Kenworthy, also faced scrutiny for dating someone significantly younger. When she began dating Kenworthy, she was 52, and he was just 29. Despite the criticism from her castmates, Radziwill remained unapologetic about her choices, quipping, “Lu lecturing me on dating younger men is like the Saudi government lecturing the world on feminism.” She later shared that dating in your 50s can be liberating, especially when it involves younger partners.
Kristin Cavallari, another Hollywood star who has faced backlash for dating younger men, defended her relationship with 24-year-old Mark Estes when she was 37. In a TikTok video, she addressed the criticism head-on, stating, “When they’re all up in arms that I’m dating a 24-year-old. Andddd?” She emphasized that she wasn’t actively seeking out a younger partner but found happiness with Estes. “This man makes me really happy right now. We’re just trying to have a little fun,” she remarked.
Cher’s romantic history also includes a notable relationship with music executive Alexander “A.E.” Edwards, who is 40 years her junior. Cher explained that her attraction to younger men stems from her experiences with older men, saying, “They were always terrified to approach me.” This sentiment resonates with many women in Hollywood, who find that younger partners are often more open and less intimidated.
Sam Taylor-Johnson, director of “Fifty Shades of Grey,” found love with actor Aaron Taylor-Johnson when she was 42 and he was just 18. The couple has been together for over a decade, and Taylor-Johnson has shared that their age difference has never been an issue in their relationship. “We’re a bit of an anomaly, but it’s that thing: after 14 years, you just think, surely by now it doesn’t really matter?” she stated.
Jada Pinkett Smith’s relationship with singer August Alsina also stirred controversy. The two met when she was 43 and he was 22. Pinkett Smith later clarified that their relationship occurred during a tumultuous time in her marriage to Will Smith, emphasizing that the connection was based on mutual support and healing rather than mere attraction.
Kris Jenner, matriarch of the Kardashian-Jenner clan, has been in a relationship with Corey Gamble, who is 25 years younger than her. Jenner initially questioned why a younger man would be interested in her but eventually learned to embrace their chemistry. “I used to say to Corey all the time when I first started dating him, like, ‘Why do you want to date somebody who is older than you?’” she recalled.
Jennifer Lopez, who has had several high-profile relationships with younger men, including her former backup dancer Casper Smart, has also faced scrutiny for her dating choices. Lopez has addressed the age debate, insisting that it’s not about age but about the connection she feels with her partners. “It’s whether or not I’m attracted to them or not,” she explained. “It has nothing to do with age.”
Demi Moore’s marriage to Ashton Kutcher, who was 15 years her junior, remains one of the most talked-about age-gap relationships in Hollywood. In her memoir, Moore reflected on the challenges posed by their age difference, admitting that she underestimated its significance. “I was a 40-year-old who had a big life, and Ashton’s adult life was just beginning,” she noted.
These stories highlight a growing trend among female celebrities who are redefining what it means to date across age boundaries. They challenge traditional norms and celebrate the happiness and fulfillment that can come from relationships with younger partners. As these stars navigate their personal lives, they remind us that love knows no age and that genuine connections can flourish regardless of the numbers on a birth certificate.