In June 2025, Charlize Theron surprised fans by sharing that she recently had an intimate encounter with a significantly younger man, describing the experience as incredibly thrilling. This candid revelation fits into a wider trend of prominent female celebrities openly discussing the unique joys and challenges of dating younger partners.
Several renowned women, including Cher, Kristin Cavallari, and others, have embraced relationships with younger men, often addressing public scrutiny with frankness and confidence. From Hollywood stars to reality TV figures, these women highlight why age gaps in romance can offer fresh and fulfilling experiences.
Charlize Theron Opens Up About Her Surprising One-Night Stand
The Oscar-winning actress spoke candidly on the Call Her Daddy podcast in June 2025, revealing a previously private detail of her dating life. Theron, at 49 years old, admitted to having a one-night stand with a 26-year-old, an experience she described with enthusiasm and astonishment.
I’ve probably had three one-night stands in my entire life,
Theron confessed.
But I did just recently f*** a 26-year-old and it was really f***ing amazing. And I’ve never done that. I was like, ‘Oh, this is great. O.K.’
She recalled how the encounter made her wonder if she should have explored such experiences earlier in life, adding with humor,
I should have done this in my 20s.
Holland Taylor Reflects on a Relationship With a Significant Age Difference
Acclaimed actress Holland Taylor, known for her work in American Horror Story, has been with Sarah Paulson since 2015 despite their 32-year age gap. On a 2024 Radio Andy interview, Taylor discussed the distinct challenges and advantages of their partnership, acknowledging both shared interests and generational differences.
We do have a wonderful resonance,
Taylor said.
We are very interested in the same kinds of things, and yet, we share big differences. We have a big generational difference between us, which worries me for her sake, but what can I do?
She elaborated on how Paulson’s current emotional experiences often remind her of similar moments from decades prior, allowing deeper empathy.
A lot of the things that she’s going through, that are very emotionally important to her right now, I went through 40 years ago, 30 years ago,
Taylor added.
She brings [these things] up in my memory, and I think, ‘Oh, of course this is hard!’ Or, ‘Of course, that’s great! Of course, that’s important to her!’
Sonja Morgan’s Experience with Dating Much Younger Men
Sonja Morgan, a familiar face to The Real Housewives of New York City fans, previously dated real estate developer Benjamin Benallou when she was 49 and he was 23. In a 2013 interview, she described her attraction to Benallou as stemming from his charm and worldly demeanor.
I don’t care [about being called a cougar],
Morgan asserted.
If you’re a smart guy and you can keep my attention [for] breakfast, lunch and dinner, that works for me.
Although she later declared she was done dating younger men, opting instead for relationships with more mature partners, Morgan’s earlier experience illustrates how such relationships can be based on genuine connection rather than age.
I’m always dating, but I’m not dating the young guys [anymore],
she shared in 2016.
I’m dating serious guys who I think I might have a future with.
Luann de Lesseps Discusses Her Preferences in Younger Romances
Luann de Lesseps, another RHONY alumna, openly expressed in 2024 her evolving perspective on dating as she moved into her 60s. Having divorced twice, she talked about her attraction to men she called “age appropriate,” typically in their late 30s to 40s with established careers.
Age appropriate for me is … well I’ll tell you something: so, right now, all the 40-year-olds, the 30-40-year-olds, are up into my stuff, if I can say that. The 50-year-olds are like, ‘Oh damn, I’m 50. I need a 20-year-old.’ The 60-year-olds are a little challenged, you know what I mean, down in that department. And the 70-year-olds just want to have a good time all day long,
she explained.
The Countess highlighted that for her, men in their late 30s through 40s were ideal, although she noted some younger 50-year-olds could also be appealing. She criticized men in their 50s who pursue much younger women due to what she described as “midlife crises.”
So it’s really from the 40’s…you know, late 30s, 40s, for me, is my sweet spot,
de Lesseps said.
But listen, a young 50-year-old … but the problem with 50-year-olds is they usually want younger women because they have that ‘midlife crisis.’
Carole Radziwill and Her 29-Year-Old Partner
Carole Radziwill, another RHONY personality, was involved with celebrity chef Adam Kenworthy, who was 29 while she was 52. While her castmate Luann de Lesseps expressed disapproval at the age gap, Radziwill dismissed the criticism and even joked on air about Luann’s comments.
Lu lecturing me on dating younger men is like the Saudi government lecturing the world on feminism.
Although Radziwill and Kenworthy ended their relationship in 2017, she later told Us Weekly in 2025 that she found dating in her 50s to be better in some ways, especially when younger partners are involved.
I don’t want to say to only date younger guys, but there’s something that [is different],
she joked.
Kristin Cavallari’s Bold Defense of Her Relationship With a Younger Man
Kristin Cavallari openly confronted criticism after dating 24-year-old Mark Estes when she was 37. On TikTok in March 2024, she defiantly challenged her detractors.
When they’re all up in arms that I’m dating a 24 year old. Andddd?
She followed the statement with a sarcastic lip-sync:
So what are you going to do about it? Are you going to arrest me? Are you going to give me a ticket?
On her podcast, Cavallari clarified she was not actively seeking a younger partner and emphasized that Estes was not a typical 24-year-old. She insisted she did not care about others’ opinions.
My entire career has prepped me for this moment because when this news came out, it’s the first time in my entire life I 100% haven’t given a s*** what anybody thinks,
she said.
She described her relationship as serious and meaningful despite its relatively short duration, with the couple separating after seven months.
He’s in a place where he’s ready for a relationship and so here we f***ing are. This man makes me really happy right now. We’re just trying to have a little fun. Well, I mean, no it’s — it’s more than that. I don’t wanna downplay it, because I really do like this guy and I actually think what we have is very serious.
Cher Explains Why Younger Men Appeal to Her
Cher, a legendary singer and actress, confirmed in 2022 her relationship with Alexander A.E. Edwards, who is 40 years younger. Their romance reportedly began through flirty texting, demonstrating a modern connection that defies traditional norms.
On The Jennifer Hudson Show in 2024, Cher provided insight into her preference for younger men, explaining her reasons with candor.
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,
she said.
And younger men — they were raised by women like me.
Cher’s history of relationships with younger men dates back decades, including rumored romances with Tom Cruise and Val Kilmer in the 1980s. Her ex-boyfriend Rob Camilletti, known as “The Bagel Boy,” brought considerable media attention due to their 18-year age gap.
They were so mean with Robert – you know, ‘the bagel boy,’
Cher lamented in 2010.
He’s totally worthwhile.
Director Sam Taylor-Johnson on Managing an Age Gap Marriage
Sam Taylor-Johnson, director of Fifty Shades of Grey, married actor Aaron Taylor-Johnson, who was 18 years her junior, after meeting during the filming of Nowhere Boy. The couple married in 2012 and share two daughters.
In a 2024 interview with The Guardian, Sam addressed public curiosity about their age difference, emphasizing its non-impact on their strong marriage.
It comes up on the outside perspective of people who don’t know us, because I guess people will always [judge],
she said.
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?
Jada Pinkett Smith Shares the Context Behind Her Relationship With August Alsina
In 2020, singer August Alsina revealed a brief romantic relationship with Jada Pinkett Smith, who was 43 at the time while Alsina was 22. The relationship received significant media attention due to this age difference and the involvement of Jada’s husband, Will Smith.
Pinkett Smith clarified on Red Table Talk that the relationship occurred during a phase when she and Will were separated, but emphatically denied any suggestion that Will gave his blessing.
It all started with him just needing some help, me wanting to help his health, his mental state,
Jada said.
The outpouring for him from our family was initially about his health. We found all those different resources to help pull him through and, from there, [Will] and I were going through a very difficult time.
She discussed her own emotional pain and the healing role this relationship played during a vulnerable period.
I was in a lot of pain, and I was very broken. In the process of that relationship, I definitely realized that you can’t find happiness outside yourself. I just wanted to feel good, it had been so long since I felt good … and it was really a joy to just help heal somebody.
She added,
The only person that can give permission in that circumstance is myself,
and explained,
But what August was probably trying to communicate because I could see how he could see it as permission because we were separated amicably, and I think he wanted to make it clear he’s not a home-wrecker because he’s not.
Kris Jenner on Embracing an Age Gap Relationship With Corey Gamble
Following her separation from Caitlyn Jenner, Kris Jenner began dating Corey Gamble, who is 25 years younger, after meeting at a birthday party in Ibiza in August 2024. The couple have remained together for nearly a decade.
Jenner reflected in a 2024 episode of The Kardashians on her initial surprise at her younger partner’s interest but ultimately learned to accept age as a number.
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.
I didn’t get the age gap, and then he taught me that age is just a number. It’s a f***ing big number, but it’s a number!
She admitted she cannot quite explain their chemistry but described their relationship as joyous and filled with fun.
Listen, I can’t explain someone’s chemistry or why people fall in love but it’s been an amazing almost 10 years, and we have a great time,
Jenner stated.
Jennifer Lopez Responds to Criticism About Dating Younger Men
Jennifer Lopez, known for her music and acting career, previously dated backup dancer Casper Smart, who was 18 years her junior, and rapper Drake, with whom she has a 17-year age difference. During a 2017 appearance on The Ellen DeGeneres Show, Lopez expressed frustration with societal double standards regarding her relationships.
She dismissed age as an important factor in who she chooses to date, emphasizing personal connection over numbers.
It’s not like you have to be younger, it’s not about that. I just meet people, and if I go out with them, I go out with them, and if I like them, I like them, and if I don‘t, I don’t. It’s just about the person. It’s about who they are. It has nothing to do with age.
Lopez suggested that scrutiny over her partners’ ages might reveal sexist attitudes.
If they’re older, they’re older. If they’re younger, they’re younger,
she said,
It doesn’t matter. It’s whether or not I’m attracted to them or not, attracted to their spirit, their soul, whatever their energy is.
Demi Moore Reflects on Her Marriage to Ashton Kutcher
Demi Moore married Ashton Kutcher in 2005 when she was 42 and he was 27, and they divorced in 2013 after eight years. In her 2019 memoir, Inside Out, Moore revealed that she had underestimated the impact of their 15-year age gap on their relationship.
I was a 40-year-old who had a big life and Ashton’s adult life was just beginning,
she recalled.
I didn’t see all that because I was inside of it. I just felt like a 15-year-old girl hoping that somebody liked me.
Moore later told Diane Sawyer that her relationship with Kutcher offered a break from heavy responsibilities and provided a place of safety and love for her children.
All of a sudden, this window opened up where I was safe, I had money, [Ashton] loved my children,
she said.
Regarding public reactions to their age difference, Moore called the shock “silly.”
The Cultural Shift: Why These Age-Gap Relationships Matter
The details shared by Charlize Theron and these other celebrities illustrate a growing openness toward diverse types of relationships, especially those that challenge conventional age norms. Their stories reveal experiences that range from joyful connections and deep compatibility to public scrutiny and personal growth.
By openly discussing their relationships with younger partners, these women contribute to shifting the cultural conversation, encouraging acceptance and understanding that successful partnerships can come in many forms. The trend may inspire further dialogue about love, age, and societal expectations moving forward.
Our Reader’s Queries
Q. What illness did Charlize Theron have as a child?
A. Theron went to Putfontein Primary School but felt she didn’t fit in there. During her childhood, she often suffered from jaundice. The antibiotics she took caused her upper baby teeth to decay, and they needed to be surgically extracted.
Q. Does Charlize Theron have OCD?
A. In a radio interview, Oscar-winning actress Charlize Theron talked about her past struggles with OCD. She mentioned having obsessive thoughts, such as needing items arranged in a particular order. She also experiences difficulty sleeping when she worries about things being out of place at home.
