Charlize Theron and More Female Celebs Who Have Opened Up About Dating Younger Partners

Charlize Theron surprised fans in June 2025 by revealing that she recently had a fling with a much younger guy — and found it “really f***ing amazing.”

The Bombshell actress is far from the only female star to speak frankly about age-gap relationships or flings. Cher has proudly acknowledged dating younger men (including Tom Cruise, Bon Jovi guitarist Richie Sambora and Val Kilmer) throughout her life, while Kristin Cavallari insisted she “100 percent didn’t give a s***” about anyone criticizing her romance with a 24-year-old in 2024.

“[My now ex-boyfriend Mark Estes] is 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,” the former The Hills star told podcast listeners.

Keep scrolling for Theron and more female stars opening up about dating younger partners:

Charlize Theron

The Academy Award winner disclosed to Alex Cooper on the “Call Her Daddy” podcast in June 2025 that she’d recently had a one-night stand with a 26-year-old.

“I’ve probably had three one-night stands in my entire life,” Theron, then 49, 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.’”

Theron joked that whenever she does have a one-night stand, she always thinks, “I should have done this in my 20s.”

Holland Taylor

American Horror Story actress Sarah Paulson is 32 years younger than her longtime partner. Taylor told Radio Andy in 2024 that she is conscious of the significant age difference, though their partnership has clearly stood the test of time. (Paulson and Taylor got together in 2015.)

“We do have a wonderful resonance,” Taylor told host Andy Cohen. “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?”

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Taylor identified some ways her and Paulson’s age gap often works to their advantage.

“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,” she said. “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

The Real Housewives of New York City viewers will probably remember that Morgan dated real estate developer Benjamin Benallou when she was 49 and he was 23. Morgan told Enstarz in 2013 that she was dating Benallou because he was “nice [and] very elegant, worldly.”

“I don’t care [about being called a cougar],” she insisted at the time. “If you’re a smart guy and you can keep my attention [for] breakfast, lunch and dinner, that works for me.”

The couple later split, with Morgan promising in 2016 that she was done with younger men.

“I’m always dating, but I’m not dating the young guys [anymore],” Morgan told Life & Style in 2016. “I’m dating serious guys who I think I might have a future with.”

Luann de Lesseps

Morgan’s RHONY costar revealed in 2024 that she was interested in younger men as she entered her 60s. Following high-profile divorces from first husband Alexandre de Lesseps and second husband Tom D’Agostino, she confirmed on Tamron Hall that her ideal guy was “age appropriate” with an established “career.”

As for what she considered “age appropriate,” The Countess clarified: “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.”

“So it’s really from the 40’s…you know, late 30s, 40s, for me, is my sweet spot,” she added. “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

One iconic RHONY storyline involved Radziwill getting involved with celebrity chef Adam Kenworthy, who previously dated Luann’s niece Nicole Nadeau. At the time Carole started seeing Adam, she was 52 and he was 29.

While The Countess may be supportive of age-gap romances these days, she vehemently disapproved of Carole dating Adam, accusing her castmate of dating someone “Sonja young” (as in, seeing someone 25 years younger, just as Morgan did with Benallou.)

Radziwill never paid de Luann’s criticism much attention and memorably quipped on air: “Lu lecturing me on dating younger men is like the Saudi government lecturing the world on feminism.”

Radziwill and Kenworthy split in 2017, though she exclusively told Us Weekly in February 2025 that she still felt dating is “better in your 50s” – especially if you hook up with younger guys.

“I don’t want to say to only date younger guys, but there’s something that [is different],” she joked.

Kristin Cavallari

The former Laguna Beach star is never afraid to clap back and she did just that when some criticised her for dating 24-year-old Mark Estes when she was 37.

“When they’re all up in arms that I’m dating a 24 year old. Andddd?” she wrote via TikTok in March 2024, before sarcastically lip syncing to the audio: “So what are you going to do about it? Are you going to arrest me? Are you going to give me a ticket?”

She subsequently admitted on her “Let’s Be Honest with Kristin Cavallari” podcast in March 2024 that she wasn’t “searching out” a younger guy.

“If you guys listen to the podcast, you know, I thought 30-year-olds were too young for me,” she pointed out. “I understand what it looks like to the outside world, I really do. I get that.”

Cavallari swore that Estes was “not a typical 24-year-old,” before insisting she didn’t “give a f***” about what anyone else thought about her new relationship.

“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 added, “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.”

The pair went their separate ways in September 2024 after seven months of dating.

Cher

The “Believe” singer confirmed in 2022 that she was dating music executive Alexander “A.E.” Edwards, who is 40 years her junior. The pair’s thoroughly modern romance apparently began when they exchanged flirty text messages. Cher clarified on The Jennifer Hudson Show in May 2024 that there was a logical reason why she was drawn to younger men.

“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 has had several other high-profile relationships with younger men, including reportedly dating Tom Cruise and the late Val Kilmer in the 1980s. Cher’s ex-boyfriend Rob Camilletti, then a bagel shop employee, was notoriously dubbed “The Bagel Boy” by the press in the late ‘80s because of their 18-year age difference.

After Cher and Camilletti split in 1989, the Rock and Roll Hall of Fame inductee insisted they were “still best friends” and hit back at the media for obsessing over her ex-boyfriend’s age.

“They were so mean with Robert – you know, ‘the bagel boy,’” she complained to Parade in 2010. “He’s totally worthwhile.”

Sam Taylor-Johnson

The Fifty Shades of Grey director was 42 when she auditioned 18-year-old Aaron to play John Lennon in her movie Nowhere Boy. The pair got together while filming the movie and announced their engagement at the Nowhere Boy premiere in October 2009. They wed in June 2012 and are now parents to two daughters: Wylda, born in 2010, and Romy, born in 2012.

Sam assured The Guardian in 2024 that her and Aaron’s 23-year-old age difference “never does” impact their marriage.

“It comes up on the outside perspective of people who don’t know us, because I guess people will always [judge], ” the filmmaker 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

Singer August Alsina revealed in a 2020 interview that he met Jada, then 43, through his friend — and Pinkett Smith’s son — Jaden Smith when he was 22 and had a short-lived romance with her. The musician claimed that he’d even received her husband, Will Smith’s blessing to date the future Oscar winner’s wife.

The Smiths offered their side of the story on Red Table Talk in July 2020, where Pinkett Smith said she got involved with August during a period where she was “basically broken up” with Will. (Will and Jada later reconciled.)

“It all started with him just needing some help, me wanting to help his health, his mental state,” she said in a discussion with Will. “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.”

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She added, “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.”

During the Smiths’ very frank discussion, Pinkett Smith denied that Will ever gave his blessing for her to date August.

“The only person that can give permission in that circumstance is myself,” she pointed out. “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

A few months after announcing her separation (and eventual divorce) from Caitlyn Jenner in October 2013, Kris started seeing Justin Bieber’s then-tour manager, Corey Gamble. The couple – who have a 25-year age gap – met at designer Riccardo Tisci‘s birthday celebrations in Ibiza in August 2024 and have been together ever since.

On a May 2024 episode of The Kardashians, Jenner remembered initially questioning why a much younger man would be interested in her.

“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 told viewers. “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!”

Jenner admitted that she couldn’t rationalize her and Gamble’s “chemistry” even after a decade together, but she’d learned to simply embrace it.

“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,” she noted.

Jennifer Lopez

The “Jenny From The Block” singer had an on-off relationship with her former backup dancer Casper Smart (who was 18 years younger) between 2011 and 2016. She was later linked to rapper Drake, with whom she had a 17-year age gap.

Appearing on The Ellen DeGeneres Show in 2017, J.Lo seemed exasperated when she was asked why “people make a big deal” about her dating younger guys.

“O.K., first of all, stop,” Lopez playfully told host Ellen DeGeneres. “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 any fixation on the ages of her boyfriends could be perceived as sexist.

“If they’re older, they’re older. If they’re younger, they’re younger,” she insisted. “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

The Substance actress tied the knot with Ashton Kutcher in 2005 when she was 42 and he was 27. They were married for eight years prior to their highly-publicized split in 2013.

Moore later wrote in her 2019 memoir, Inside Out, that she underestimated how significant her and Kutcher’s 15-year age gap would become to their marriage.

“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 explained to Diane Sawyer that her relationship with Kutcher felt like an escape from being “responsible for so much of [her] life.” (She was previously married to musician Freddy Moore from 1981 to 1985 and actor Bruce Willis from 1987 to 2000.)

“All of a sudden, this window opened up where I was safe, I had money, [Ashton] loved my children,” she said.

When Sawyer asked why people were still “shocked” and “unnerved” by her 15-year age difference with Kutcher, Moore replied, “It’s so silly!”