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Famous Women Who Dated Younger Men: Olivia Wilde, Kourtney Kardashian, & More

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Famous Women Who Dated Younger Men: Olivia Wilde, Kourtney Kardashian, & More


There’s nothing holding these famous women back from going after what they want! From Olivia Wilde to Helena Bonham Carter, check out the famous ladies who dated younger men!

Don’t call them cougars, call these women who’ve dated younger men exactly what they are: heroes! Celebrities like Jennifer Lopez, 51, and Mariah Carey, 50, have known for years what so many women are figuring out now — that there’s no need to limit yourself to just one age range. Women have every right to pursue someone young and hot, like men have been for centuries! And these women have totally recognized that at some point in their love lives:

Olivia Wilde, 36, & Harry Styles, 26

Olivia Wilde and Harry Styles were seen holding hands while attending a friend’s wedding in January 2021 (AP)

Olivia Wilde started 2021 on the right foot – or, in this case, on the right hand. The Booksmart director/celebrated actress was spotted holding hands with Harry Styles at his agent’s wedding in San Ysidro Ranch in Montecito, California. Olivia – who is ten years older than the “Watermelon Sugar” singer – recently worked with Harry on the film Don’t Worry Darling. This PDA came weeks after news broke that Olivia and her longtime partner, Jason Sudeikis, had split in early 2020. As for Olivia and Harry, PEOPLE reported that they’ve been dating “for weeks.”

Kourtney Kardashian, 41, & Younes Bendjima, 27

Kourtney Kardashian
Kourtney Kardashian and Younes Bendjima dated for a few years [SplashNews].

Kourtney Kardashian can get it! After being with Scott Disick, 37, for nine years, she was linked to a few younger men. She was rumored to be hooking up with Justin Bieber, 26, for some time, and while that romance remains unconfirmed, Kourt did have a relationship with French model Younes Bendjima! Their chemistry was on fire during their romance, but apparently the age difference was causing them problems. The two went their separate ways after the 2019 holidays.

Helena Bonham Carter, 54, & Rye Dag Holmboe, 32

Helena Bonham Carter and Rye Dag Holmboe
Actress Helena Bonham Carter and boyfrind Rye Dag Holmboe take their dogs for a walk in London in Nov. 2020. Photo credit: NASH / BACKGRID.

On Netflix’s The Crown, Helena Bonham Carter‘s Princess Margaret found love with landscaper Roddy Llewellyn, who was 17 years her junior. In real life, the 54-year-old actress has been happily dating psychoanalyst Rye Dag Holmboe, 32, after meeting by chance at a 2018 wedding. “He’s magic, and that’s all I’m going to say,” the British thespian told UK’s The Guardian in 2020 of her 22-years-younger boyfriend. “I met him at a wedding. A totally random thing, which both of us nearly didn’t go to, so it was one of those moments that was so chance and ended up determining so much. A really happy accident, and it’s an amazing thing.” Helena previously was involved in a 13-year relationship with director Tim Burton, 62.

Kate Beckinsale, 47, & Goody Grace, 23

Kate Beckinsale, Goody Grace
Kate Beckinsale and Goody Grace split in October 2020 [P&P / MEGA].

Kate Beckinsale and Goody Grace were such a cute couple. The pair started dating in 2020 during Los Angeles lockdown amid the coronavirus pandemic. While they were seen out and about, at times, the pair were very private and rarely shared social media posts featuring each other. Sadly, the two just split, with Kate deleting the couple’s pics on her Instagram page. Kate has previously dated younger men like Pete Davidson, 26, too!

Demi Moore, 57, & Ashton Kutcher, 42 

Demi Moore, Ashton Kutcher
Demi Moore and Ashton Kutcher split in 2013 [AP Images].

At one point, Demi More and Ashton Kutcher were THE hot Hollywood couple, and yes, their relationship was considered scandalous. This wasn’t a fling with some boy toy; Demi and Ashton were married for eight years, and he was a doting stepfather to her kids — even if Rumer Willis was only 10 years younger than him! Their relationship, sadly, unraveled and in 2013 they divorced. Demi opened up about her marriage to Ashton in her memoir, Inside Out.

Mariah Carey, 50, & Nick Cannon, 40 

Mariah Carey, Nick Cannon
Mariah Carey and Nick Cannon were married for eight years [NIVIERE/SIPA].

Mariah Carey had an epic love story with Nick Cannon. Somehow, one of the biggest pop divas married and had kids with a former Nickelodeon star and the host of Wild N’ Out. Weird, right? Opposites attract, until they don’t; Mariah and Nick officially divorced in 2016 after a long period of separation.

Madonna, 62, & Guy Ritchie, 52 

Madonna, Guy Ritchie
Madonna and Guy Ritchie were married for eight years [AP Images].

She’s the Queen of Pop; she can get with any person in the world! At one point in time, Madonna was married to prolific English director Guy Ritchie, who’s responsible for films like Snatch and Sherlock Holmes. Madonna’s 10 years older than her ex-husband, to whom she was married for eight years. They have two sons together, Rocco and David Ritchie.

Jennifer Aniston, 51, & John Mayer, 43 

Jennifer Aniston, John Mayer
Jennifer Aniston and John Mayer dated for roughly one year [AP Images].

Another unlikely pairing! Jennifer Aniston mixed genres and dated “Daughters” singer John Mayer for about a year. Their relationship was short-lived, but apparently made a lasting impression on John. Jennifer’s on the list of exes he insulted in a 2010 Rolling Stone interview.

Gabrielle Union, 47, & Dwyane Wade, 38 

Gabrielle Union, Dwyane Wade
Gabrielle Union and Dwyane Wade are happily married [SplashNews].

A happy example on this list! Gabrielle Union and Dwyane Wade got married in 2014 after dating since 2009, and they’re hopelessly in love. The couple welcomed their baby girl, Kaavia, via surrogate in 2018. And the two simply gush about one another on social media!

Halle Berry, 54, & Gabriel Aubry, 44 

Halle Berry, Gabriel Aubry
Halle Berry and Gabriel Aubry were together for five years [AP Images].

Halle Berry has absolutely no problem dating younger men. One of Halle’s former partners, model Gabriel Aubry, is 10 years her junior. She was in a relationship with the incredibly handsome French Canadian model for five years, and he is the father of her daughter, Nahla Aubry. That relationship went sour, but it was sweet while it lasted.

Cameron Diaz, 48, & Benji Madden, 41 

Cameron Diaz, Benji Madden
Cameron Diaz and Benji Madden announced that they welcomed their first daughter in early 2020 [SplashNews].

Fifteen years ago, would hearing that the guy from Good Charlotte was married to one of the stars of Charlie’s Angels make any sense to you? Hey, the heart wants what it wants! Cameron Diaz and Benji Madden got married in 2015, and they’re so in love. In early 2020, the couple revealed that they welcomed their first child together — daughter Raddix.

Eva Longoria, 45, & Tony Parker, 38 

Eva Longoria
Eva Longoria and Tony Parker split in 2011 [AP Images].

Eva Longoria and Tony Parker were only married for three years, getting divorced in 2010, but they were one hot couple! Eva had the San Antonio Spurs star’s jersey number tattooed on her finger in lieu of a wedding band because she was so into him. Alas, some good things come to an end. They split officially because of “irreconcilable differences,” but rumors persist that he cheated. They’re both remarried and happy!

Sam Taylor-Johnson, 53, & Aaron Taylor-Johnson, 30 

Sam Taylor-Johnson, Aaron Taylor-Johnson
Sam and Aaron Taylor-Johnson share two daughters together [AP Images].

This is by far the largest age difference on the list. Sam Taylor Johnson, an acclaimed director, is a whopping 23 years older than her husband, actor Aaron Taylor-Johnson! The couple have spoken out about the age difference plenty of times, only affirming that they love each other. They also shared two daughters together. Take that, haters!

Cheryl, 37, & Liam Payne, 27

Cheryl, Liam Payne
Cheryl and Liam Payne were together in the mid-2010s [AP Images].

Cheryl‘s a legendary British pop star who recognized greatness in another one when he was just a teenager. Yes, Cheryl was a judge on X Factor when Liam Payne rolled through with One Direction, helping put the wheels in motion to make 1D a worldwide phenomenon. Years later, Cheryl and Liam reconnected. They were engaged and welcomed their son, Bear Payne, in March 2017. Sadly, they split in 2018.

Jennifer Lopez, 51, & Casper Smart, 33

Jennifer Lopez, Casper Smart
Jennifer Lopez & Casper Smart had an on-again, off-again relationship from 2011-2016 [AP Images].

Jennifer Lopez and Casper Smart’s had an on-again, off-again relationship that last for five years! At the time, Casper was one of J. Lo’s backup dancers, and the two took their relationship to a new level when they started dating in 2011. The pair eventually went their separate ways in 2016, when rumors began that she was seeing rapper Drake. Now, the “On The Floor” singer is half of one of Hollywood’s hottest couples! She’s been engaged to Alex Rodriguez, 45, since March 2019.

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Elon Musk Spotted At Airport In 1st Photos Since Being ‘Semi-Separated’ From Grimes

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Elon Musk


Elon Musk was spotted sipping a drink after landing at a private Los Angeles airport and leaving a building on the night of Sept. 24.

Elon Musk, 50, was photographed for the first time since his split from Grimes, 33, on the night of Sept. 24. The Tesla CEO left a building after landing at a private airport in Los Angeles, CA and appeared to be taking a sip of a drink at one point. He was wearing a black jacket over a black top and black pants and looked calm and relaxed as he walked by cameras. Check out the pics HERE.

Elon’s latest sighting happened just hours after he confirmed that he and Grimes, who share one-year-old son X Æ A-XII, separated after dating for three years. “We are semi-separated but still love each other, see each other frequently and are on great terms,” he told Page Six, adding that working on Space X in Texas keeps him traveling while she is staying “primarily in LA.”

Elon Musk during a previous outing. (Shutterstock)

“She’s staying with me now and Baby X is in the adjacent room,” he shared.

Before their separation, Elon and Grimes made headlines for attending the 2021 Met Gala earlier this month. Although she walked the red carpet alone, he joined her later on inside the event. They were also seen again while leaving New York City together with their dog and Grimes’ pink locks got some attention.

Grimes, Elon Musk
Grimes and Elon Musk post at a previous event. (Shutterstock)

When Elon isn’t making headlines for his personal life, he’s doing so with his company Space X. The company just successfully launched a historic all-civilian flight on Sept. 15 and it marked the first time people had traveled to space without an astronaut on board. It got the attention and praise of many impressive people, including Amazon’s Jeff Bezos, who publicly congratulated Elon for the big achievement.

“Congratulations to @ElonMusk and the @SpaceX team on their successful Inspiration4 launch last night. Another step towards a future where space is accessible to all of us,” he wrote in a tweet shortly after the launch.

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Dua Lipa Wears Miniskirt & Sweater With Nothing Underneath For Dinner With Gigi Hadid After Runway Debut

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Dua Lipa


Dua Lipa channeled the ’00s with this Versace logo skirt and bright cardigan as she headed to dinner with BF Anwar’s sister Gigi.

Dua Lipa, 26, having a serious fashion moment. Fresh off her catwalk debut, the British born singer once again donned Versace as as she headed to dinner at Ristorante La Briciola with boyfriend Anwar Hadid‘s sister Gigi, also 26, in Milan on Friday, Sept. 24. Dua left little to the imagination in the early aughts inspired look, which included a bright green cardigan sweater with nothing underneath, as well as a logo Versace skirt that served up some serious ’70s vibes with its groovy pink, green and yellow pattern.

Dua Lipa wears a Versace ensemble heading to dinner with Gigi Hadid. (
TABLOIT.IT / BACKGRID)

She added a satin pink mary jane shoe with a platform, as well as a matching pink leather bag. The outfit also perfectly matched her bright neon eye shadow, which she also rocked while sashaying down the catwalk for the first time ever. Finally, she switched up her hair and throw it back into a center parted bun, adding a chunky chain necklace as a finishing touch to the outfit.

Gigi Hadid
Gigi Hadid also stunned in burgundy. (TABLOIT.IT / BACKGRID)

Gigi also looked gorgeous in a burgundy outfit. The asymmetrical skirt, which featured a slit, and knotted crop top were made out of the same heavy cotton material. She accessorized with a black and silver chain belt, and a matching pair of chunky Prada loafers. The California native also opted to keep her hair back in a center parted bun.

Earlier in the day, Dua unexpectedly opened Versace’s Milan show, marking the first time the pop star has appeared in a fashion show. The “Levitating” singer recently shot a massive ad campaign for the iconic designer — which is helmed by the one and only Donatella Versace — to promote their Fall 2021 collection. In the photos, Dua looked wildly different with bright red hair. Notably, Gigi was also in the Versace show and likely gave the pop star plenty of pointers before her nerve wracking catwalk debut. Dua looked absolutely amazing as she modeled variousd looks from the brand, including a Barbie pink sequin ensemble.

The legendary Donatella recently reflected on her first time meeting Dua, which lead to their working relationship many years later. “I met Dua for the first time a few years ago in London. I knew she was a beautiful girl but when I heard the timbre of her voice. I realized immediately she had something unique and special,” she said in a statement back in June when the initial campaign was released. “Since then I’ve watched her career take off and partnered with her for many amazing moments. Right now, I cannot think of a better woman to embody the spirit of Versace and of this collection,” she added.

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John Zabel: 5 Things To Know About Britney Spears’ Potential New Conservator Replacing Dad Jamie

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Britney Spears


Britney Spears’ lawyer has named John Zabel, a CPA and business owner, as the candidate to temporarily replace Jamie Spears as conservator of the singer’s estate.

Britney Spears, 39, has her sights set on a new candidate to act as the temporary conservator of her estate. The singer and her lawyer, Mathew Rosengart, are fighting to remove Jamie Spears, 69, from his role as conservator of Brit’s estate and replace him with a temporary candidate before dissolving the conservatorship altogether. They had previously named licensed CPA Jason Rubin as their pick for the job, but on Sept. 23, Rosengart withdrew Jason’s nomination and suggested that John Zabel replace Jamie and temporarily control Britney’s finances and estate instead, according to The New York Times.

A decision on Britney’s conservatorship will likely be made at her next court date, which is scheduled for September 29. There, John may very well become the Grammy-winning singer’s temporary conservator of her estate. Here are five key things you need to know about John Zabel.

Britney Spears (Photo: Ken McKay/ITV/Shutterstock)

1. John owns his own company

John has a long list of credentials, starting with his position as the owner of Media Finance Structures, LLC (MFS). According to his LikedIn page, John has owned the company since March 2002. MFS offers “financial or operational management of entertainment projects,” the website states, and it has worked with major studios like Sony, Lionsgate, Parmount, CBS Films, and more. Of John, the company says, “John Zabel brings over three decades of industry experience to MFS, and is committed to delivering unbeatable client service and focused, tangible results.”

2. He’s a licensed CPA

John is a licensed Certified Public Accountant, just like Jason. He pursued accounting during his undergraduate years at CSU Long Beach in the early 1980s, and then later on completed the Exec. Management Program at UCLA in 1990. Considering the conservator of Britney’s estate would handle her finances, someone who is a CPA is ideal for the position.

3. He used to work as an Auditor

John’s first major job in accounting that is listed on his LinkedIn page is as a Senior Auditor for Arthur Young & Co. He held that position from 1981 to 1984. Then, John worked as a Senior Auditor for Ernst & Young from 1981 to 1984.

Jamie Spears
Jamie Spears (Photo: Shutterstock)

4. He was the Senior VP of Sony Pictures Entertainment

After he left Ernst & Young, John snagged a job at Sony Pictures Entertainment as the Senior Vice President. Sony Pictures Entertainment is headquartered in Culver City, Ca., and has an estimated revenue of $9.316 billion. It operates under Sony Pictures, which is one of the “Big Five” major film studios in the U.S.

John’s job at Sony was brief: he held the position from May 1984 to March 1995, and then moved on to work as Executive Vice President and Chief Financial Officer for Mandalay Entertainment from March 1995 to March 2002. After that, he created MFS.

5. He will have big responsibilities if he becomes Britney’s conservator.

John’s biggest task ever may be coming soon, if he is indeed named conservator of Britney’s estate. Jamie has held that job for over 13 years now, but amidst the #FreeBritneyMovement, he’s agreed to step down from his position. Britney’s personal conservator is Jodi Montgomery, who has also been onboard to dissolve Britney’s conservatorship. If John does replace Jamie, he’ll be in control of the singer’s finances and estate. That is all expected to be decided at the highly-anticipated Sept. 29 court date.

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