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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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The Queen Wipes Away Tears As She Arrives At Husband Prince Philip’s Funeral — See Photo

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queen elizabeth



Queen Elizabeth was emotional as she arrived at her late husband Prince Philip’s funeral at Windsor Castle. See all the photos.

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Brittany Matthews Shows Off Her Post-Baby Body In Fierce Orange Outfit 2 Months After Giving Birth

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Brittany Matthews Jackson Mahomes


Brittany Matthews came to slay in an orange blazer and mini skirt during a night out at Nobu. The new mama showed off her legs for days just two months after giving birth.

Hot mama alert! Brittany Matthews got gussied up for a night on the town in West Hollywood, and her post-baby style is sizzling. Just two months after giving birth to daughter Sterling Skye Mahomes, Brittany rocked a mini skirt and fitted blazer that showed off her already slim figure. The bright orange skirt suit, paired with a white tank top and ankle boots, gave off major mod vibes.

Brittany Matthews rocks an orange blazer while leaving dinner with future BIL Jackson Mahomes, 4/15/21 (HEDO/BACKGRID)

The new mom, 25, definitely deserved her April 15 dinner at Nobu. Accompanied by future brother-in-law Jackson Mahomes, she looked like she was having a blast. Brittany and her fiancé, NFL star Patrick Mahomes, 25, welcomed their baby girl into the world on February 21. They announced the joyous news on Instagram with a photo showing a tiny hand clutching Brittany’s finger in the hospital. The new mama wore a sparkly “Sterling” necklace.

The happy couple have shared plenty of adorable photos and videos of their first child on Instagram over the past two months. In early March, Brittany shared a cool video showing her baby bump progression during her trips to the gym. At the end, she’s cradling little Sterling on her flattened stomach. So cute!

Brittany Matthews Jackson Mahomes
Brittany Matthews and Jackson Mahomes’ fun night came two months after she gave birth (HEDO/BACKGRID)

Patrick was over the moon about becoming a first-time father. Just two weeks before Brittany gave birth, he expressed his joy in an interview with 610 Sports Radio Kansas City. “I mean really, anytime, I could be having a baby girl, and I’m super excited about that. It’s gonna be something special, and I’m excited for the journey of trying to find ways to better myself and become the best dad that I can be,” he said.

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​Lori Loughlin Delivers Food To Those In Need 3 Months After Prison Release — Pic

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​Lori Loughlin Delivers Food To Those In Need 3 Months After Prison Release — Pic


Lori Loughlin spent some time on April 14 delivering food with Project Angel Foods. See the latest photos of the former actress, who was released from prison at the end of December 2020.

Lori Loughlin kept a low-profile while volunteering in Los Angeles on April 14. The former Full House actress, 56, was spotted wearing a pair of blue jeans, a cream-colored sweater with 3/4 length sleeves, a face mask and baseball cap while out volunteering. Lori has been working with Project Angel Foods and delivering items to those in need, just over three months since her prison release.

Lori Loughlin is spotted volunteering at Project Angel Foods in Los Angeles after husband Mossimo Giannulli is freed from jail on April 14, 2021 [SplashNews.com].

This isn’t the first time that Lori has been spotted out and about, as she completes her 100 hours of community service that was designated along with her guilty plea. In fact, Lori was photographed driving her SUV in Calabasas, CA, on Thursday, April 8, just after her husband, Mossimo Giannulli, was released from prison and transitioned to home confinement on April 2. It’s been quite a whirlwind for the couple, who pled guilty in May 2020 to one count of conspiracy to commit wire and mail fraud by paying college admissions counselor Rick Singer over $500,000 in order to secure their daughters, Olivia Jade, 21, and Isabella Rose, 22, spots at the University of Southern California.

Lori served two months of her prison sentence, while Mossimo served five months. Along with serving time in prison, both Lori and Mossimo paid fines for their illegal actions. Lori paid $150,000 while Mossimo paid $250,000 in November 2020. Lori has been partnering with Project Angel Foods for some time, and was actually spotted delivering foods and services in early March.

Lori Loughlin was released from prison after serving a two-month sentence for involvement in the college admissions scandal. She is currently completing her 100-hour community service [Steven Senne/AP/Shutterstock].

Along with Lori and Mossimo settling back into their new normal, the couple’s daughters have also been repairing their own reputations. Olivia has been vocal about her part in the college admissions scandal, and for that Lori is proud. “Lori is so proud of Olivia for continuing to speak out,” a source shared EXCLUSIVELY with HollywoodLife in late March 2021.

“[Lori] wants to be able to speak out, but really wants to control the narrative and have Mossimo home [first],” the insider continued. “[But] she is closer with her daughters than ever right now.” Mossimo will begin completing his 250 hours of community service after April 17, a few short weeks after settling back at home.

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