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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 Masked Singer’ Preview: The Russian Dolls Reveal A New Clue — Watch

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Russian Dolls


The Russian Dolls read a brand-new clue in this EXCLUSIVE preview of ‘The Masked Singer’ quarterfinals, and guest panelist Rob Riggle is convinced he knows their identities.

The quarterfinals have arrived on The Masked Singer, and the Russian Dolls will take the stage once again during the May 12 episode. After their performance, a new clue is revealed by “mail” sent by the biggest fan in this EXCLUSIVE preview. When host Nick Cannon opens up the mailbox, there’s another mailbox inside, a nod to the Russian Dolls.

One of the Russian Dolls reads the letter inside the second mailbox. “I was a fan of you individually, but when I saw you band together in person — wow! Like I can’t even. Love you to the moon and back again,” the letter says.

The Russian Dolls during the May 12 episode. (FOX)

Guest panelist Rob Riggle doesn’t believe he even needs this clue to guess the identities of the Russian Dolls. “Clues are for suckers. I don’t need them,” he says. He thinks he knows exactly who the Russian Dolls are.

“Bet this all day. Bet it twice on Sunday. That’s Devo,” Rob says. Devo is a rock band that rose to fame in the 1970s and 1980s. The band is best known for their hit song “Whip It.”

Nick isn’t convinced that Rob is right on this one. “Ken, this really is your friend,” Nick jokes. This makes Ken Jeong cackle.

The Russian Dolls
The Russian Dolls during their quarterfinals performance. (FOX)

The Russian Dolls changed the game from their very first performance of “The Man in the Mirror” by Michael Jackson. One Russian Doll started out singing the song, but a second Russian Doll later revealed himself during the performance. The Russian Dolls debuted a third member in the wildcard round. They’ve been stealing the show from the start.

The final 5 of season 5 are Russian Dolls, Chameleon, Black Swan, Piglet, and Yeti. At the end of the May 12 episode, one of the masked singers will be eliminated. The rest will move on to the season 5 semi-finals. The Masked Singer season 5 airs Wednesdays at 8 p.m. on FOX.

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‘Siesta Key’: Chloe Reveals Why She Left Season 4 After Filming Took A Toll On Her Mental Health

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siesta key


Previews for season 4 of ‘Siesta Key’ show Chloe Trautman announcing that she’ll be leaving the show in the middle of filming, and she dished all about it in our EXCLUSIVE interview.

“I’m at a point where I really don’t want to be a part of this anymore,” Chloe Trautman says in the trailer for season 4 of Siesta Key. “Farewell everyone.” While the details surrounding Chloe’s unexpected departure are still vague, she dished more about the decision in an EXCLUSIVE interview with HollywoodLife. In the months leading up to filming, Chloe underwent an extreme mental and physical lifestyle change. She lost 50 pounds and cut “toxic” people out of her life. However, when filming for Siesta Key began again in Nov. 2020, she noticed that the “old Chloe” was starting to come back.

“In that environment, I have always been the ‘old Chloe,’ and it was like oil and water mixing filming and the new me,” she explained. “Well, I don’t like to say ‘new me,’ I like to say ‘true me.’ This season, you really see that battle of me trying to stay the course with the internal work that I’ve done. But I’m not perfect and I definitely have some bumps this season. Overall, I’m really proud of myself for putting myself out there and putting my mental health first. I think, more than ever, that’s such an important message to send — no matter what you’re doing in your life, if you’re placing yourself in an environment that’s not for your highest good, walk away from it. I’m just proud that I’ll represent that this season.”

Chloe did make the difficult decision to walk away. She said that the lack of support from her friends, who were skeptical about her transformation, was what ultimately led to the decision. “They weren’t as supportive as I think they could’ve been,” Chloe admitted. “Understandably, they were skeptical — they were wondering if this was just a phase. But for me, it just really built up. Every week, all the cast parties we’d go to, it would just build up over and over and over again. It just got to a point where I was like, ‘Alright, guys, stop trying to tear me down.’ When I didn’t feel like I had enough support from my friends and cast and production, I took a big step back.”

Luckily, it was the right decision, and Chloe told that it was “extremely necessary” for her. “I feel like I did the most work on myself in that time when I took a step back,” she revealed. “To me, in your true power, you should be able to place yourself in any environment and still stand true to who you are.”

The cast of season 4 of ‘Siesta Key’. (MTV)

Chloe also dished about the “breaking point” that led her to transform her lifestyle and become the person who she is today. “[In March 2020], our friend group went to Aspen and I was 50 pounds heavier than I am right now,” she explained. “I was skiing down a mountain and I was so out of shape, and I ended up falling and really hurting myself. It was in that moment that I cried out to God for help. Then, I went through a breakup with my ex-boyfriend of almost four years and my grandmother, who passed away, came to me and spoke to me on her birthday in June. My life just changed. The right people started to come into my life. I stopped drinking. I stopped partying. I really stepped back from any toxic environment or friendships I was in, too.”

Now, Chloe is “really excited” to show Siesta Key viewers the new version of herself. “I can’t wait to show people how, when you heal yourself, it’s truly the greatest thing you can ever do,” she gushed. “And how important it is to take time for yourself and mental health and meditating and all those beautiful things.” Siesta Key returns on May 12 at 8:00 p.m. on MTV.



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Tom Brady Honors Ex Bridget Moynahan On Mother’s Day With Blended Family Photo

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Tom Brady Honors Ex Bridget Moynahan On Mother’s Day With Blended Family Photo


On Mother’s Day, Tom Brady made sure to honor the women he thinks are the ‘greatest of all time’ – his wife, Gisele Bündchen, and his ex – and mother of his oldest son — Bridget Moynahan.

Tom Brady didn’t leave anyone out of his Mother’s Day messages. On Sunday (May 9), the NFL icon took time to honor all the amazing mothers in his life, including his ex, Bridget Moynahan. “Happy Mother’s Day,” Tom, 43, captioned a photo he posted to his Instagram Stories. In the pic, Tom and his wife, Gisele Bündchen, stand next to his 13-year-old son, Jack, and his mother. It was a sweet, blended family photo and a lovely sentiment from Tom to his ex-girlfriend on this special day.

The Tampa Bay Buccaneers quarterback also paid tribute to Gisele, 40, in his Instagram Story (“My numero uno,” he captioned a photo of the supermodel snuggling her and Tom’s kids, Ben, 11, and Vivian, 8) and with a touching post that featured all his kids. “Happy Mother’s Day, [Gisele],” Tom captioned the black and white shot of all five of them on the beach. “You love us and support us like no other. Have a special day! [heart emoji] [heart emoji].”

Along with Bridget and Gisele, Tom celebrated his mother, 76-year-old Galynn Patricia Brady. Tom posted a photo of Gisele hugging Gaylnn. “Happy Mother’s Day [heart emoji] to the best moms in the world!!”

Though Tom and Bridget called it quits in late 2006, the two have remained on good terms. However, it’s not every day that Tom makes a public gesture of affection towards his ex, so it was quite a moment when he wished her a “Happy Birthday” on April 29. That day, Bridget turned 50, and Tom celebrated by posting a photo of her alongside their son Jack to his Instagram Story. “Happy Birthday,” he captioned the photo. “We hope you have a great day!”

Bridget Moynahan and Tom Brady attend the VANITY FAIR PARTY AT THE 2005 ACADEMY AWARDS (Shutterstock)

Months after Tom and Bridget split, the couple revealed that she was pregnant with his child. She gave birth to Jack in August 2007, right as Tom was starting his relationship with Gisele. “It was very hard for my wife to think she fell in love with this guy, and now this guy’s ex-girlfriend’s pregnant,” he said in a 2020 interview. “And it was very challenging for my son’s mom because she didn’t envision that either. But I think we all made the best of the situation, and fortunately, he’s the most amazing son.”



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