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How Cara Delevingne Became Hollywood’s Biggest Heartbreaker

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This year’s Oscars was widely seen as a sleepy wokefest, but it looks like the most entertaining drama to win took place at a private party.

Especially when overtly pansexual Model Cara Delevingne, 28, was seen leaving an Oscar afterparty and cramming into a car with singer Paris Jackson, once again sparking rumors of a romance between the duo. Page Six exclusively reported as the couple smiled as Jackson tried to cover his face.

The couple have been linked occasionally since 2017, when they were spotted leaving a nightclub hand in hand. Delevingne started squirting the youngest model around town, attending a Burberry party together and spied on smooching at a dinner with Jackson’s godfather Macaulay Culkin and his girlfriend Brenda Song.

TAKING CARA'S BUSINESS: Cara Delevingne (left) and girlfriend Ashley Benson teamed up to transport a kinky sex bench to their Los Angeles home in 2019.
TAKING THE CARA COMPANY:Cara Delevingne (left) and girlfriend Ashley Benson teamed up to transport a kinky ‘sex bench’ to their Los Angeles home in 2019.
GAC / MEGA

If they are truly dating, Jackson failing to identify his sexuality would be just the latest in a string of stunning ladies on Delevingne’s arm.

The “Paper Towns” actress has carved out a niche in Hollywood normally reserved for Lotharios men like Leo DiCaprio and, before him, Warren Beatty. For nearly a decade, Delevingne has shamelessly enjoyed public relations and sometimes just exciting flirtations with a multitude of beautiful, high-profile women.

“I think she just looks that way, because she’s both feminine and masculine,” a global model source told The Post of Delevingne. “She’s powerful, connected and successful. If you’re a lesbian or sexually fluid, you definitely have a crush on her. She’s so cool and just magnetic.


Born in London into an aristocratic family (her grandmother was a maid of honor to Princess Margaret), Delevingne has always been plugged into high society. Her father Charles is a real estate developer and her mother Pandora is friends with Sarah Ferguson, Duchess of York. Her godmother is “Dynasty” actress Joan Collins.

In 2009, she was hired at Storm Management by founder Sarah Doukas, who also discovered Kate Moss, then 14, at JFK while she was on vacation. But unlike the Moss working class, Delevingne was no accidental stranger to the Doukas.

I have been the best friend of Genevieve Garner, daughter of Sarah Doukas, since the age of 5, Delevingne told the British Telegraph.

Kendall Jenner and Delevingne (pictured in 2018) are catwalk pals who once walked the Chanel runway hand in hand and even created a line of t-shirts based on their names called CaKe.
Kendall Jenner and Delevingne (pictured in 2018) are catwalk pals who once walked the Chanel runway hand in hand and even created a line of t-shirts based on their names called CaKe.
Madison Voelkel / BFA.com

She left school to pursue a career, and by 2012 had become the most sought-after face in modeling, rocking the industry with her chenille eyebrows, androgynous energy, and rebellious streak.

Former fashion executive and ‘Leave Your Mark’ podcast host Aliza Licht recalls working with Delevingne in 2014, when the show had a collection with DKNY. At the launch event, they asked her to stand on top of the Bloomingdale marquee.

“Everyone was pretty nervous seeing her get up in the air like that, so we had an ‘X’ marked to show her where she could safely stand,” Licht told the Post.

In July 2020, Delevingne started a PDA friendship with Cindy Crawford's model daughter Kaia Gerber (right), who was 18 at the time.
In July 2020, Delevingne started a PDA friendship with Cindy Crawford’s model daughter Kaia Gerber (right), who was 18 at the time.
Entertainment in London / Shutterstock

“She completely ignored him. She went to the edge and had the best time with the hundreds of fans who showed up for the launch. She’s a renegade, that’s for sure.


When she first burst onto the style scene, she was linked to Harry Styles.

But just as she rocked the fashion world, she helped change the conversation about sexual orientation, sometimes against a lawyer.

In an interview with Porter magazine, Delevingne revealed that disgraced producer Harvey Weinstein advised him to stay in the closet, telling him, “You’re never going to be successful in this industry as a gay woman with a beard.”

She not only rejected that advice, she did it cheekily.

In early 2014, Delevingne was photographed during a Knicks game with actress Michelle Rodriguez from “The Fast and the Furious”.

Michael Jackson's daughter Paris (left) and Delevingne were spotted leaving the home of art collector Eugenio Lopez in Beverly Hills after the Oscars last week.
Michael Jackson’s daughter Paris (left) and Delevingne were spotted leaving the home of art collector Eugenio Lopez in Beverly Hills after the Oscars last week.
Instagram

But in July, the couple broke up, and in March 2015, Delevingne was hanging out with singer Annie Clark, aka St. Vincent. About a month into the relationship, she tweeted, “I’m very in love,” topped with a heart-shaped emoji.

That same month, she was on the cover of Vogue and opened up about her relationship and fluid sexuality.

I think being in love with my girlfriend is a big part of why I feel so happy with who I am these days. And for these words to come out of my mouth is actually a miracle. . . It took me a long time to come to terms with the idea, until I fell in love with a girl at 20 and admitted that I had to come to terms with it, she told the magazine.

She added that she had erotic dreams about men and that she was ready to marry a man and have children.

The article also noted that her parents thought dating girls might be a phase. In a later profile in the New York Times, she proclaimed, “My sexuality is not a phase.”

All the while, however, her model sister supported her.

“When she spoke to her older sister Poppy, she was fully supportive,” the models source said.


The first woman Delevingne (left) openly dated was Annie Clark aka Saint Vincent.  They attended the Burberry show together in September 2015.
The first woman Delevingne (left) openly dated was Annie Clark aka Saint Vincent. They attended the Burberry show together in September 2015.
David M. Benett

In September 2016, news began to circulate that she and Clark had separated. Delevingne was then linked to Amber Heard, who at the time was in the middle of a messy divorce with Johnny Depp. In 2017, she hit it off with Jackson after they met at the MTV Movie & TV Awards.

In May 2018, “Pretty Little Liars” actress Ashley Benson posted a selfie with Delevingne. The couple both starred in “Her Smell,” a group movie starring Elisabeth Moss, Benson and Delevingne’s supposed lover, Heard and were seen leaving. Kylie Jenner 21st Birthday together.

The model was then pictured kissing Benson’s neck by a parking meter. They have been spotted on vacation in the Maldives, and pictures of them wearing a “sex benchIn Delevingne’s house became an Internet tradition, although they were still shy about their affair.

Delevingne is often openly intimate with friends who aren't dating, like Rihanna (at the British Fashion Awards in 2014).
Delevingne is often openly intimate with friends who aren’t dating, like Rihanna (at the British Fashion Awards in 2014).
Getty Images

The naughty affair was Benson’s first with another woman, according to us weekly.

On RuPaul’s “What’s the Tee” podcast, Delevingne revealed that she is an assertive lover when it comes to women, perhaps offering glimpses of her ability to attract allegedly heterosexual women to the other side.

“This whole process of courting power is very interesting. And that’s a difference with men and women. I am always very submissive with men. Always. But with women, I’m the opposite, ”she says.

In a June 2019 Instagram post, Delevingne admitted that she and Benson were a couple, later commenting on her reasons for going public: I don’t know [if it’s] because it’s Pride, it’s been 50 years since Stonewall arrived and I don’t know. It was about our one year anniversary, so why not?

Her shmoopy nickname for Benson? Water.


However, the couple will not survive the pandemic and went their separate ways in May 2020. Benson quickly moved on with rapper G-Eazy while months later, the sun brought back that Delevingne kissed G-Eazy’s ex, singer Halsey.

Between her confirmed romances there are flashes of romantic encounters with models and actresses and suggestive social media posts.

Miley Cyrus and Cara Delevingne hung out backstage at the Marc Jacobs fashion show in New York in 2013, and months later they locked tongues on an Instagram photo.
Miley Cyrus and Cara Delevingne hung out backstage at the Marc Jacobs fashion show in New York in 2013, and months later they locked tongues on an Instagram photo.
Miley Cyrus / Twitter

There were pictures of her arm in arm with Dakota johnson and snuggle up with Margaret qualley.

She loves to flirt on red carpets, even with people she’s not romantically involved with, from her girlfriend Rihanna to Prince Harry.

In 2020, she and Kaia Gerber both had matching “Solemates” tattoos on their feet and were seen draped over each other at many times. At one point, Delevingne was even linked to Selena Gomez, while the couple frolicked around southern France in 2014. They weren’t dating.

But in 2015, Gomez says PrideSource she was very satisfied with the association.

Honestly, though, she’s amazing and very open, and she just makes me open. . . She’s so fun, and she’s just extremely adventurous, and sometimes I just want that in my life, so I didn’t mind, ”Gomez said. “I liked it.

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