How Cara Delevingne became Hollywood’s biggest heartbreaker

How Cara Delevingne became Hollywood’s biggest heartbreaker

This year’s Oscars were widely panned as a snoozy wokefest, but it seems the most entertaining award-worthy drama was happening during a private soiree.

Particularly when openly pansexual model Cara Delevingne, 28, was seenleaving an Oscars afterparty and piling into a car with singer Paris Jackson, once again sparking rumors of a romance between the duo. Page Six exclusively reported that the pair were smiling while Jackson attempted to cover her face.

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

TAKING CARA BUSINESS: Cara Delevingne (left) and girlfriend Ashley Benson tag-teamed to cary a kinky “sex bench” into their Los Angeles home in 2019.TAKING CARA BUSINESS: Cara Delevingne (left) and girlfriend Ashley Benson tag-teamed to cary a kinky “sex bench” into their Los Angeles home in 2019.GAC / MEGA

If they are indeed dating, Jackson — who does not label her sexuality — would be just the latest of a string of stunning ladies on Delevingne’s arm.

The “Paper Towns” actress has carved out a niche in Hollywood normally reserved for male Lotharios like Leo DiCaprio and, before him, Warren Beatty. For nearly a decade, Delevingne has been unapologetically enjoying public relationships and sometimes just titillating flirtations with a bevy of high profile, beautiful women.

“I think she just has this allure, because she’s both feminine and masculine,” a modeling world source told The Post of Delevingne. “She’s powerful, connected and successful. If you are a lesbian or sexually fluid, you definitely have a crush on her. She is so f – – king cool and just magnetic.”


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

In 2009, she was signed to Storm Management by founder Sarah Doukas, who also discovered a then-14-year-old Kate Moss at JFK while she was on vacation. But unlike the working-class Moss, Delevingne wasn’t a random stranger to Doukas.

“I’ve been best friends with Genevieve Garner, daughter of Sarah Doukas, since I was 5,” Delevingne explained to the UK’s Telegraph.

Kendall Jenner and Delevingne (pictured in 2018) are catwalk cronies who once strutted the Chanel runway hand-in-hand and even created a T-shirt line based on their names called CaKe.Kendall Jenner and Delevingne (pictured in 2018) are catwalk cronies who once strutted the Chanel runway hand-in-hand and even created a T-shirt line 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, shaking up the industry with her trademark caterpillar eyebrows, androgynous energy and rebellious streak.

Former fashion executive and host of “Leave Your Mark” podcast Aliza Licht recalled working with Delevingne in 2014, when the catwalker had a collection with DKNY. During the launch event, they asked her to stand atop the Bloomingdale’s marquee.

“Everyone was pretty nervous about having her stand 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 debuted a PDA friendship with Cindy Crawford’s model daughter, Kaia Gerber (right), who was 18 at the time.In July 2020 Delevingne debuted a PDA friendship with Cindy Crawford’s model daughter, Kaia Gerber (right), who was 18 at the time.London Entertainment/Shutterstock

“She completely ignored it. She went right to the edge and had the best time engaging with the hundreds of fans who showed up for the launch. She is a renegade, for sure.”


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

But just as she shook up the fashion world, she helped change the conversation around sexual orientation — sometimes against counsel.

In an interview with Porter magazine, Delevingne revealed that disgraced producer Harvey Weinstein advised her to stay in the closet, telling her, ” ‘You will never make it in this industry as a gay woman — get a beard.’ ”

She not only rejected that advice, she did so brazenly.

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

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

But by July, the pair had split and in March 2015, Delevingne moved on with singer Annie Clark, a k a St. Vincent. About a month into the relationship, she tweeted, “I am very much in love,” capped with a heart emoji.

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

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

She added that she has erotic dreams about men and is open to marrying a man and having children.

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

Throughout this time, however, her model sister had her back.

“When she came out to her older sister Poppy, she was fully supportive,” the modeling 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 started to circulate that she and Clark had split. Delevingne was then linked to Amber Heard, who at the time was in the midst 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 pair were both cast in “HerSmell” — a flick about a band starring Elisabeth Moss, Benson and Delevingne’s rumored paramour Heard — and were seen leaving Kylie Jenner’s 21st birthday party together.

The model was then photographed kissing Benson’s neck by a parking meter. They were spotted vacationing in Maldives, and photos of them carrying a “sex bench” into Delevingne’s house has become internet lore, although they were still coy about their liaison.

Delevingne is often openly intimate with friends she’s not dating, such as Rihanna (at the British Fashion Awards in 2014).Delevingne is often openly intimate with friends she’s not dating, such as Rihanna (at the British Fashion Awards in 2014).Getty Images

The saucy affair was Benson’s first with another woman, according to Us Weekly.

On RuPaul’s “What’s the Tee” podcast, Delevingne divulged that she’s an assertive lover when it comes to women, perhaps offering insight into her ability to lure supposedly straight ladies to the other side.

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

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

Her shmoopy nickname for Benson? Sprinkles.


However, the couple would not survive the pandemic, and split in May 2020. Benson quickly moved on with rapper G-Eazy while months later, the Sun reported that Delevingne has kissed G-Eazy’s ex, the singer Halsey.

In between her confirmed romances are flashes of flirty encounters with models and actresses and suggestive social-media posts.

Miley Cyrus and Cara Delevingne hung out backstage at Marc Jacobs’ fashion show in NYC in 2013, and just a couple of months later, they locked tongues in an Instagram pic.Miley Cyrus and Cara Delevingne hung out backstage at Marc Jacobs’ fashion show in NYC in 2013, and just a couple of months later, they locked tongues in an Instagram pic.Miley Cyrus/Twitter

There were pictures of her arm in arm with Dakota Johnson and snuggling with Margaret Qualley.

She loves to flirt it up on red carpets — even with people she’s not linked to romantically, from her pal Rihanna to Prince Harry.

In 2020, she and Kaia Gerber both got matching “Solemates” tattoos on their feet and were seen draped all over each other on numerous occasions. At one point, Delevingne was even linked to Selena Gomez, while the pair frolicked through the South of France in 2014. They were not dating.

But in 2015, Gomez told PrideSource she was quite pleased with the association.

“Honestly, though, she’s incredible 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 it,” Gomez said. “I loved it.”