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Cara Delevingne's Complete Dating History

Cara Delevingne and Kendall Jenner pose together at a party
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Mar. 24 2020, Updated 2:34 p.m. ET

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Model and actress Cara Delevingne is known for her kick-ass style, trendsetting eyebrows and outspoken wit ... as well as her steamy dating history. The Paper Towns star can count many Hollywood A-listers as a notch on her belt, but is she really ready to settle down? Hopefully so since Delevingne reportedly just married Ashley Benson in Las Vegas!

More: Get all the details on Cara Delevingne and Ashley Benson’s Elvis-themed wedding

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Delevingne has been open about her sexuality, revealing that she doesn’t like to be pigeonholed into dating only men or women, which is evident by taking a look at her past and present relationships. From her new wife Ashley Benson, to Fast and Furious actress Michelle Rodriguez and then to rumored flings with Harry Styles and Kendall Jenner, we break down the timeline of Delevingne’s hot dating history.

More: Stripped down! See Cara Delevigne’s Nearly Nude Instagram Selfies

Ready to dive in? Take a look at 12 people who have been linked to the sexy model.

Did Delevingne Break Jake Bugg’s Heart?

Cara Delevingne and Jake Bugg pose together at a party.
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Delevingne met indie singer-songwriter Jake Bugg at a Burberry party when she was the newest “it” model in 2013. The pair hit it off immediately and were immediately hot and heavy … until they weren’t. Delevingne, who was 21 at the time, broke it off with Bugg and — a source later reported — that he was “very upset” that their relationship had ended.

As for Delevingne, 2013 turned out to be a busy year in the romance department for The Suicide Squad actress.

Was Rita Ora Her First Love?

Cara Delevigne in a sparkly dress and singer Rita Ora in a black dress pose together
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One of the model’s first female loves appears to be pop singer Rita Ora, who had a close relationship with Delevingne in 2013. opened up to Vogue magazine about her sexuality.

“When I first realized that gender is so much more fluid than ‘masculine’ or ‘feminine’ it was a breakthrough moment for me.”

Ora called her “wifey” and said she’s “taken her off the market.” The singer’s racy song “Girls” is reportedly about her relationship with Delevingne.

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Did Delevingne Have A Fling with Harry Styles?

Cara Delevigne stares affectionally at singer Harry Styles
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The year of 2013 continued to be hot and heavy for Delevingne. She was next linked to former One Direction singer Harry Styles. He was spotted sitting front row cheering her on with some other of her good friends during Fashion Week. She later posted a cute picture of them together backstage, which created even more buzz about their possible relationship.

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Did She Date Leonardo DiCaprio?

Leonardo DiCaprio in a suit at the HBO Ice On Fire Premiere
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Everyone knows it is a supermodel rite of passage to date Leo, and Delevingne and DiCaprio were spotted chatting at Cannes while he was promoting his movie, The Great Gatsby. Sources spilled that he was “begging” her to go back to his hotel room with him, and although she reportedly declined, she did pass on her number to the Oscar winning actor ... but perhaps it was just to talk upcoming movies?

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Are Paris Hilton And Delevingne More Than Just Friends?

Paris Hilton poses in a sheer floral gown in Cannes
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DiCaprio wasn’t the only celebrity who had his eye on Delevingne in Cannes that year. The supermodel was also spotted hanging out with Paris Hilton. In fact, the two were photographed leaving a party together early in the morning with their arms around each other. Perhaps they were just holding each other up after a long night of partying — or maybe it was something more?

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Did Delevingne And Miley Cyrus Hook Up?

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Cara Delevigne and Miley Cyrus spotted entering a party together
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Miley Cyrus heated up the internet when she posted a picture of the singer making out with Delevingne.

"LOVE!!!!! We finally got the filmed developed Mush," she tweeted, posting a picture of the two girls touching tongues.

Maybe they were just friends having fun together, or perhaps it was something more? Neither party confirmed or denied their involvement, and Cyrus has since moved on to Kaitlynn Carter since breaking up with her husband Liam Hemsworth.

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Was Rihanna Her New Year’s Eve Kiss?

Rihanna and Cara Delevingne look gorgeous at a movie premiere in LA
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Delevingne ended her busy year by ringing in 2014 with her bestie and rumored love interest, Rihanna, as the couple were spotted spending time together in Barbados. They spent the day lounging on the beach, followed by a romantic dinner and ending with … a New Year’s kiss, perhaps?

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Was Michelle Rodriguez Her First Serious Relationship?

Actress Michelle Rodriguez wears white pants paired with a eye catching white blazer
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After her 2013 dating spree, Delevingne settled down in 2014 with The Fast and the Furious actress Michelle Rodgrigez. The couple were spotted getting cozy at the zoo and a basketball game. Rodriguez, who is 14 years older than Delevingne, gushed to the Mirror about the British supermodel.

“It’s going really well. She’s so cool. When we started hanging out I just thought she was awesome, and we have the best time together.”

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Did A Steamy Photo Session with Kendall Jenner Result in a Relationship?

Kendall Jenner and Cara Delevigne pose together in Chanel sunglasses
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Tongues immediately started wagging as Love magazine revealed their September cover, which featured Delevingne and Kendall Jenner in a steamy embrace. To add fuel to the fire, the models were also spotted holding hands at a fashion show. Was it just a friendship … or something more? Either way, they do look stylish together!

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Did Delevingne Fall Head Over Heels in Love with St. Vincent?

Cara Delevigne, dressed in a suit, poses with singer St. Vincent
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Delevingne seemed to find true love and finally settled down in 2015 with singer Annie Clark, who goes by her stage name of St. Vincent.

She gushed to Vogue that she was “completely in love” with St. Vincent.

"As a child, I used gay as a bad world, as in, 'that's so gay.' All my friends did," she said. “I'm obviously in love, so if people want to say I'm gay, that's great. But we're all liquid - we change, we grow."

The pair dated for over a year before breaking up ... reportedly due to the struggles of a long distance relationship.

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Did Delevingne Rebound From St Vincent With Paris Jackson?

Paris Jackson poses at the premiere of Peanut Butter Falcon
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After meeting at the MTV Movie Awards, Delevingne and Paris Jackson started spending time together in 2018. They weren’t shy about showing PDA as they were spotted kissing and dancing outside of a restaurant. Paris, who is the daughter of Michael Jackson, posted a picture of them together around Christmas and even included a sweet poem as the caption.

Shortly after Delevingne’s 26th birthday, the pair fizzled out with Paris tweeting, “girls smh,” reportedly directed at Cara for ending their relationship.

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Are Delevingne And Ashley Benson Still Going Strong?

Cara Delevigne and her girlfriend Ashley Benson leave an event together
Source: LAURENT BENHAMOU/SIPA/Shutterstock

Delevingne and Pretty Little Liars star Ashley Benson have been dating since last year, and they reportedly have just gotten married! Engagement rumors heated up after they were spotted wearing matching gold rings after a vacation to St. Tropez. Benson also revealed a “CD” tattoo under her left arm on Instagram, which fans quickly pointed out was for her girlfriend.

The secret Elvis-themed wedding in Las Vegas and was an intimate affair with friends like Charlize Theron and Sophie Turner in attendance. Congrats to the happy couple!

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