By Lucy Cooper

2nd April 2019

Cara Delevingne and Ashley Benson’s relationship timeline:

May 2018: the month Britain’s most exuberant supermodel – Cara Jocelyn Delevingne – hit the headlines with yet more relationship rumours.

Just another day in the life of Ms Delevingne

And the latest ‘allegedly’ on her list? Pretty Little Liar’s actress and stunner, Ashley Benson.

“I think it’s the best way in any relationship. I’ve always been very private about them, and I think it’s just better.’’

Ashley Benson


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Fast forward 10 months down the line: 10 months of coy Social Media posts; 10 months of candid paparazzi photos; and 10 months of actively avoiding any definitive confirmation of their relationship status – and here we are, still none the wiser on the details of the hottest celebrity couple still storming and dominating the celeb scene…

But why the obsession? Are we oddly (and a little bit too) intrigued in this ‘coupling’ due to Cara Delevingne and Ashley Benson’s infuriatingly good looks?

Or is it the fact it is Ashley’s first same-sex – and consequently self ‘outing’ – relationship?

Or is it due to the pair’s (selfish) reluctance to share the ins and outs of their relationship with a globe of nameless, anonymous and unknown people (yes, we mean you – and us), who will shamelessly cast judgements on every aspect of their blossoming relationship?



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post show cuddle puddle 👩‍❤️‍👩 @chanelofficial

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What originally began as an innocent outing of ‘two friends’ to a concert in New York City back in May of last year, rapidly developed and advanced into modern day Romeo and Juliet territory – the secrets, the sneaking around, the blatant chemistry between the pair.

And here we are…still here…just desperately trying to receive any slight authentication on the most enviable celebrity couple of this decade…

Nevertheless, the ‘couple’ have been unable to keep their ‘relationship’ completely under wraps (much to the dismay of Cara Delevingne’s rumoured girlfriend). Speaking to PEOPLE Now, Ashley stated:

“I mean it’s hard, I don’t know, you kind of can’t get away from that if you’re in the public eye.” 

“I just kinda try to keep myself as private as possible.”

“That’s one good thing about living in New York — I can live kind of a normal lifestyle… in L.A., the paparazzi are really bad, but here I can kind of just walk anywhere and not be bothered.”

Need we remind Ash how her relationship was first discovered? A paparazzi shot…in New York…

Despite the fact we are already quite familiar with the goddess that is Cara Delevingne – the youngest British model to challenge the legacy of Kate Moss; the supermodel flying the flag for the British in the infamous Victoria Secret catwalk; the surprisingly talented actress, making her film debut in Paper Towns; the fashion icon continuously providing outfit envy (cue the Armani suit and top had she exhibited to Princess Eugenie’s wedding) – we are still less than satisfied on our knowledge of her relationship with Ashley Benson.

Yet we cannot deny that Cara Delevingne is a true icon/idol for young females, further proving this when bravely revealing that she was Sexually harassed by Harvey Weinstein in the early days of her career, as an act of tackling mental health issues in the youth of today.


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When I first started to work as an actress, i was working on a film and I received a call from‎ Harvey Weinstein asking if I had slept with any of the women I was seen out with in the media. It was a very odd and uncomfortable call….i answered none of his questions and hurried off the phone but before I hung up, he said to me that If I was gay or decided to be with a woman especially in public that I’d never get the role of a straight woman or make it as an actress in Hollywood. A year or two later, I went to a meeting with him in the lobby of a hotel with a director about an upcoming film. The director left the meeting and Harvey asked me to stay and chat with him. As soon as we were alone he began to brag about all the actresses he had slept with and how he had made their careers and spoke about other inappropriate things of a sexual nature. He then invited me to his room. I quickly declined and asked his assistant if my car was outside. She said it wasn’t and wouldn’t be for a bit and I should go to his room. At that moment I felt very powerless and scared but didn’t want to act that way hoping that I was wrong about the situation. When I arrived I was relieved to find another woman in his room and thought immediately I was safe. He asked us to kiss and she began some sort of advances upon his direction. I swiftly got up and asked him if he knew that I could sing. And I began to sing….i thought it would make the situation better….more professional….like an audition….i was so nervous. After singing I said again that I had to leave. He walked me to the door and stood in front of it and tried to kiss me on the lips. I stopped him and managed to get out of the room. I still got the part for the film and always thought that he gave it to me because of what happened. Since then I felt awful that I did the movie. I felt like I didn’t deserve the part. I was so hesitant about speaking out….I didn’t want to hurt his family. I felt guilty as if I did something wrong. I was also terrified that this sort of thing had happened to so many women I know but no one had said anything because of fear.

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Her Suicide Squad co-star, Margot Robbie, praised Cara on her bravery for speaking out:

“Cara Delevingne is a dear friend of mine and I already knew she was a fierce, brave woman. Today just proved that again.” 

We know the ins and outs of her modelling career, we know what movies Delevingne starred in, we even know her preferences in the bedroom – but what we want to know is the sordid details of her relationship with Ashley Benson.

They undeniably have ‘something’ going on, whether they are willing to admit it or not – and although we may be far too invested, what harm would Delevingne-ing further into the enigmatic relationship of Cara Delevingne and Ashley Benson really do us?

Sneaky Heathrow Airport pap photos; subtle Social Media references to one another; supportive front row seating at fashion shows; 3rd party Social Media postings? We have got it all covered…

1st May 2018: Cara And Ashley’s First Outing Together

Back where it all began – the supermodel and Pretty Little Liars actress first set tongues wagging when they stepped out together to attend a Lauryn Hill concert in New York. At this early stage rumours were entertained, but equally shot down – two friends going out together without the relationship rumours circling? Of course not.

But the plot thickens, there was in fact more to the story; at the time the pair first stepped out together, Cara Delevingne was rumoured to be in a relationship with Paris Jackson.

Cara Delevingne and Ashley

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3rd May 2018: First Social Media Selfie

But this didn’t stop the girls adding fuel to the fire when they posted a cosy selfie just a few days after their first public appearance. Although there may not have been anything entirely suggestive about the image, Cara’s bisexual nature inevitably resulted in many accusations on the pair’s relationship.

She has openly revealed and acknowledged her sexual preferences on many occasions:

“Films and fantasy and books were so incredible to me and I learned so many lessons from that. That was why I never wanted to accept my sexuality. Disney princesses all love men and that’s the way it is. And I’m not going to be a princess if I don’t like men.”

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Were they friends? Was Ashley also bisexual? Were they more than friends?! Fans were – naturally – sent into a frenzy.

27th May 2018: First Public Display Of Affection

Hanging of the neck of a ‘friend’ doesn’t exactly scream friend zone – never mind a kiss on the neck whilst hugging said friend from behind; the infamous ‘parking lot’ picture finally suggested the ‘rumours’ were in fact not rumours and Paris was indeed old news.

Cara and Ashley hugging in a Parking Lot

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28th July 2018: Caught On Dancer Tati McQuay’s Instagram Story Together

Still avoiding inundating one another’s Social Media profiles with pictures of each another, and not being caught out in public together for more than 2 weeks – the girls intentionally/unintentionally created a further air of mystery around their ‘relationship’; that is until the pair are caught on the Instagram story of dancer Tati McQuay, further peaking the interest of fans.

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8th August 2018: West Hollywood Coffee Run

Fast forward to August where the pair are spotted out grabbing a coffee in West Hollywood – unfortunately the most exciting aspect of this paparazzi picture was the jazzy socks Miss Cara Delevingne donned; the sign of a happy relationship – willingly wearing silly socks with your other half out in public? We think so. She told Elle:

Cara and Ashley getting coffee in West Hollywood


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“Sometimes I’m the most awkward person in the world in my body and my skin. Sometimes I’m far too confident. I think it’s a constant journey.”

8th August 2018: Cara’s Initials Spotted On Ashley’s Necklace

What may appear as an innocent and sultry selfie from the blonde bombshell, caused frenzy amongst fans – why? Yep, the necklace. Forget ‘tramp stamp’ tattoos, jewellery with your other half’s initials on are the latest trend (just ask Kim Kardashian).


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Ashley donned an ‘A’ and ‘C’ necklace – just to reiterate the fact that the pair are joined at the hip. Couple. Goals.

12th August 2018: Cara’s 26th Birthday Party

In the same month, we saw Cara turn 26; and what would a birthday party be without all of your nearest and dearest, friends and family and other half? Well fear not, Ashley was of course right by her Mrs’ side as she celebrated turning 26.

And what makes this picture even cuter? The fact Ashley is not literally by Cara’s side, showing just a couple months in and she is already well immersed and integrated into the trendy circle of Cara Delevingne.


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16th August 2018: First Public Kiss

And here we have it – what we’ve all been questioning – what we’ve all wanted confirming – what we’ve all (secretly) wanted to see – THE KISS.

Cara and Ashley first kiss

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Finally, Ashley and Cara put the rumours to bed and embrace their blatant obsession with one another: the public kiss in Heathrow Airport. The pair look incredibly relaxed and at ease with one another and certainly shut down those ‘just friends’ rumours for good.

Although the friendship rumours are indirectly shot down, the girls STILL don’t publicly admit they are in a relationship. Give it up girls.

9th September 2018: The Pair Attend Toronto Film Festival Together

Couples who slay together, stay together. The girls definitely slayed at the Toronto Film Festival, but body language expert Patti Wood claims the girls look less than loved up in the image below:

Cara and Ashley at Toronto Film Festival

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“We don’t see any emotion from the couple that would indicate they’re happy together.”

29th September 2018: Ashley Supports Cara During Paris Fashion Week

The week every model looks forward to: Paris Fashion Week. And what would one of the biggest weeks in your year be without having your other half by your side supporting you?

Ashley evidently thought the same, as she was sat front row at the Balmain show that Cara opened. And as if the couple couldn’t be any more smitten– they immersed from the Fashion Show together with matching sleek hairstyles. What bae does, I do.

Cara and Ashley at Paris Fashion Week

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Here we see Cara stepping into protective mode, as she appears to be shielding Ashley from the crowds and paps. Interestingly enough, Cara stated:

“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. So it’s weird.”

She definitely appears to be wearing the trousers in this relationship – which leads to the end all question: who wore the trousers in her relationship with One Direction heart throb Harry Styles?

4th January 2019: Ashley Is Caught Grabbing Cara’s Behind In The Maldives

Fast forward to January and the girls are still going strong – and this rather raunchy picture is captured of the pair whilst on a trip to the Maldives. Ashley just cannot keep her hands to herself – ‘friends?’, we think not.

It appears it’s not just Cara that’s got a ‘cheeky’ side, after she revealed the following:

Cara grabs Ashley's bum in the Maldives

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“I’m very good at giving love and not at receiving it.

“I’m the same in bed. I find it quite difficult to receive pleasure and love and things like that, so I love to give.”

-Cara Delevingne

5th March 2019: Ashley Meets The Delevingne Family

The inevitable step in any relationship: meeting the family. The the girls recently took the next step in their relationship when Ashley shared this picture on her Instagram, alongside Poppy Delevingne – Cara’s elder sister.


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6th March 2019: Ashley Sits Front Row At The Chanel Fashion Show Cara Opens

What would a Chanel show be without Cara Delevingne? Delevingne opened for the iconic Chanel Spring/Summer Fashion Show, in remembrance of the late Karl Lagerfeld and Ashley was there waiting after the star studded show for a ‘post-show cuddle puddle’, captured by Cara’s stylist Jamie Mizrahi.


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post show cuddle puddle 👩‍❤️‍👩 @chanelofficial

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10 months later and the girls don’t seem to be showing any signs of cooling off from one another any time soon. A US Weekly source, close to Ashley, revealed the following:

“This is the first girl she’s ever dated. This relationship with Cara is the first time she’s been in a healthy relationship, and she feels as if it’s really easy with her.”

And so the Cara Delevingne envy continues…

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