Ashley Benson knows her way around a secret, but could she keep it? As it turns out, the Pretty Little Liars star managed to remain tight-lipped about her romance with model and actress Cara Delevingne for an entire year. Let’s be honest though: fans knew exactly what was going on (with or without the matching tattoos as confirmation). Benson fans are well-versed in a mystery.
The pair first sparked romance rumors after leaving Kylie Jenner’s 21st birthday party in August 2018. Then, they were snapped kissing in Heathrow Airport, and before long, they were dangling clues about their love life in front of the tabloids like a deleted scene from the very show that made Benson a household name. The next year would see Benson and Delevingne travel across the United States, Europe, and the UK while fielding both breakup and marriage rumors, and generally just being happy.
Considering the couple only confirmed their relationship during Pride Month (June) 2019, before reportedly calling it quits in April 2020, there’s a lot most of us didn’t know about their whirlwind romance. Let’s dive into it.
Ashley Benson never dated a woman before Cara Delevingne
Before the pair came clean about their relationship, Ashley Benson and Cara Delevingne reveled in speculation. The couple posted photos of each other to Instagram throughout 2018, but things looked less platonic and more romantic when they were first spotted holding hands at a bowling alley in May of that year, according to Seventeen. Needless to say, this shocked fans, especially considering Benson’s dating history.
According to J-14, the actress had been previously linked to Ryan Good, Justin Bieber’s stylist and an executive producer on Punk’d. The pair had an on-and-off romance that lasted the better part of Pretty Little Liars‘ excessively long and massively complicated run. Seriously, anyone who claims to know what was happening by Season 7 is probably a pretty little liar themselves. Nonetheless, when PLL geared up for its final season in 2016, Benson was onto bigger and better things. According to Playboy, the actress was linked to bisexual PLL co-star Tyler Blackburn, though they never officially dated. After that came Delevingne.
According to Us Weekly, Delevigne was the very first woman Benson ever dated, and their romance also marked the « first time she’s been in a healthy relationship, » proving that sometimes the most unexpected thing is the best possible move.
Ashley Benson’s necklace was a clue to their secret romance
As the months dragged on in Ashley Benson and Cara Delevingne’s undercover romance, the Pretty Little Liars star took a page from the series that made her famous and dropped some serious clues that would give Hanna Marin a run for her money. In August 2018, the actress made headlines for wearing a personalized necklace with the initials « C » and « A. » Of course, what could « C » stand for but Cara? Talk about leaving a breadcrumb trail for curious fans!
That same month, Benson was spotted wearing the dainty, initial necklace while cuddling up to the Victoria Secret model at Heathrow Airport. According to People, there were « multiple smooches » and they exchanged « kisses a number of times » while waiting for a taxi. The strangest part about the whole Heathrow reveal was that Benson was actually spotted « kissing a mystery guy » at Kylie Jenner’s birthday party just days prior, even if Us Weekly claims she ultimately left with Delevingne. Was she trying to throw us off their trail?
Cara Delevingne seemingly confirmed their relationship in a clapback
Before Ashley Benson and Cara Delevingne went public with their romance during Pride Month in June 2019, the British model more or less confirmed their relationship in the comments section of an Ashley Benson fan’s Instagram account that April. Most of us didn’t expect so much drama to go down on an unofficial page (this wasn’t YouTube), but nonetheless, the homophobic social media troll still needed to take a seat.
According to Elle, the troll revealed itself underneath a fan-posted video of the then-happy couple. They claimed Benson needed to « stay away from the devil … I’m sure many strong handsome religious man would take you back in a heartbeat. You’re not like the you aren’t gay you love men and you need one. »
Benson fired back and told the troll to « stop making things up, » but Delevingne was clearly seeing red and took the comments much more to heart. « You are f**king disgusting! If you have a problem with true love then come say this s**t to my face instead pathetically hating through Instagram, » she wrote (via Elle). Wait a minute: Delevingne wrote « true love » underneath a video of her and Benson. And just like that, their romance was considered covertly confirmed.
Ashley Benson and Cara Delevingne reportedly moved in together
Ashley Benson and Cara Delevingne’s romance certainly moved fast — from kissing in a London airport and holding hands in the ocean side paradise of Saint Tropez to making out on Instagram. It seemed like they were making enough romps around the world to rival that time Taylor Swift dated Tom Hiddleston for two seconds. The pair reportedly also reached a huge milestone sometime around the one-year mark: they officially moved in together, according to Us Weekly. Moving in with a partner isn’t a decision to take lightly, but when you’re feeling it, you’re feeling it.
Benson reportedly moved into Delevingne’s house while their relationship was still relatively secretive. According to Variety, the Pretty Little Liars star put her Los Angeles home on the market, which she was hoping to sell for a whopping $2.45 million. This was a huge bump up from the $1.8 million she bought it for a year and a half prior, but she did reportedly spend around $700,000 on renovations.
The fact that Benson sold her home rather than keeping a back-up pad showed that the star had a lot of confidence in her blossoming romance — even though it had only been a year. Then again, when you’re ultra-rich, you can just buy a brand new multi-million dollar home at the first whiff of trouble.
Cara Delevingne and Ashley Benson’s taste in furniture was…interesting
It’s not clear exactly when Ashley Benson moved in with Cara Delevingne, because their relationship had been kept so wildly under wraps, but one thing was clear: they certainly had unique taste in interior design. And we thought a trip to Ikea was just about as exciting as domestic life could get!
According to the Daily Mail, the ladies were snapped by the paps carrying in a saucy bondage bench that would find itself at home in Christian Grey’s mansion. The bench cost a whopping £360 (about $437 USD) and reportedly came with 10 different kinds of restraints. No one knows exactly where the couple purchased the item; however, it probably wasn’t at Target, where they were seen browsing the aisles in domestic bliss earlier that day. The tabloid described the pair as « giggling girlfriends » who « couldn’t keep the smiles off their faces. » Okay, then.
Vice pointed out that the whole thing might have been a PR stunt. As we already know, Delevingne enjoys feeding the trolls, and it wouldn’t be shocking if she wanted to mess with the paparazzi camped outside of her house. We’d be sick of them, too. Whether they were playing a prank or proudly living their best lives, the whole thing was still glorious.
Cara Delevingne and Ashley Benson went public during Pride Month
In June 2019, Cara Delevingne and Ashley Benson finally, finally gave fans what they wanted. They officially confirmed their relationship on the British model’s Instagram account. The star posted a video of herself kissing the Pretty Little Liars actress with the caption « #PRIDE » and some rainbow and heart-eyes emojis. It only took a year of us following their exhausting trail of breadcrumbs. Seriously, Benson learned a little too much from her time hanging around A.
In an interview with E! News at the TrevorLIVE Gala, Delevingne opened up about why she made the decision to publicly confirm her relationship after an entire year. What was the point when everyone already knew anyway? The girls were already living together. « I don’t know 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? » she said. The British model also gave Benson a too-cute shout-out during her speech at the gala. « I also have another very special woman in this room to thank and you know who you are, » Delevingne said (via E! News). « She’s one of the people who help me love myself when I needed it most and I really needed it. »
Ashley Benson helped Cara Delevingne with her intimacy issues
Cara Delevingne is one of those celebs who says some stuff we sometimes wish we could un-hear. When she’s not buying furniture from Christian Grey’s yard sale, the British model is sharing every juicy detail of her sex life. Of course, knowing she was officially dating Ashley Benson at the time gave everything she said a whole new meaning.
In a March 2019 tell-all interview on RuPaul’s What’s the Tee? podcast (via The Sun), Delevingne opened up about her hobbies (« I used to go to clubs, but I’d rather have sex than go out now ») and her struggle with intimacy. « I’m very good at giving love and not at receiving it. I’m the same in bed, » she revealed. « I find it quite difficult to receive pleasure and love and things like that, so I love to give. »
Though Delevingne struggled to let love in, the star did admit that Benson helped her with the process. During her speech at the TrevorLIVE Gala (via E! News) the star hinted that a special lady in the audience (ahem, Benson) « showed me what real love is and how to accept it, which is a lot harder than I thought. »
Cara Delevingne had a different side when she was with Ashley Benson
Cara Delevingne might have just been a different person around Ashley Benson than she was in some of her other relationships. In an interview on RuPaul’s podcast, What’s the Tee? (via The Sun), the model-actress admitted that she has always been submissive in her relationships with men. The bisexual star has been linked to Tulip Fever co-star Jack O’Connell (though nothing was ever confirmed), singer-songwriter Jake Bugg, and possibly even Harry Styles (though the pair might have just been friends).
« That whole courting process of power is very interesting. And it’s a difference with men and women, » Delevingne said. « I’m always very submissive with men. Always. But with women, I’m the opposite. So it’s weird. » In other words: Delevingne probably took charge in her relationship with Benson, or at least she did while trying to win her over. We’re also willing to bet that the couple saw a whole lot more of the couch than they did any new scandalous furniture they might have purchased. « I work a lot! It’s tiring and it [sex] takes energy, » she continued. Sometimes Netflix and chill really does mean chill.
Let the engagement rumors fly
Cara Delevingne and Ashley Benson knew just how to tickle the press. About a year into their relationship, fans started speculating that the couple was actually engaged. According to The Cut, the rumors were ignited when the women took a holiday to Saint Tropez, and were spotted walking hand-in-hand while « wearing matching gold bands on their ring fingers. » Needless to say, die-hard Cashley shippers couldn’t contain their excitement.
Unfortunately, fans shouldn’t be planning their own funerals just yet because the rumors appeared to be completely false. According to The Blast, Benson had been wearing a ring on that finger « for years. » Delevingne was spotted in March wearing a silver band on her wedding finger during a red carpet appearance. Additionally, a source who spoke to Us Weekly claimed the pair were « madly, madly in love » but also not engaged at the time. Perhaps they just liked wearing rings and messing around with the tabloids.
Cara Delevingne and Ashley Benson made their love tattoo official
Cara Delevingne was not a fan of the term « official. » In a June 2019 interview with E! News where the star was asked if she was « Insta-official » with Ashley Benson, the model admitted, « Sure. I don’t know — I don’t like the ‘official’ thing, but you know, it’s a little something. » Strangely enough, the star didn’t seem to have a problem with the official nature of a tattoo, which takes a lot more effort to delete than an Instagram post.
The British model and Pretty Little Liars actress might not have been planning to tie the knot, but they certainly tied themselves together for as long as it takes them to get laser tattoo removal. According to Harper’s Bazaar, the pair got matching tattoos of their initials. Delevingne got an « A » underneath her left breast, which was visible on both the Met Gala red carpet and the red carpet for the TrevorLIVE Gala. Benson revealed her tattoo explicitly in an advertisement for her sunglasses collaboration with Privé Revaux. She got « CD » tattooed on her ribs next to her left breast.
At the time, we just hoped these ladies wouldn’t go the way of Johnny Depp and Winona Ryder. Wino Forever is never a good look.
Cara Delevingne’s pet name for Ashley Benson was super sweet
Just when we thought Cara Delevingne and Ashley Benson couldn’t possibly get any cuter, we learned that the British model had a too cute pet name for her former Pretty Little Liars love. During the Delevingne’s speech at the TrevorLIVE gala (via Yahoo!), the star proudly proclaimed, « I love you, Sprinkles. » Of course, we couldn’t be totally sure she was referring to Benson, but Benson, who was supporting from the audience, posted an Instagram story of the Suicide Squad star from the stage and wrote, « Love you @caradelevingne. Proud of you. » Excuse me, could we have a girlfriend this supportive?
Despite the then-couple’s A-list status — and the fact that they did things like speak at galas and gallivant through Europe — Benson and Delevingne were actually just like everyone else in love. According to a source who spoke to E! News in June 2019, the former celeb pairing did regular couple things « like get coffee, walk the dog or go to the movies. » The insider continued, « They like to stay home together a lot and just chill. They are very sweet and loving together. They are always doing simple nice things for each other and it all comes very easy and naturally. They are committed to one another and very much in love. »
Cara Delevingne seemed ready to tie the knot
The engagement rumors might have been false, but it’s clear Ashley Benson and Cara Delevingne were once ready for a real commitment — one that couldn’t be lasered off and must be negotiated painstakingly through an attorney upon its demise. In just their first year of dating, the pair had already run through a number of major relationship milestones like becoming Instagram official, moving in together, going on a European vacation, getting matching tattoos, and buying a wild BDSM bench. Okay, so this was the millennial version of milestones, but we digress.
After running through all of these major moments, it seemed like Delevingne was looking to settle down. According to Life & Style, the British model implied that she wanted to tie the knot with Benson during the CTAM TCA Summer Press Tour for her Amazon series Carnival Row. When asked if she was ready for a lifelong commitment, Delevingne reportedly replied, « Oh my God, yes. I mean always. Love life. » Were wedding bells really on the horizon for the pair?
After almost two years, Cara Delevingne and Ashley Benson split
Cara Delevingne and Ashley Benson spent their relationship being papped while giggling, but apparently, things weren’t as lighthearted behind the scenes. Last we heard, Benson was ready to settle down, but things have taken a devastating turn. Can someone please tell us why we feel so personally invested in this couple?
According to People, the actresses broke up in April 2020 after nearly two years of dating. « Cara and Ashley always had their ups and down before but it’s over now, » an anonymous source claimed to the magazine. « Their relationship just ran its course. » Meanwhile, another insider cited by Life & Style alleged that breakup wasn’t « surprising » to the former couple’s friends, because they had reportedly been having « problems. » This second source added, « No one wanted it to be true. They were great together — a dynamic duo — and everyone loved having them around. That’s why this is so hard. »
Delevingne’s reportedly been leaning on her friends post-split and hanging out with Rainey Qualley, Margaret Qualley, and Kaia Gerber, per People. Meanwhile, Benson has been bored in the house. At the time of this writing, neither party has confirmed the breakup. What’s going to happen to the tattoos Benson and Delevingne got in each other’s honor? At the very least, it seems like they’re still friends, considering Benson posted a TikTok of Delevingne on Instagram just weeks before their split.