Arriving a day late and in the middle of dinner, the “Gatsby of Cambridge” cut a dishevelled figure. She had missed yesterday’s Eurostar to Paris. “A one-off bender,” she said. To her coursemates gathered around the dinner table, the excuse fell on deaf ears.

Cambridge’s Art History cohort were in France for a five-day residential trip to study Gothic architecture. But with her editor pushing her to complete a book she had no intention of finishing and a crippling adderall addiction to contend with, the internet celebrity had other things on her mind.

Caroline Calloway certainly didn’t apply to Cambridge to top tripos or get a first. She hadn’t even gotten into the University on her own merit. The American forged her school transcript, changing her D+ in Ancient Greek to an A-.

“That class was at the same time Andy had a free period during which he liked to fuck me in his top bunk bed,” she writes in her new book Scammer. “I began by photoshopping my Exeter transcript. Was this difficult with their complex visual watermark? Yes. But I’m an art historian and artist”.

Caroline was at Cambridge to live May Week every week and, while she was at it, build a brand. She chose an Instagram handle, bought 40,000 followers for $4.99, and found an image for herself: orchids in her hair. “She knew what she was doing,” remembers an acquaintance. “And I think it shows. She’s got a big platform”. 

Caroline capitalised on Instagram while the platform was still in its infancy. She was one of the first people to use social media to “influence”. “Instagram in the spring of ’13 was still a photo-sharing app only hip coastal teens used for inside jokes,” she writes. “Actual celebrities didn’t even have instagram accounts yet”.

Pinned on her moodboard in her NYU dorm, she had a photo of Blair Waldorf. Years later, the makers of the Gossip Girl reboot would base their protagonist, Julien Calloway, on Caroline. “A photo of my face was actually thumbtacked to a moodboard in the HBO’s writers’ room”.

Caroline’s niche was the length of her Instagram captions. “So much [of her appeal] was about her writing,” explains one of Caroline’s closest friends. “Not about, like, the influence-y photo opportunities”.

Calloway was Cambridge’s biggest fan, and “she never felt like she was too cool for it,” her friend says. As an American in an ancient English city, she felt like she was experiencing a “magical world”.

April 7th, 2014

“Welcome to Cambridge, Instagram! … It’s time to party like it’s Downton Abbey Seasons 1 through 4, and ain’t nothin - not even WW1 or Lady Mary’s attitude problem - is going to rain on our insta parade… Today begins an exciting new chapter of collegiate adventure sausage, one filled with Harry-Potter-like castles, Jane-Austen-like balls, and very mixed references to pop culture”.

Caroline says this was all an act. “I smartly doubled down on my own Americanism,” she writes in Scammer. “[I] used the British contempt for them as cover”. At NYU, which she dropped out of to study at Cambridge (she said she couldn’t bear the thought of dying with an NYU email address), Caroline turned her non fiction writing class into an exercise in fiction.

This knack for writing - whether fiction, non-fiction, or something in between - meant that by her second year she had a book deal worth half a million pounds.

But it wasn’t the deal that made her famous, rather her failure to follow through. And according to her ex best friend Natalie Beach, it wasn’t the first thing she failed to write. She claims the instagram captions for which Caroline was most known were her own work.

Whether in her New York brownstone at NYU or renting a room at Downing (she was a student at St Edmunds, which she called “the worst college…objectively”), the so-called “Gatsby of Cambridge” never had trouble making friends.

People were drawn to her performance of extravagance. She hosted parties in Trumpington manor houses, ran Cambridge’s first prom and broke into May Balls. As one friend of hers put it, “with Caroline you feel you are kind of caught up in a whirlwind… [she was] eccentric, fun, loud, adventurous”.

But Calloway’s personality was divisive. “I remember at one point she was quite rude,” recalls a former classmate. Over a glass of rosé during the class trip to Paris, she asked Caroline about that infamous book deal. “And she just held up her hand, and was like: ‘not now, I can’t speak right now’... She wasn’t great fun to be around… she wasn’t someone who sought out company”.

“I think maybe… being through everything that she's been through, she keeps her circle small,” explains a close friend of Caroline’s. “And that’s not to say she’s not maintaining friendships”. Although now living across the Atlantic from each other, “we’ve maintained such a nice friendship,” she tells us. “Like, she’s one of my closest friends”. 

Calloway doesn’t deny, though, that meaningful interactions with those around her weren’t exactly her priority. “I was going through a period of my life where I was not interested in human relationships,” she tells us. “I was interested in pills”. 

Caroline writes in her book that “one way of leaving is behaving so badly that you are left, and when I was 24 this was the only kind of leaving that I knew”. This was true. She begged for enough extensions on her book deal to lose it, she treated her best friend-cum-ghostwriter so badly she wrote a tell-all in The Cut, and she took enough Adderall to almost fail her Cambridge degree.

She wasn’t looking after herself, and the people around her began to realise. “She didn’t bring a spare change of clothes,” remembers Caroline’s classmate of their trip to Paris. “She stank by the end… and she had a hacking cough…I do think she [had] some issues with hygiene and keeping on top of self-care”.

“She was very distracted… she was on her phone with the editor all the time”. Even when off the phone, Caroline was never really present. As the group toured a Gothic Cathedral in Paris, she lit up a cigarette she found in her pocket. It was quickly apparent it was a spliff. 

Caroline still has a scar from the trip. “I put [the joint] out on my fucking hand,” she tells us, waving her wrist at the camera over Zoom, “because, like, my body was so numb, and I was so detached from it”.

She wasn’t just detached from her body, but from her work. “She wasn’t engaged in the discipline at all,” says the former classmate. “She was constantly being frightened to be kicked out”. The revelation that Caroline had never earned the place she applied three separate times to get came as a relief.

“I was actually really relieved when I saw that confession, because I always felt like with our discipline, there’s a tendency for people to think that it’s for posh, idiot, girls anyway”. She did come to classes, though, and one friend remembers their time together at Cambridge far more simply: “We were just living, like, the normal student life”.

Because Caroline was normal. And that’s what she hated most about herself. Or at least, what she most wanted to change about her character. “Upper middle class girls like me were just supposed to pretend to be grateful we didn’t have it worse,” she writes in Scammer. “I had a lot of shame around the fact that I was well-off, but wanted to be well-offer”.

She indulged her status as both an ‘insider’ and ‘outsider’ to mask this normality - a painful reality for a girl who once asked her mother: “What will I be famous for?”. She spent her summers at her boyfriend’s fjord-side getaway in Sweden, but at the same time, fell into step with a group of townies in Cambridge.

“She invited some friends over from America to go to some May Balls, but they forgot to get tickets,” remembers one townie. “She enlisted our help to go to the balls”. The group snuck into Sidney May Ball, and the following morning, found each other again outside John’s. They rented a punt and took it down to Coe Fen. Lying there, on the bank, they fell asleep, later waking up to a gaggle of tourists taking pictures.

“It was the best week of my life,” he remembers. But Caroline could not separate those May Week memories - of changing heels for flats at 3am and frayed hems of floor length dresses - from the realisation that her life was beginning to spiral out of control. Debt newly acquired, she had hit what she tells us was “rock bottom” of her addiction.

“She was kind of living in this rolling ball of adventure,” her townie friend explains. “And I think when you do that for a long period of time, maybe somebody will catch up”. And with her book still unwritten, her agent inevitably did.

Caroline’s health had already been deteriorating, and over the Christmas break of 2016 “she sank into a swamp of solitude and sadness”. She was medicating with sleeping pills: first organic, then over the counter, and finally prescribed.

“I wasn’t trying to die necessarily. I didn’t want to be awake unless I was experiencing that rapturous, vertiginous, quivering amphetamine thrill”. Yet even the thrill became damaging. She had a rule: she could go two nights without sleep, but not a third. She began to break it more often than not.

On the third night without sleep, the tips of her fingers would begin to numb and then her whole hand would go cold. The loss of circulation would spread until she got into a scalding hot bath, which she would drop anything to do.

“I believe people when they talk about their lived experience,” writes Caroline. “I just wished some of them would do the same for me about mine”.

But people did believe her. “She portrays her time in Cambridge as if it was her against the system,” says the classmate. “And the reality is that like the lecturers or supervisors…put in so much effort and so much goodwill to try and help her, and like, get her through that. I guess we gave her the benefit of the doubt. And she actually was just there for the kicks”.

Calloway disagrees. “Trying to characterise the faculty themselves as wanting to help me is so untrue,” she tells us. Put on academic probation in her second year, she felt criticised, and observed. It was only once she stopped asking for help that she was let off probation.

“In a strange way, once I got to the point in my addiction, where I was like, ‘I don’t want help, I want more pills, just leave me alone with my pills,’ It was then that they took me off of academic probation,” she remembers, “even though, like, my academic performance had remained relatively stable throughout this whole time”.

The classmate recalls one conversation with Caroline during which she expressed her incredulity at being confronted by her director of studies about her alleged drug addiction. “And, at the time, she was like: “How outrageous that he’s accused me of being on drugs. It’s so unfair and so prejudiced”.

Caroline remembers feeling “indignant”. Accused not of adderall addiction, but of posting about smoking weed, she was offended to be confronted over something she had “just never done”. “It was really hard to see my Director of studies,” she says, “who is supposed to be your advocate, your closest advisor... jump to conclusions about me”.

But at the time, anything that happened to Caroline could be flattened into an Instagram caption:

“The other week the Head of the History of Art department asked my Director of Studies if I was “on drugs” (True story). “No, that’s just her personality,” she replied wearily. “Caroline always smiles like that”. I wish I could say this conversation was rock-bottom of my Cambridge career, but the truth is that I’ve been exhausting British people with my face since the day I arrived”

Caroline glamorised her life online, but it was clear to those around her that she was suffering. “I don’t think she was always having that much fun,” says the classmate. “She probably was drunk most of the time or high”. Her early captions were nothing but innocent vignettes of an idealised version of her Cambridge life:

July 19th, 2014

“As dusk gathered on the riverbanks I found out that Oscar was twenty-three, about to start his final year at Cambridge and, ‘in a perfect position to look after a fresher like yourself, Miss Calloway’.

‘I’m not a child,’ I said crossly. “No,” he grinned.

‘You’re a fresher. Even harder to clean up after and impossible to control’”.

But as much as Caroline glamourised her own life, she glamourised her own descent into addiction and suicidal ideation too. She is self-aware, perhaps dangerously so:

“But this narrator’s getting older! Wiser! More reliable and eager to talk about prescription pills! And so I want to jump way, way back to my first week at Cambridge… My next photo won’t be a selfie of me melting heroin in a spoon…Or will it? I guess we’ll all just have to keep reading to find out”.

Because as long as you continue to read, the persona of Caroline Calloway (not, in fact, her real name) can continue to exist. The woman underneath - troubled and lonely, but capable of writing darkly incisive prose - still has something to live for. Because for Caroline it’s only worth living if it’s worth writing about. “I’m finally ready to tell you about the life I lived only so that I could one day write about it,” she shares in Scammer. And doesn’t she do it well.

Can you trust a word she says? Maybe not. But it’s a damn good read.

Scammer, by Caroline Calloway, is available for pre-order - for $65.

Article updated 30/06/23