Cambridge's Most Controversial Instagram Celebrity Gets the Last Laugh

American Caroline Calloway has turned her adventures at Cambridge University into an elaborate Instagram narrative, which is being turned into a memoir.

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Sep 2 2015, 6:15pm

Image via Caroline Calloway

Perhaps the most important thing to remember about Caroline Calloway is that she is in college. Having once been in college myself, I feel guilty bringing this up; I can remember very well the frustration of being essentially patted on the head when I complained about exam stresses or anticipated my term abroad. (London.)

Calloway is a 23-year-old Instagram blogger who uses the social network to document her experience as an American undergraduate at Cambridge University in the UK. Presented (in her Instagram bio) as the "Story of my life. Literally.", Calloway's "blog" is either a conscious experiment with narrative and form or a natural progression of literary history, now available online. Or it's some combination of the two. Like much of the millennial-tinged content on Instagram, Calloway's posts are bright and aspirational, sometimes augmented with cute drawings or text, and often fuzzy around the edges, lending them the fantastical look of dreams or fairy tales. Compounding this effect is the fact that they also frequently star her good-looking Swedish boyfriend, Oscar, or the good-looking buildings that dot the tourist attraction that is the Cambridge campus.

What sets Calloway's blog apart from the network's 300 million active accounts is that she is doing whatever she's doing with some amount of intention; her captions are paragraphs long, often reaching the Instagram's limit ("about three paragraphs in a Microsoft Word document in 14 font"; she doesn't know the exact character count), and they craft a cohesive narrative. What sets Calloway's blog apart from your standard "My Glamorous and Exciting Life Abroad" write-home-about is that she's doing whatever she's doing on Instagram and, although she has begun to "play with jumping around in time," the narrative is about a year behind that of Calloway's actual life. She has over 419,000 followers and a legendary literary agent, Byrd Leavell, whose clients include other wildly read writers with non-traditional trajectories, like Babe Walker, Tucker Max, and former Maxim editor Justin Halpern, who wrote Sh*t My Dad Says."

Calloway's story sounds like a classic book deal narrative, in which the print world cottons on to a social media success story and showers its starry-eyed creator with a huge advance. Indeed, to read the Daily Mail article that began getting Calloway attention from the non-Instagram realm, you would think she, too, was trying to do something very deliberate if you're generous; the article declares that the student's "fairytale life" is enchanting Instagram with endless and "carefree" stories of "spires, black-tie balls and Champagne on the river."

I think it would be hard to find an American who, during their first week at Cambridge, didn't genuinely feel like it was fairy tale.

But meeting Calloway—a self-describedly "chatty" hair twirler who talks fast and nervously, often forgetting the question she was answering and vacillating between exuberance and self-doubt ("I'm probably revealing myself to be the world's largest narcissist," she demurs when talking about how much joy her fan letters bring her)—reveals her to be much more normal than that story would suggest. Which is perhaps why the aspirational aspect of Instagram looks so good on her.

"I think it would be hard to find an American who, during their first week at Cambridge didn't genuinely feel like it was fairy tale," she says, referring to the notion brought up by the Daily Mail piece. But she maintains that @carolinecalloway is a blog "about relationships." "A lot of people think I hang around Cambridge as this Hogwarts-obsessed Anglophile looking for anyone with a British accent," she says, speaking with a lilting enunciation that some would denounce as poseur-y Anglophilia but actually probably can't be helped. "I do love Harry Potter, and I do love British accents, but neither of those things are what my blog is about or what I want to [be] as a writer."

Indeed, what she wants to be as a writer is the real priority for her. Calloway was born in the DC suburbs, spent her junior year of high school abroad in Italy, and then graduated from Phillips Exeter, the boarding school in New Hampshire. After "being rejected multiple times from basically every Ivy League school under the sun," Calloway spent a year and a half at NYU and set about writing a book immediately.

Or trying to, at least. "I was having lots misguided attempts at coffee with people who were actually in the publishing industry doing important things with their lives," she says. "Basically they were like, if you're a first time author, it doesn't matter how good your proposal is or how good your literary agent is. You just have to have the statistics or data to prove that people will buy your book. And as of that time I didn't even have numbers that would prove my own mother would buy my book. So I saw so many fashion bloggers succeeding on Instagram...but I hated being a fashion blogger." The important publishing industry people gave the then-teenager the advice they give to most teenagers: You have to have something to write about before you can be a writer.

That was about four years ago. She applied to transfer to Cambridge during her sophomore year and was accepted to study at St. Edmund's College, which she says is "objectively the worst"; it's one of four colleges at Cambridge designated for "mature students," and most of its population is pursuing a graduate or doctorate degree, though they do accept undergraduates younger than 21, which is how Calloway ended up there. She has already begun blogging very sporadically, using the hashtag #adventuregrams, to try and generate a following, and at some point, something clicked—the fairy tale thing likely helped. "What was so comforting was that the more I started being honest on my blog, the more people responded."

What Calloway is doing doesn't classify as study abroad, since she's enrolled in Cambridge in a full-time undergraduate program and not a visiting student whose experience is limited to friendships with other visiting students and boozing in quirky locales (though she does mention illegally drinking champagne on the roof). Nevertheless, we live in a time when many know the angry exhaustion of being kept up all night by partying Australians in a communal hostel bedroom—a time when it is common to have one's view of significant cultural and historical monuments obstructed by bright purple NYU t-shirts and tour-guide umbrellas bobbing through a crowd—the practice of pursuing university education abroad has earned a bad rap.

To openly fantasize about the "fairy tale" (Calloway's word) of studying at a Hogwartsian institution where everyone's accent is pleasant is, as they would say in Cambridge, pretty cringe. Calloway seems simultaneously aware of this and aware of the fact that she succumbs to it, just as she is aware that regularly racking up over 12,000 likes on Instagram is both not enough and incredibly rewarding. She says she writes a year behind because she can't produce work fast or enough or with enough distance to "not try to make [her]self be the hero of every situation.

Calloway also says the Instagram was always in service of the book deal, and not the other way around. She refers to herself as a "memoirist" as often as she does a "blogger" and cites as influences Sloane Crosley, David Sedaris, Lena Dunham, and David Foster Wallace. (Re: Dunham: "There's so much jealousy. She's so brilliant; I wish I was a better person to love her with my whole heart.") These authors are displayed on her bookshelves, as well as the Yale Book of Quotations, The Aeneid, and some Locke, Aquinas, and Spinoza. She really is in college! When I ask about her grades, she gets uncomfortable. "This is the moment when you're supposed to have a publicist," she says. "Because it could be a totally normal thing to answer; they weren't terrible. But they weren't great either, so I don't know. I didn't get a third, which is the worst. I got a second class." I tell her that's fine! and she says, "I can already see a situation where my boss is going to be mad at me for talking about my grades."

Although at one point her website promised the essay collection would be available in January 2016, now Leavell says they will submit the book proposal to interested publishers ("a long list," according to Leavell) this fall. This means the book—which, according to the only photo on Calloway's site, will sport a very bright teal cover and be titled And We Were Like—won't be available for awhile, though the plan, according to Calloway, is for it to come out next summer, after she graduates from Cambridge. "Hopefully," she says, "it will be good enough to write a second."

In typical college student fashion, she procrastinated on the proposal so much that Leavell had to designate specific hours during which she would come into his office and work, monitored. When I ask if she has a blogging schedule, to take advantage of peak Instagram traffic times or just to grow her following, she replies, "No. No, no, no, no. Maybe if I was just better at being a functioning human. Sometimes I feel like, if I don't post, I'm letting [my readers] down. I get such bad anxiety if I really let it go too far." During this past term—when she was very worried she would fail, "in the same paranoid way as anyone who thinks they're at a college where every single person there is more qualified to be there"—she didn't post for a few months. She returned with a post that acknowledged it; under a photo of a smiling, succinctly dressed blogger on a laptop is a caption in the same consciously narrative tone that characterizes the entire account:

People ask me all the time how I balance running a blog and going to college and the answer is I don't. Either I'm bumming around ancient coffee shops with my laptop while my friends are in the library, failing out of Cambridge one Instagram caption at a time. Or I'm living in radio silence, meeting my essay deadlines, professors for coffee, parents' expectations. There is no in-between.

The only bad comments she says she gets are on articles that people have written about her—particularly in the Cambridge tabloid, the comment section of which she describes as "by far the meanest place ever." "The few times I've let myself read the comments on those [other] articles, I've had to turn to the comments section of my own Instagram as, like, chicken soup for the Instagram soul," she says. It's kind of sad.

Instagram fame is strange, we agree; it involves a notoriety that exists in a bubble (a word also used to describe universities like Cambridge and the Ivies). "I don't think it's a type of fame," Calloway says, for that reason. Although she's been recognized in the street once or twice, she was "more delighted by the experience than the person who [was] recognizing me."

At pubs around Cambridge, she'll occasionally get called "the Instagram girl!" in a drunken 1 AM haze, but in those kinds of situations, she is much more likely to flee than to excitedly ask the person if they really like her writing. Although her fans are very supportive, the Cambridge community as a whole seems less so. "I would never say people are hostile, but people are a little condescending about [the blog] sometimes," she says.

Her professors, for the record, "could not be less pleased" with the attention her project has gotten. "There are only about 23 people each year from around the world who get accepted into the undergrad history of art program, and I could say with pretty much one hundred percent certainty that no one's thrilled that I'll be the first one to be a professional Instagram blogger with my degree," Calloway says. "Like whenever they talk about Caravaggio's use of chiaroscuro or the use of contrapposto marble sculpture, I'm sure they would hate to know [they're] being used to filter Instagram pictures."

Like being introduced as a "college student," being labeled an "Instagram blogger" is a double-edged sword: It comes with a lot of perks and privileges, but it's hard to be taken seriously, partially because of those perks and privileges. Especially at a place like Cambridge, Calloway finds it difficult to deal with this tension. "I feel like the more serious a life event is that you share on social media, the more ridiculous it sort of becomes, the more you sort of self-trivialize," Calloway says. "If you post something describing your breakup and what just happened, [for example], it makes the event a type of millennial pageantry that detracts from what the experience must be for you."

For writers, social media is becoming a necessary tool to gain readers. But whenever it has to compete with the gravitas of print, the internetty stuff seems petty and insignificant by comparison. With her blog, Calloway is but one of many people both instigating a shift away from this dichotomy and simply going along for the historical ride of it. While some have declared that Calloway is "inventing the Instagram memoir"—and while her project does seem much fresher and authentic than, for example, #Twitterfiction, which is usually very "cringe" in its heavy-handed dedication to "storytelling" over story—what she's doing ultimately sounds like something that would have happened in any number of ways, a "trend" with origins it would be impossible to pinpoint.

I could say with pretty much 100 percent certainty that no one's thrilled that I'll be the first professional Instagram blogger with my degree.

"There are so many paradigms we subscribe to on Instagram without even realizing it," Calloway says. "It has to be in present tense, and it has to be smart and witty and short and spontaneous. It has to be something that we throw away tomorrow or even half an hour after it's posted. [But] it doesn't have to be any of those things. It can be something meaningful for a wide audience, something that's meant to be read a year from now. If you ask someone, 'Do you want a lot of followers?' and they're like yes, they seem like such a shallow person. But if you ask a writer, 'Do you want a lot of readers?' and the writer says yes, it would be like, of course you do, that's why you want to be a writer."

There are less weighty implications of this life, too, of course. "I'll get asked if I'm 'going to put this up on my blog' every time I take a photo in a group situation," she says. "I take out my camera, and everyone sort of slightly freezes, and I have to shout things like, 'Be natural! Yes, gorgeous, gorgeous! Absolutely! You look fantastic!'"