Caroline Calloway: a Cautionary Tale in Self-awareness
Caroline Calloway is “sexy and sexual and grief-stricken and shrewd and zany and romantic and generous and imaginative and manipulative and reckless and ambitious and good,” according to her Instagram. She is a writer, an artist, an art historian, an accused-scammer, a refuter of the title, and the author of an unpublished book titled, SCAMMER. Clearly unafraid of contradiction, Calloway is someone who uses her perpetual Instagram presence to promote radical online honesty which includes incessant documentation of a lifestyle that is largely unattainable for the majority of her followers. She claims to be progressive and supportive of marginalized communities, but she promotes eurocentric beauty standards, and has often denied her class privilege. She is unapologetically attention-seeking, and extremely self-involved, but deeply and almost shockingly lacking in self-awareness. Caroline Calloway is a cautionary tale.
Scrolling through her Instagram, it can be difficult to tell when Calloway is being honest or performative. It’s unclear if some posts are earnest or snarky, serious or playful. Calloway, who has had a long and drawn-out rise to internet stardom, has evolved her platform to serve her needs. Originally, she was a pretty, white, clever American girl who both studied and partied in castles in Cambridge, and who rose to Instagram fame for her long, detail-heavy captions about her life abroad. Later, she returned to America and told the truth about Cambridge: she was addicted to Adderall, she nearly failed to graduate, and she had lost her book deal. Her truth was a truth abridged. She transformed her persona into that of the lost, dejected, anxious, and recovering 20-something (who lived, job-less, in a West Village studio).
In December of 2018, Calloway began advertising $165 “creativity workshops” marketed toward her followers, which ultimately failed, went viral, and granted her the title of “scammer.” Calloway spent some time fighting the title before leaning into it, even adding it to her Instagram bio, and selling baseball caps. Calloway used the criticism she faced online to garner sympathy and attention. She launched herself into a new online aesthetic: that of the snarky, dogged, millennial victim hellbent on making her fame work for her.
In September of 2019, Natalie Beach, Calloway’s ex-friend and apparent ghostwriter published a (somewhat boring, mostly self-pitying) essay in The Cut revealing that she wrote many of the Instagram captions that launched Calloway to fame (which Calloway denies). Several days later, Calloway received news that her father had died, from what was later revealed to be suicide. Calloway’s brand took another turn: in the wake of her father’s death she was loud, outspoken, and willing to talk to whoever would listen. She refused to grieve “normally,” and she consistently began publishing posts that swung from serious to ridiculous, sometimes in the same breath.
Calloway has been compared to Anna Delvey, Billy McFarland, and Elizabeth Holmes, but the scammer aspect of her brand is not what’s most interesting about her. Calloway is more comparable to Lauren Duca, or Lena Dunham, the former of which she had dinner with recently, and the latter having been cited as one of her inspirations. What these women have in common is not merely their fame, or their whiteness, or their privilege. Rather, the three women share an extreme lack of self-awareness, which pairs well with their collective self-delusion and self-aggrandizement. They’ve built brands that are inherently and inextricably linked to the self. Because of this, the three women share a divine gracelessness when it comes to criticism, which they often face. Dunham and Duca have both been the subjects of critical, careful profiles, during which they notably attempted to control the narrative being written about them. They are quintessential “white feminists,” women who exist in a self-made paradox of being extremely privileged and unwilling to admit their privilege.
This is what’s dangerous about Caroline Calloway. Like her friends, her role models, and white feminists everywhere, she cannot and will not be held accountable for her actions. She has consistently exploited her followers, turning them against her critics, and profiting off of them (via pre-sales of SCAMMER or by selling them shoddy paper cut outs for anywhere from $100 to $400. She has dismissed her class privilege, sharing photos of her father’s home in the hope of gaining sympathy from her followers. She willfully sells her lifestyle to her followers — many of whom will never come close to attaining the economic luxury of going to pilates, and then spin, then sauna, and then pilates again, just for fun, day after day. Even when Calloway has used her platform to support marginalized communities, she’s still made it about her. She’s spent so long writing her story, she’s unwilling to consider that its heroine might actually be more of a villain.
But here’s the thing: denying the damage you have caused and the privilege you’ve been granted erases neither the damage nor the privilege. Calloway will continue to sell herself, her brand, and her lifestyle. She will continue to claim victimhood. She will continue to exist as an illustration of white-woman privilege — one that refutes criticism. She will continue to be (or claim to be) “sexy and sexual and grief-stricken and shrewd and zany and romantic and generous and imaginative and manipulative and reckless and ambitious and good.” She will continue to be a symbol of white privilege, but even more so, a lesson in self-awareness.
Maybe Caroline Calloway is a scammer, but who cares? More than anything, she’s an example of what not to do. We live in an age in which we’re constantly online, and many of us (myself included), have the privilege and the power to shape the online communities that we’re involved with. If we’re not careful, our brands, our aesthetics, and our online personas can get ahead of us — shaping us, instead of the other way around. What results is a loss of self: our online personas become indistinguishable from who we actually are. It’s too late for Caroline Calloway. We have to try to know the difference.
About the Author
Megan Burns (she/her) is a social researcher at New York University mainly interested in identity, morality, and policy. An observer by nature, both her personal and professional work is largely inspired by the people around her. When she's not writing (which is often) she enjoys art galleries, reading short stories (or long stories), shirley temples, dancing, and collecting knick-knacks.
