Caroline Calloway

In January 2020, Calloway announced that she would be writing two books. The first of these books, Scammer, was to be printed on demand on April 1, 2020 and has since been delayed. Calloway claims that her next book, And We Were Like, documenting her time at Cambridge University, is planned for winter 2020 despite her original publisher never confirming her book deal was back on.

In April 2020, Calloway posted a nude photo of herself on her Twitter account as a "humble apology" to the first part of her essay, I Am Caroline Calloway. She later announced her OnlyFans account. When she posted her projected income from the platform, online sex workers criticized her for her privilege in being able to use her existing fame and her condescension towards them.

During her senior year at Cambridge, Calloway hired Beach to co-write a book proposal and memoir about Calloway's life. Calloway's literary agent was Byrd Leavell. Leavell has since commented on his experience working with Calloway, stating that she was "deeply unwell, deeply dishonest" and that "It was more important to her to be seen as an author than it was to be an author. She didn’t know how to be an author." Calloway announced via her Instagram stories in 2017 that she was withdrawing from her book deal after failing to fulfill her contract.

In 2019, Natalie Beach wrote an essay for The Cut, "I Was Caroline Calloway", chronicling her toxic friendship and collaborations with Calloway. In 2020, Calloway responded to Beach through her self-published website, "I Am Caroline Calloway".

In August 2019, Calloway hosted a creativity workshop at an event space in the East Village. Although she specified that press was not invited to the event, a reporter from Vice attended and published an article about her experience, exposing how little the attendees received in return for the price of a ticket.

In December 2018, Calloway launched an international "Creativity Workshop Tour," only for it to be quickly recognized as a scam. This tour was cancelled due to Calloway failing to book venues despite already selling $165 tickets to these events. Eventually, Calloway held two events in New York. Scottish reporter Kayleigh Donaldson created a twitter thread exposing Calloway as a scammer, which garnered news coverage comparing Calloway's tour to Fyre Festival.

Calloway's early Instagram captions chronicled her relationship with her boyfriend, but the two split up in 2016. Since that break-up she has continued to narrate details about her love life on Instagram, but has started covering faces with a blue butterfly to obscure identity.

Calloway spent her freshman and sophomore years of high school at the all-boarding Episcopal High School in Alexandria, Virginia. She spent her junior year in Viterbo, Italy with SYA. Calloway spent her senior year of high school at Phillips Exeter Academy. Calloway was an intern at the Metropolitan Museum of Art in 2012. She described herself as "their worst intern ever." Calloway attended New York University for several years before dropping out. In 2013, she enrolled at Cambridge University after being rejected twice.

Calloway joined Instagram in 2012 and experimented with growing her following with Natalie Beach, another student at NYU. Calloway initially bought followers to grow her account. According to Beach, she ghostwrote the image captions for Calloway's audience.