Caroline Calloway Just Wanted To Make Orchid Crowns For Her Friends

In 2009, Caroline Calloway started building the world’s biggest friend group. In January 2019, she wanted them all to finally meet.

“I pride myself on being a very loving, very caring, very non-scamming friend. Like I’m not the friend most likely to scam you,” Calloway told Refinery29 on a phone call a few days after the internet had turned on her. “I'm the friend most likely to bring you a flower you didn't ask for.”

Of her 830,000 Instagram followers, Calloway figured at least 45 of them would want to hang out with her at a loft space in the Williamsburg neighborhood of Brooklyn. There, she’d talk about her journey as an Instagram influencer (more on that later) and answer any questions attendees had about the life she’s famously so candid about on the platform. For $165, she promised to bring to life the hallmarks of her Instagram presence (sitting on the floor because her tiny West Village studio doesn’t have much furniture, exclusively eating salad, and making care packages for unsuspecting friends) to the community that followed it. It was not meant for people who didn’t already “get” it — but they found out anyways, and it turned into what most viral things on the internet do: a shitstorm that nobody can control.

I had been following Calloway since 2015, back when her claim to fame was not Mason jars and salad, but a book deal. The now-27-year-old wooed the majority of her followers by aggressively documenting her picture-perfect education as an American at Cambridge University. She confirmed people’s whimsical fantasies of life in England with a never-ending stream of images of castles and balls and boys. Her lengthy captions, some of which have been preserved on her Instagram account (Calloway deleted many of her posts and has since transitioned to being an Instagram Stories-only account) were a novelty on the platform at the time, and successfully served her larger goal of landing a book deal. Not long after graduating, she pulled out of the book deal, which is its own lengthy story, before settling in New York City and beginning to document her new brand of radical — but aesthetically pleasing — vulnerability.

Writer Kayleigh Donaldson easily began recapping Calloway’s workshop plans, which Calloway adamantly shared every step of on her Instagram Stories, on Twitter.

“That Instagram influencer I occasionally check in on because she's The Worst is now charging $165 for a 4 hour ‘seminar’ on how to be yourself,” Donaldson wrote on December 20 of last year. However, her thread didn’t pick up steam until January 13, when this happened:

“The first event went so well, according to Her, that she's decided to use this as an excuse to not go to Boston or Philly & instead make those people who have already bought tickets come to New York!”

From there things spiraled. Calloway walked back the event’s promises of home-cooked lunch (read: salad), handmade orchid crowns, and elaborate care packages. As Calloway realized and communicated in real time that she was in over her head and did not have the proper experience or resources to plan a tour of this magnitude by herself, it was no longer just her fans who were watching. The rest of the world had picked up on the thread, reaching big names like Seth Rogan and Roxane Gay. But Calloway didn’t realize just how bad it had gotten until she checked her phone at lunch during her tour stop in D.C..

“There were, you know, maybe like 30, 40 comments on my most recent photo,” she plaintively recalled. Comments like “People are talking trash about you on Twitter;” “‘Like’ if Twitter brought you here;” and “Oh my God, she’s being taken apart on Twitter, laughing face, laughing face, laughing face.”

“They weren't just content to mock me on Twitter,” Calloway continued. “They wanted me to be a part of that mocking and to see it.”

Things only escalated. While she was transparent with workshop attendees that she had been made aware of the Twitter thread and that she was experiencing some harassment, Calloway continued the rest of the event before heading home to her mother’s house in the area. In the next few days, she received so many insults, death threats, and media coverage that she called off the tour.

“It is such a true testament to internet cancel culture and the extreme feelings of worthlessness and shame that it can inflict with its razor beam of focus onto an individual that I would have said anything to make it go away,” Calloway said. “I would have been like, ‘I am a scammer. Please just stop,’ if I had felt like saying that would have done anything to make people stop accusing me of something I didn't do, I would have said it at that time because I'd never been through something like this before.”

Even her decision not to write her book, And We Were Like, which was once advertised to be published in 2016, didn’t cause this level of ire. Calloway’s explanation, along with her reveal that she was now $100,000 in debt, instead elicited sympathy.

As she explained to ManRepeller in June of 2018, “It wasn’t long before I realized the boy-obsessed version of myself I planned to depict as my memoir’s protagonist was not one I could stand behind. I think there are a lot of people who would have written the book anyways and taken the money, but I couldn’t do it. So my choices were: write a book that wasn’t really about me — that was just about boys — and get lots of money, or back out of the contract and owe lots of money. I chose the latter, and I’m working on changing my business model so I have the income I need to repay them.”

But that chapter is still not closed.

“This is something I'm only just now healing from, but very much still in the process of, because I can make enough money to sustain myself in New York, but I have not figured out how to make enough money to start cutting down on that debt so I can buy back the story to my life,” she told Refinery29.

Calloway prides herself on delivering free Instagram content to her community of 830,000 followers, and despite briefly considering it last year, has not accepted any sponsored work. Profitable workshops could have helped chip away at this debt, which is why Philly, Boston, Portland, and Denver, which did not sell out like Calloway’s other dates, were ultimately cut.

“After the first weekend — after the first day — I realized that I needed a team to travel with me to every location, and that I would need to pay this team to help me during the week,” Calloway explained. “[The dates] could not support me and two other people, possibly three, coming to that city with hotels and flights and also paying them for their time at the event. I realize that it's frustrating. It's frustrating for everyone to assume every change that I made in this tour is somehow a response to a Twitter thread because I was learning as I went, hearing and hiring that staff. Those are lessons that I would have learned quietly by myself had the world allowed me that chance.”

When it came to dropping her book deal in 2017, Calloway’s community rallied around her. But this latest controversy was a bridge too far, and the virtual friend group began to fracture. One fan wrote an open letter to Calloway criticizing how she handled the tour, while a couple of fan accounts posted statements distancing themselves from the influencer, and have since rebranded.

“I am so grateful for my fan accounts. I appreciate their time so much, and I wish them all the best because I think they’re such funny, kind, creative individuals,” Calloway said when asked about certain accounts’ decisions to part from her. “I had this really hands-on, intimate, engaged approach to them, but it set up this really bizarre dynamic that I did not anticipate.I did not know how to deal with once it had been established. They really felt entitled to special access to me. To be totally fair to them, maybe they are. If you make a fan account about someone, maybe you do have the right to expect them to respond to your messages or to answer questions when you ask them..”

Calloway’s brand thrived because of her eagerness to form personal relationships with any fan who wanted one, tagging them in her stories and commenting on their posts, answering their questions with no topic off-limits. That, she says, is what set her apart from traditional celebrities, or even prominent YouTubers. Nevertheless, even us normal folk don’t owe anyone unfettered access to our personhood, and now Calloway must figure out how to maintain her friendly reputation while setting boundaries.

One way is to bring back the tour. Shortly after cancelling, Calloway announced the workshops were back on. She was going to look her doubters in the face and keep marching on, but she wasn’t the only one receiving abuse. While the public may have turned on her, her fans fired back. Donaldson, who wrote the viral thread and later an article about the saga on Pajiba, is currently off Twitter, citing her mental health.

“For reasons that may be obvious to many, my mental health is not in a good place right now so I will be off Twitter for the next few days, maybe weeks depending on how I feel,” she wrote. (Donaldson did not respond to requests for comment.)

It did not help that for a brief moment, Calloway was selling T-shirts with the slogan “Stop Hate-Following Me, Kayleigh.” However, Threadless removed the shirts after they were made aware that they violated their harassment policy.*

“I want to be respectful of her mental health,” Calloway said. “Although it does help me to laugh about [the controversy]. I do think after all the many, many, many jokes she has made about me, I think if the world were truly fair, I would be allowed to make one joke about her, but the world is not fair.”

Instead, she will be releasing merch that simply reads, "SCAMMER."

Upon reflection, Calloway says her “empathy for Kayleigh has only grown with every passing hour of this situation, because I've really seen how many abusive, mocking things people make in the world.”

What began as a workshop, and commentary on a workshop, turned into something ugly, and something beyond either woman’s control.

“Fifty percent of these people are like city dwelling people that look normal, and if I met them at a party and looked at their Instagram, I would not be like you’re spending your free time sending public figures paragraphs of abuse,” Calloway said. “That's what blows my mind.”

It’s likely neither of the women thought their words would leave the communities they were designated for, and neither explicitly encouraged abuse (after her thread went viral, Donaldson demanded readers not “leave shitty comments on her social media, for fucks sake”), so who’s to blame?

“I think part of the responsibility lies with the people who make the news,” Calloway said when asked. “Because as a journalist, it's not malpractice, at this point in time, to cite a person's opinion on Twitter and not looked at any other context for that opinion...If you're only looking to Twitter for your facts, you're already looking at a self-selecting, gossipy, opinionated, gleefully snarky group of people.” Calloway herself has 26,000 followers on Twitter, which she mostly uses to retweet other accounts and give the occasional serious update, but Instagram Stories is her primary medium.

While Calloway plans on holding one more New York-based workshop, the full tour is not happening. At least, not now. She’s found another purpose.

“I would love to take on a project that helps combat online shaming,” she said.
“Like what I've been through — and we gotta do something about the patriarchy. I’m not kidding. If a young male entrepreneur sold out a speaking tour across the country and 95% of the people who went liked it, and 80 people went the first weekend, 30 of them in a blizzard...there is just no way the world would have delighted [in] tearing him down the way the world delighted in tearing me down.”

While Calloway believes sexism was definitely at play in the ferocity of the backlash, she clarified that she still has things to apologize for.

“Women should be held accountable,” she said. “I was held accountable for canceling those four dates. We're personally reaching out to fans to apologize. I'm accountable for an apology to them, and it's not something I need to deliver it in the pages of an interview, but to them personally because I am accountable to them for that.”

Calloway's final New York City workshop (for now) will take place this Saturday. She previously invited Refinery29 to attend — for $165. We politely declined.