Why Is Everyone So Obsessed With Caroline Calloway?

I have a confession to make: I’m obsessed with Caroline Calloway—or at least fascinated by her. 

I learned about Caroline pretty late in the game. There were multiple posts on my Instagram feed about a new article in The Cut about Calloway written by her ex-best friend, Natalie Beach. My first impression of Calloway was that she was a narcissistic and fame-obsessed best-friend dumper. So I scoured her Instagram to see her side of this story, to check if she really was what Natalie made her out to be. 

But after the article died down, Calloway didn’t. In fact, she’s never really died down. She’s been “canceled” more times than you can count, but she still has faithful followers. She has devoted fans who love watching the chaos of her life; she has people who claim to hate her but somehow find themselves refreshing her feed multiple times a day. Why?

Calloway recently released an essay offering her side of the Natalie Beach drama. She charged $10 to read it and ultimately raised $50,000, which she later donated to COVID-19 charities. Calloway had promised her readers that the first part of the essay would be 15,000 words, but it came out to 6,000 instead. She apologized, “My bad! Please accept this uncensored nude along with my humble apology.” Her nude is still her pinned tweet. 

Calloway then launched an OnlyFans account. She’s faced a lot of heat for this tweet, in which she said she’d be cosplaying as a bunch of different fictional characters. The issue? Half the characters are underage children. One user said, “You’re rly fuckin gross for this. Delete everything and reflect.” Another OnlyFans creator responded, “If you’d like to see beautiful lingerie on a lady who doesn’t support sexualizing children, welcome!”

Calloway says she was born into “material wealth and emotional poverty.” Her father went to the prestigious Phillips Exeter Academy and Harvard University; her aunt attended the same schools along with Columbia Business School; her uncle attended Phillips Andover Academy and then Yale. Her family is intelligent enough to get into these schools, and wealthy enough to attend. But along with smarts, her genes contain mental illnesses such as bipolar disorder and schizophrenia. An email she sent to Natalie reads, “I just want you to understand because I don’t think many people do understand the level of trolling that I live with or what it is like to be constantly reminded of your mistakes by strangers who hate you.” People on the internet are ruthless, and I’m sure it’s a million times harder to bounce back from everyone hating you when you deal with mental illness as well.

Calloway gets canceled daily. Recently, she was a guest on Ziwe Fumoduh’s weekly Instagram Live show in which Fumoduh tries to “have a good discussion about race and entertain people.” After Caroline mentioned she’d bought books from Black-owned bookstores, she said, “I would like my ally cookie now.” Ziwe immediately responded, “There are no cookies in this game.” 

Really, what’s interesting about Calloway’s appearance on the show is that she called herself out. She said, “I think it’s really weird that white women come on this show and they’re like, ‘I’m not racist’ when I really think white women should be coming on the show and being like, ‘I’m so racist’ because I think everyone is very racist, and I think that people who deny that they have that poison in their brain are lying to others and especially to themselves.” Ziwe seemed to agree with this. Calloway’s Instagram comments, though, are full of disapproval. One user said “Very disturbing interview….”; another remarked “Wow, you fucking suck.” A comment with 89 likes reads, “Super disturbed by how tone-deaf the footage from the Instagram Live you did with @ziwef was. You shouldn’t get a ‘cookie’ for being an ally. Literally pick up a book, read it, and don’t act like you’re so progressive just because you’ve read a few books by Black authors.” Ziwe herself tweeted, “Watch the interview that Caroline Calloway describes as having gone ‘well.’” 

If Calloway is so problematic, how on Earth is she still relevant? Because she’s real. She may not be honest 100% of the time, but when is anyone? She’s had to explain her own friendship to thousands of people. She’s a talented writer, even if she didn’t write all of her Instagram captions herself. Natalie said in an interview with The New York Times, “Her voice is really singular, and I think that’s the reason why she’s a figure who has over the years persisted in our culture.” So while I don’t agree with most of what Calloway says, I still empathize. Her life is broadcasted to hundreds of thousands of people, she’s constantly depicted in well-known news outlets as a joke, and her father committed suicide two days after her ex-best friend broadcasted her past mistakes from a time when she was addicted to Adderall. 

Though Caroline has countless haters, she has fans, too. When she posted videos of herself crying on her Instagram story, a fan responded, “I’ve followed you since 2013; you’ve made mistakes and you’ve made art and your experiences are valid. As a woman also just trying to do her best, I’m appreciative of all of the different kinds of content you’ve made over the years-from myself and all the other messy girls—THANK YOU.” When Caroline shared her discontent with a Daily Mail article, there were supportive comments, like “You helped so many by sharing your experience with depression. You put into words what is difficult to express and to communicate. You were brave to do it. These parasites are just trying to make money off of you.” and “I love you Caroline!”  

Caroline was born an influencer. She always knew she was going to be famous—she changed her last name at seventeen because she thought her middle name would look better on book covers. On being canceled, Caroline says, ”[it’s] much like getting caught in a riptide. If you fight against it, you will expend all your energy, and you will drown… I think it’s so unfair that people look at the ways that I let myself be carried by the current—the only other choice being to let it break me.” 

It’s impressive how Caroline has survived being canceled. Most influencers that are canceled are forgotten about, but Caroline always seems to stay afloat. It’s puzzling how someone who hates being caught in the “riptide” always finds herself in it. She has to be canceled, or else she isn’t famous. She loves fame so much that she’s willing to risk her reputation for it, because she’s willing to risk bad press over no press. Most couldn’t take their name being dragged through the mud once, let alone multiple times. Caroline is fascinating because of her ability to stay on everyone’s mind, to stay relevant no matter the cost. She’s not giving up even after millions of people read her ex-best friend talk about how awful she was, and I think that deserves a little bit of applause.

By Chloe Rose