Confessions Of An Overnight Broke Person

When I ordered Seamless last night, I theoretically knew there were only two exit paths — either I would talk myself into cooking the perishing groceries in my fridge and exit out of the online ordering app, or $40 would exit from my wallet. I didn’t really think about it when I started adding various specialty sushi rolls to my cart. I thought that it would cost a little bit, maybe $20. You don’t think much about $20; it’s not life-changing. After seeing how much I was throwing into my cart with reckless abandon, my roommate said, “You know that’s going to cost you like, $70 right?” I thought she was delusional. Then, I hit “proceed to checkout.” That’s how I learned my dinner order was going to run me $83.67 before tip.

It’s not purely a celebratory time. Sure, I’ve temporarily alleviated the responsibility of having to cook my own meal like a functioning adult, but it’s a stressful time, too, because of the constant decisions. Is 16 rolls enough, or will I still be hungry after? I’m always hungry like, an hour after I eat sushi. Should I get an appetizer of edamame? Do I sub out a dragon for a California roll, or is that embarrassingly basic?

Of course, once I saw the total, I had a brief moment where I asked myself, should I even be doing this? That’s like, 6 months of Netflix — or maybe 5 since they keep upping the price. I don’t know. But then I considered the alternatives: opening that can of black beans that I bought “in case of emergency”, which would require wiping off the film of dust that’s collected on top of it; figuring out what to do with said black beans; maybe boiling water for some pasta? And then pretending like eating plain pasta and canned beans with a spoon is a normal and not at all sad meal. I should really invest in a rice cooker.

There are things that rich people do, and from what I’ve learned from watching Arrested Development from my roommate’s ex’s Netflix account, pretending like your problems will go away if you ignore them is one of them. So I hit “place order” on my small army-sized portion of sushi, not thinking about how it would bring my checking account balance to $2.94 and especially not thinking about the birthday drinks I promised my friend I’d go to on Friday. I resolved to sell some of the clothes I don’t wear that much on Poshmark to make up the difference—“gently used” is subjective, right?

At this point in my life, nothing is going to change. What would I do differently, aside from budget, exercise self-control, or say no to social obligations? I’m only having as much fun as my peers are. So if they’re going to brunch, why shouldn’t I go to brunch? Never mind the student loan debt I’ve barely made a dent in despite making the minimum payments for eight years. (Talk about not thinking much about $200,000.) I keep a shrine in my closet to President Biden and pray every day for him to forgive student loan debt, so I’m doing my part.

What would I really do with the money aside from pay my bills or donate to my 401(k) that, similarly to my emergency black beans, is also collecting dust? It’s not like I’m ever going to be able to afford to buy a house. And even if I could, Williamsburg feels like it has peaked and is going downward. I walk my dog at 1pm, and I pass like, two different açaí bowl places that have closed down. I think that’s unsustainable. Shit, that reminds me—I forgot to pay the premium on my dog’s health insurance this month. Hope he doesn’t need any serious dental surgeries.

Guess I’ll have to open up a dating app and line up a few dinners for next week. Most of my friends are getting married or having kids, and I guess I should technically be looking for someone I could bring as a plus-one to their weddings, but my more immediate concern is finding a plus-one for happy hour on Thursday.

What’s that saying, you can’t take it with you? At the end of the day, even if I did get to a point where I was somehow making a lot of money (like maybe I won the lottery?), I could just lose it all. Isn’t that what happened with Yahoo? It was the darling company in the 90s and know I don’t know if it exists. I think about Yahoo constantly, but not enough to have ever typed it into the address bar of my laptop, phone, or tablet to see if it’s still around. I guess I could look that up. Hey Google…

Images: JP Valery / Unsplash

We’ve All Had A Friend Like Caroline Calloway

If you haven’t already read Natalie Beach’s tea-filled essay about her friendship with influencer/scammer (scamfluencer?) Caroline Calloway, you may have at least heard about some of the more sensational points. The life of an Adderall-addicted manic-pixie-dreamgirl-esque influencer, wreaking havoc in a foreign country and drunk off her own (bought) Instagram power, is pretty much the stuff social media dreams are made of. I’ve followed Calloway for a while, after several articles about her various scams—including the time she ordered 1,200 mason jars to her own home for a “speaking tour” that got mostly canceled—alerted me to her beautiful yet terrifying Instagram presence.

I started building up anticipation for Natalie’s article last week, when Caroline told the world the it was coming via her favorite medium: the novel-length Instagram caption. Caroline ultimately posted about the story eight times before it came out, and since it has come out and my writing this article, she has posted about it 42 times. Yes, forty-two. My guess is by the time you read this she’ll have posted so many times, Instagram is permanently disabled. Following her is about following the improbable life of a probably crazy person, who lays it all bare for the world to see, and also like, might have a pyramid scheme on the side.


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The summer of 2014 is when everything started coming together. I had finally found my voice as a writer. I no longer depended on Natalie to sign off before I posted something. I was writing stories that were important to me and I was getting feedback everyday about how important my stories were to the girls that read them. I had bought a couple tens of thousands of followers, which I had leveraged into a community of thousands of real followers. And it was growing. The reason was this: In the same way that I anticipated the trend towards long captions and using Instagram to tell the stories of our lives in real time, I also spotted the potential for Instagram ads from a mile away. It seems obvious now, but it was a breakthrough then and fucking brilliant when I realized I could pay these large accounts to post about me and target my ads to the kind of followers that I wanted! Because that was the thing. I didn’t want FOLLOWERS. I wanted READERS. So I bought ads with BOOK fandom accounts like Harry Potter, The Hunger Games; The Fault in Our Stars was big that summer. Paying for posts seemed like an outrageous idea at the time and the anonymous people who ran these accounts and whom I paid $10 an af thought I was throwing away my money. I gain 150,000 followers over the following summer. I didn’t know it then, but this summer in Sweden would be my most emotionally stable and creatively productive for the next five years. Only THIS SUMMER have I exceeded the levels of artistic output that I achieved that summer. Secluded in Sweden with Oscar that summer where midnight never comes and the end of summer vacation doesn’t come until October (!) I wrote and wrote and wrote.

A post shared by Caroline Calloway (@carolinecalloway) on

Despite Caroline’s desperate desire to post “relatable” content, her life has always been hilariously far from anything I, or any typical human, would experience. For example, I have never accidentally ordered 1,200 mason jars to my home (though I am getting married next year, so who knows?). But in hearing Natalie’s story, I realized there was a role for me in Caroline’s crazy world, and it was the role of the traumatized friend. The girl caught up in her friend’s fake “adventure girl” persona, who falls for her magnetic energy, only to get burned in the end. Underneath the story of Caroline ripping up the floors of her pill-strewn Cambridge apartment and the mysterious disappearance of some Yale plates (#WhereAreThePlates), is a story about a toxic friendship coming to its logical conclusion. Ultimately, it’s a very common story, with a pretty filter over top.

The relationship Natalie describes between herself and Calloway is one that was familiar not only to me, but to many of my friends. The toxic cocktail of jealousy, love, anger, fear, and desperation that Calloway inspired in Natalie was something we’d all felt at some point, towards someone we considered a friend. Were those toxic friends famous influencers who lost us thousands of dollars by failing to complete the terms of their book deal? No. But were those relationships similarly painful, traumatic, and difficult to end? Absolutely, yes. A lot has been made of toxic romantic relationships—how to spot them, how to get out of them, how to deal with them once they’re done—but the toxic friendship is the toxic relationship’s annoying younger cousin, and it can be just as hurtful and hard to process.

The end of my own toxic friendship took almost a year from when I realized the damage the relationship was doing in my life to when I finally decided to cut contact. One of my biggest epiphanies that led to my ending the relationship once and for all was when I realized I was behaving like someone who was being abused. I lied to my friend about where I was going because she’d get mad if I hung out with other people. I dreaded seeing her, but also desperately wanted her to be happy with me. I found myself daydreaming about something—anything—that would end the friendship, not realizing that I had the power to end it myself.

I wrote about an intoxicating, formative, challenging, infuriating, and deeply important relationship of mine for The Cut

— Nat Beach (@Nat_Beach) September 10, 2019

Like Natalie, my toxic friend brought out the worst in me. She made me feel small. She sucked me into her drama and made me responsible for her successes and failures. I was a worse friend to others because she was a bad friend to me. I hated her, but I also followed doggedly in her footsteps, begging to be included in the crazy adventure that was her life.

That’s not to absolve myself of any wrongdoing. Also like Natalie, I was as much a part of the relationship as my toxic friend. I encouraged some of her worst decision-making, watching on the sidelines as she blew up her own life time and time again, all because I thought it would make for a crazy story. I was the Gretchen to her Regina, and the most shameful parts of the whole relationship were the times when I watched her inflict her toxicity on other people and cheered it on. Because if she was losing her sh*t on someone else, she wasn’t losing her sh*t on me, right? When she broke into a boyfriend’s bedroom (multiple times) after they broke up, I laughed it off as her being crazy. When she broke into my bedroom after getting angry at me over text, I realized how frightening that type of “crazy” could be.

Who among us hasn’t met a magnetic person that they just couldn’t help but want to be around? One who gets close too quick, and the next thing you know you’re years deep in a friendship with someone who, based on your knowledge of true crime, might be a f*cking psychopath?

The story of Caroline Calloway is the story of an unhinged influencer who will stop at nothing to seem “relatable” to her followers. What’s funny to me is that the first thing that ever made her actually relatable was the one thing she tried to hide: a toxic relationship with a friend.

Images: carolinecalloway / Instagram; Nat_Beach / Twitter