Caroline Calloway: my hurricane diary

I promise I’ll get to the hurricane stuff, but first I just want to take a moment to appreciate how rare it is that I’m even writing this — and how special it is that we can gather together like this inside my sentences, in The Spectator, a place that is famously way more boring and more well-respected than my social media or my books. (Although the Washington Post DID call Scammer “a masterpiece” and the New Yorker DID say “Scammer is funny, engaging, and full of genuine insight,” which is what I would like my tombstone to say when it finally is my time to go!)

There’s a lot of writing in print and online about me and comparatively none at all by me. This is by choice. I’m not complaining! It took me ten years of fucking around in downtown New York and British Cambridge, and then uprooting my whole life to retire from the plot in sunny Florida, to produce just one book. It’s not like I’ve had the prose to spare!

That is, until recently. My second ever book is about to come out — my second in two years! This new “baby sister but not a sequel” to Scammer is titled, iconically, Elizabeth Wurtzel and Caroline Calloway’s Guide to Life and, in order to celebrate me finally starting to feel like I’ve found my footing writing-wise, I’ve accepted my second ever piece of freelance journalism! I only hope it goes better than my first. That piece haunts me to this day because the editors there absolutely DEMOLISHED the punchy, plucky, personality-heavy bit of experimental memoir I submitted to them, rearranging my sentences and clipping them down into flat, humorless nubbins until all that was left was an essay by an alien trying to fit in among human Swifties and my everlasting shame. Let’s hope the editors at The Spectator are less risk-averse and more chill about odd jokes. If you’re reading this sentence because they haven’t cut it, we’re already off to a fantastic start!

So how about that hurricane that everyone told me would kill me? Let’s start on Tuesday.

Shall we?  

We shall.

7 a.m.

I wake up to the headline that I’m going to die today. Not just news stories saying that Milton will be a Category 5 hurricane. But headlines saying I, specifically — my first name, my last name — am about to die. I snooze my alarm and go back to sleep. This feels like a problem for 11 a.m. Me.  

To be more specific: a lot of these headlines are quoting me, saying I said “I’m going to die,” which I totally did. But I said it as part of a larger sentence within a larger paragraph in the opening of a video for Instagram. On Instagram, as on the page — as in online freelance journalism assignments — it’s very important to hook your audience’s attention within the first few seconds. Sharp-eyed readers will note I included the exact same phrase (“I’m going to die”) in the lede for this very hurricane diary! But when it comes to social media scripts versus “real writing,” the rules aren’t fair.

No one but an idiot would take an excerpt from a fellow writer’s lede and report on it without reading the rest of the original thesis first. On social media, however, you can open your video with a catchy, attention-grabbing hook and it matters not at all to journalists how you walk your point back from the opener or qualify with detail. Every word you say is eligible to be quoted out of context and with disdain — quoted in the same snarky tone with which white journalists cited rap lyrics in the mid-1990s or all journalists talked about reality TV stars in the mid-2010s.

I’ve been waking up at 5 a.m. all week and yesterday I ran ten miles in preparation of a Rest Day today. I decide to sleep in.

11:30ish 

I finally get up and check my phone. Everyone I have ever met in my entire life has texted me during the night. Friends! Lovers! Celebrities? Celebrities!

I know I am never beating the attention-whore allegations if I admit this, but here’s the truth: I love this. I already acknowledged to New York magazine that Ziwe texted me a link to a local shelter (which is strange since I thought she wanted me dead!) and I think it was Vanity Fair I told about Emma Roberts checking in? But I will give The Spectator one low-stakes, exclusive bit of Hollywood-influencer crossover-gossip and then shut the fuck up so as to not prematurely fumble any budding celebrity friendships for myself. Lily Allen DM’ed me on Instagram saying she was thinking about me. That’s all you get! Behind the scenes, I already have my own history with these three people and so I feel very certain that name-dropping them publicly is not going to irrevocably fuck up any of the good things we have going. But damn: should I refuse to evacuate from hurricanes more often!? (There’s your pull-quote, folks!) Famous people I’ve always admired and dreamed about befriending someday are finally stacking up in my inbox. How did all these famous people get my number? I still don’t know.

Here’s my theory: maybe there’s some kind of industry database? Maybe?! I think this only because in addition to all the celebrity texts there are a shit ton of texts from reporters I’ve never met.

Who is giving my number out and will they please stop giving it out to anyone who is not a mentally ill famous woman?!

I leave everyone on read. Best friends, lovers, reporters, celebrities. I have work to do. The reason I stayed behind is to help my elderly neighbors because I’m a fame-loving saint who contains multitudes.  

11:35 a.m. 

Actually I do send one text because I’m also petty as hell. I text back this rich, short, dentally-deformed boy who wronged me, but was very good in bed. He said: “Hey I heard about the hurricane. Is there anything I can do to help?” I copy and paste the link to my Cash App and say, “Yeah! There actually is something you can do! Send me money and then delete my number! Thanks!” 

Just kidding. I don’t engage with him at all because saying anything would just be starting something back up again and — although I’m a mess in many areas of my life — taking lovers and keeping them in line is one area I have on fucking lock. (Buy my new advice book!) This is just a rage fantasy I think about as I ride the elevator up and down, making the rounds to check in on the old ladies who were my grandma’s best friends when she was still alive — and now are my best friends here in Florida. I’ve inherited these wilting-flower dames like heirlooms. 

12:30-4 p.m. 

That was quick! As it should be. The hurricane is arriving tonight and it’s not like the grocery stores are still open or that there is any more window-insulation prep left to do. We did all that on Monday and Sunday when our building had its first of many hurricane meetings and the list of the roughly thirty residents staying behind was finalized. At this point, it’s just social pleasantries and knock-knock-knocking and smiling and chirping the phrase “Just checking in!” over and over again. I love my golden girls. Ruth is a hoot and Terry’s a card and Holly is my favorite, which I feel OK admitting because I know for a fact she is the only one who can use the internet. Hi, Holly! I love you. 

Now that my top priority is taken care of, I can start working through my texts from reporters. From 12:30 to 4 it’s back-to-back interviews and calls. Here’s my thought process as to why I even made time to talk to these journalists in the first place: I don’t want there to be any confusion about the reasons why I stayed.

And those reasons are three: my neighbors need me; I had a terrible experience evacuating from Ian; and my building is freakishly safe. It has three-foot thick concrete walls, a history of NEVER flooding not even once (and it didn’t this time!), hurricane grade windows that can withstand up to 145mph winds and is on the same electrical grid as the hospital.

I don’t think people who are not Floridians understand what it’s like for those of us making decisions about evacuation here on the ground. Traffic is gridlocked up and down the peninsula well in to Georgia and South Carolina. Hotels are surge-pricing and not always the most soundly (or vertically) built. And tornados are a real threat once you go inland — if you have a safe place in which to wait out the storm, the reality is that you’re much better off hunkering down where you are than taking the gamble of being caught off guard by the hurricane in a cheaply built motel or worse: your car. And all that is BEFORE you factor in the moral and ethical obligations some people feel about leaving if they have a close-knit immediate community. Like I do. 

I know a lot of outlets want to use my name for rage-bait like, “Ha ha! Caroline Calloway decided to ignore evacuation orders so she can make content!” I would click on that story, too, just to feel something while I doom-scroll if it weren’t a photo of my own stupid face as the cover image. I get it! I really do. But the truth is a lot more human and humane and nuanced. I stayed for what I believe are informed and noble reasons. Now that I’m here? I might as well promote my new book. I’m shut inside. It’s already started to rain. I won’t be allowed to go outside again for at least a couple days. And God knows reporters are going to write whatever they want about me whether or I speak to them or not. So, I might as well have my own perspective included and make some money while I’m at it.

Let me tell you about the most taxing, least relatable part of my whole day — and this is including when the hurricane finally hit later that night. It’s when I changed into one outfit and then another and then another just to have my mom take the same photo of me at slightly different angles on my balcony. Here’s a truth about media and PR that no one else will be brave enough to tell you outright like I am now: editors and reporters will be nicer to you if you give them a free, exclusive photo. All news platforms are struggling financially. They don’t want to pay to license images (let alone to hire their own photographer!) and the overall spin of the piece will turn out more positive if you just go above and beyond to cooperate.

It feels icky, however. Hurricane photo! Outfit change. Hurricane photo! Is this outfit relaxed enough for weathering a hurricane at home? Outfit change again! Hurricane pho— MOM YOUR FINGER IS COVERING THE LENS WHY CAN’T YOU DO ANYTHING RIGHT. 

She is my favorite person in the world and just hours ago I was a grown adult feeling grateful that she decided to leave her low-lying, one-story house which flooded during Hurricane Ian in order to evacuate to our condo building. (A lot of local residents with friends in the building have evacuated here — the structure is that well known among long-time citizens of Sarasota for being architecturally sound.) Now suddenly I’m a teenager again feeling hateful and it’s flashing through my mind that if this hurricane doesn’t kill her — I just might. At 4 p.m., we finish all my press stuff and head down to the lobby for the party. Yes, the party.

4 p.m. 

Vicki has made artichoke dip! I love Vicki and her wife Nina. They are the only lesbian couple in the building and in return for letting everyone think the weed smoke wafting up from their apartment below mine is actually me, they give me unlimited glasses of expensive red wine whenever I knock on their door. I put a hand-knit, blueberry bonnet on my Siamese cat, Matisse, and strap him into his Babybjörn and, no, I will not be elaborating about this sentence further. 

4:30 p.m. 

I have to post. I’ve gained about 10,000 followers on Instagram since this morning, so I say my hellos at the party and then lean my head against my mom’s shoulder and disappear into my phone. I can hear the familiar childhood melody of her making small talk humming through her upper arm, smooshed into my ear. Occasionally someone comes over to coo over Matisse and I look up vacantly and smile. But I’m gone. I’m through the portal. I’m at work. At the office for the job that very few people believe is a “real job” but me. I know. I tap apps.

5-6 p.m. 

I leave the office in the palm of my hand and look up. Oh yeah! The party! I start chugging plastic cup after plastic cup of boxed white wine, but then remember: I have agreed to go on the literal fucking news at 8.  

I fear I have made a terrible mistake. 

6:01 p.m. 

Fuck it. I’m so tired. I need to take the edge off after being “on” during back-to-back calls with reporters today. I used to think I was an extrovert because, in my head, it makes perfect sense that if I believe in my own writing and want the maximum number of people possible to read me, then it also follows that I need to resign myself to doing a certain degree of publicity as part of my career. I’ve since learned that, no. An extrovert is not, by definition, someone who thinks influencing is “a real job.” An extrovert is someone who gains energy by being around people and feels recharged.  

My face drops as soon as the elevator doors slide closed in front of it — elevators which are still working at this point. I stare blankly up into the camp, popcorn-stucco ceiling of my condo as I do my final few steps of hurricane prep. I boil water for pasta, fry up dumplings for tomorrow and fill up both bathtubs. My mom tries to chit-chat with me and I snap at her over nothing, because I am always trying to be the daughter she deserves — and failing.

8 p.m. 

Wow. The timing of going on the news could not be worse, and not only because I’m drunk. THE LITERAL EYE OF HURRICANE MILTON BEGINS PASSING OVER ME BASICALLY THE MOMENT I SIGN ON THE ZOOM CALL WITH CHRIS CUOMO.

There’s like twenty minutes of waiting before I actually go on air and all I can think about are questions like: am I about to lose power? Is this a bad use of my phone battery? What does it look like outside? I’ve lived my whole life in the eye of the storm figuratively, but never literally until now. This moment.

No rain, no birds, not even the chirping of crickets. The bugs have all left, too, and suddenly I can see the stars. How much longer until this moment is gone forever? Am I wasting it in a Zoom waiting room? I want to go to my windows! The balcony! And of course: I want to make content. I know that sounds crass, distasteful, repulsive, even, but hear me out. If you had the choice of spending thirty minutes of your life making Chris Cuomo money while you worked for him and his personal brand for free… or spending that same time making money AND your personal dreams come true (selling books) AND lifelong memories as you witness one of the great mysteries of the natural world… what would you choose? 

Basically as soon as Chris gets on air, I tell him I have to go because I do. Actually, I look into my own eyes on the screen and tell it to my own face. I need to get the fuck out of here — and don’t lie to me and say if you went on the literal fucking news you would go about it any differently! Of course I care about what I look like on TV. And for the record? I looked devastatingly good. Fresh-faced and ingenue-esque. And I feel justified in including this fact because damn have I looked like shit on the news at times. A new era now. 

8:30-11 p.m. 

The end of the night passes in a blur. There is so much to do. First: film eye-of the hurricane content. I take the quickest, most basic fifteen-second video I can muster and I do NOT have time for reshoots because (shocking to my haters) my parasocial branding comes second to my real-life relationships. The condo groupchat is blowing the fuck up. We lose power! More texts! It’s a triage system of checking on my old lady friends. Ruth first because she’s the oldest! No wait, the fabulous gay man in the penthouse named Rich has Ruth covered! Terry then? Hold on, that new guy named Todd is already checking on Terry! Suddenly I have an unexpected assignment instead! My job is Fey and Larry! Elevators aren’t working so I’m PANTING going up and down the building on flip-flopped foot. I tweet! I send texts! I call my mom! She’s somehow on the tenth floor now getting coconut cupcakes (?!) from that gay couple that were such good friends with grandma and granddad before they died. It’s chaos! I squeeze in a brief interview to a reporter from the Washington Post while I’m trekking to fetch a flashlight for Fey because this DC journalist is also in Sarasota for the storm and also experiencing the eerie quiet of Hurricane Milton right now. I don’t think for a second that I, Caroline Calloway, will be his top priority for news coverage come tomorrow. But I do know deep down in my publicist-savant bones that if I make five minutes for this phone call right now, then someday, when I need press coverage for a new book of mine, I will have teed this guy up with the lede of a lifetime: I first met Caroline Calloway inside the eye of Hurricane Milton, et cetera…  

You can imagine how it once angered me when my ex-best friend lied and said she wrote all my Cambridge captions without me and was the brains behind my online brand — and then the whole world believed her.

Spoiler alert: I obviously survived the hurricane, but in case something much, much stronger kills me in the future, I need the people to know one thing while I’m making a rare freelance writing appearance. That hanger-on? She and I fell out of touch during the years I was in England and so I wrote my Cambridge captions alone. I’ve always been the only one engineering my own survival, online and IRL.

And despite being dealt a pretty shitty hand in terms of luck — my father killing himself! Being thrown under the bus by some random girl so she could advance her own writing career! This hurricane hitting the building where my favorite elderly friends are trapped! — I’ve not only hung in there through the worst of it and the thick of it and that’s only the half of it, but emerged on top. 

Fast forward and it’s 11:30 p.m. on Thursday. Listen, I’m not going to tell you what The Spectator is paying me for this piece, but I’ve written five pages single-spaced at this point and I’m done. This piece is over now because if I give The Spectator even ONE MORE WORD of my vibrant, juicy, addictive prose then I will begin to feel like THEY are scamming ME. And nobody wants that feud! These editors don’t want that smoke and I don’t want to fight them. I am clearly holding on to enough bitter grudges as it is.  

But how did the aftermath of Milton play out the next day!? Clearly I didn’t die, but you want the riveting details, you say? What does a city look like in the aftermath of the eye of a storm and why WAS my Mom eating coconut cupcakes during the climax of it all instead of helping? Great question! Well, you curious, gorgeous fools! I guess you’ll have to read my third book to find out — or perhaps my third freelance journalism piece. Whichever one comes first. It’s been five years since I last accepted a writing assignment like this one, so you might be better off clicking this link and buying my books in the meantime. Just because I moved to Florida so that I could focus on my work and retire from the plot, it does not appear the plot has retired from me.

And on that note! Goodbye, dear readers. You have been glorious and gracious and extremely good girls. And Spectator editors, I would like my money now.