20Something: Alissa

“I just think it’s so much better to spend your twenties figuring you out, because you have the rest of your life to figure out someone else.”

On a gloomy December day, eager to find some respite from the despondency of the dead of a Chicago winter, I found myself nestled into a deep leather chair in my favorite window seat of my favorite coffee shop. The steady whir of the espresso machine and the clattering of dishes blurred into a dissonant symphony behind me, warm light flooding the space from above. I was nearing the final chapter of the book I was reading; it was Call It What You Want, and I had discovered it where every cool and trendy and seriously literary twenty-something girl finds her book recs nowadays: two hours deep into a TikTok doom scroll. The book billed itself as a “bittersweet tale of love and self-discoveries that explores the complexities of relationships and the challenges of moving on.” (Read: It’s about a situationship. Neighbors to lovers. Score.)

The comfort of my current position having expired, I paused my reading to reposition myself. I glanced out the window before me as I shifted, only to find the – ah – collaborator (??) of my very own situationship (which, unbeknownst to me, was a mere week away from ending, but beknownst to me was definitely not going well at this point) staring back at me through the glass. My heart pounded out a couple of extra-strength thuds as I set my book down; the parallels between its plot and this exact moment were not the least bit lost on me. I watched him contemplate for a split second before he entered the coffee shop and sat down next to me, sweeping in with him one of those dwindling glimmers of hope so characteristic of the end of a situationship that maybe, just maybe, this behavior means it’s turned an unexpected corner for the better. As it happens, that was not the case. 

“That’s iconic.” 

Alissa DeRogatis smiles at me through a Google Meet window – it’s a little over a year later, and I’ve just opened our interview by regaling her with this story in the rambling manner I’m prone to. I shuffle notebooks and pens around my desk as we bounce introductions back and forth, making sure I have all of my questions at the ready. Amongst the smattering of black moleskins that litter my work area sits Call It What You Want in all its hot pink, bubble-lettered glory. “Alissa Derogatis” is printed as the byline along the bottom of the front cover. The first page of the book reads, “You’ll always be my favorite almost.” It is a manifesto of solidarity for situationship survivors everywhere. 

I usually try to avoid conducting interviews virtually because it’s harder to read the intricacies of people’s body language and mannerisms, so I cannot always get a true sense of their personality. But with Alissa, I can tell almost immediately that we’ll get along. We greet each other with simultaneous compliments to the other's Google Meet backgrounds (mine, a well-lit corner of my living room with a pair of bouclé armchairs facing each other as if in conversation; hers, two brightly-colored abstract paintings that match her aura perfectly in a way I cannot quite put into words, but you’d get it if you met her). I’m pretty sure we have the same manicure (light pink base with tiny hearts for Valentine’s Day). As we wander through pre-interview small talk, I can’t shake the feeling that I’ve met her before, but I think it’s just the sense of parasocial familiarity that comes from following someone on social media for a while. 

A blunt delivery punctuates her every word, weaving sentences together as a sure hand pushes a shuttle through a loom. Maybe it’s a product of her New Jersey upbringing, or maybe it’s just the no-frills confidence that seems innate in her, quiet and stoic and unwavering. Whether or not she feels it, I get the sense that she is inexorably sure of herself. 

Alissa self-published Call It What You Want in 2023 to rather explosive internet success. In fact, before it had even been written, BookTok (the aptly-named community of TikTok users who dedicate their content to, you guessed it, books) hung in anticipation of its publishing date; 30 pages (plus a title) into her writing process, she posted a TikTok teasing her idea for a novel that was loosely inspired by her own tumultuous situationship. The video blew up, and the comments flooded in. TikTok hath no comment section like one filled with women commiserating over shared experiences with shitty men. 

“Welp looks like we all went through the same thing this summer”

“i have spent my whole summer getting over someone i wasn’t dating & reading romance novels. 

can’t wait to read this when you finish it”

“girl pls even just drop the rough draft i need it!”

“literally the story of my life, i can’t wait for this!!!”

Well, now she had to write it.

I wonder aloud: was her decision to write Call It What You Want a spur-of-the-moment one? Was it always meant to be a physical book, or did it begin as something more personal and cathartic? She paints me a picture in response to my question: a few years ago, sitting on a beach in the trenches of processing her breakup (Newton’s 4th law actually states that getting over a situationship is, like, way worse than getting over anything else), she flipped through happily-ever-after after happily-ever-after. Don’t get her wrong, she loves happily-ever-after books. But. 

“I realized that… they weren’t making me feel like I was gonna meet that person. I knew, in my heart of hearts, that I wasn’t just going to get over this guy and then meet someone [new] in a year. I kind of could’ve told you, at least, that I’d still be single now. So I wanted to write a book like that.” Books are missing heartbreak, she says frankly, and Call It What You Want was born out of a desire for more stories like her own – stories about loving big, losing big, and learning a lot about yourself in the process. “I’m trying to almost create my own genre of romance, I think.” 

I ask her if writing a book about an intensely personal experience is something her younger self could have ever imagined. Writing is a vulnerable form of expression in and of itself, and having that compounded by baring one’s own heartbreak to the world must be a scary thing. That is to say, I would be scared to do it. “I think I was attention-deprived from my situationship,” she admits laughingly, then turning more serious. “I thought I was, like, not important and not enough, and having that reassurance that other people felt that way, plus the fact that people wanted to read something that I was gonna write felt really cool and helped heal me.”

“At what point in your life did you start writing?” I ask. “At what point did it become, like, a significant outlet for you?”

She loved to songwrite in high school (“I was one of those Tumblr kids… I just loved the deep quotes.”), and turned to it often as a means of expression. But songwriting felt too intimate for a dorm room with paper-thin walls, so she hung it up for a bit in college, turning instead to more editorial ventures like The Odyssey and Her Campus. She never set out to become an author, though – she kind of just stumbled into it. But to be fair, she didn’t really set out to become anything in particular. She preferred more of a try-things-I’m-interested-in-and-see-where-they-take-me approach to her career. 

What would her younger self think of her literary ventures, then? “I’d like to think if I met my younger self, she would be so impressed,” she says. “The book stuff was never on the table, and [now] being able to speak to rooms of 50, and 100 people is absolutely insane. And now, looking back, I’m like, ‘Oh, I always wanted to do this in some capacity. I used to sing at talent shows. This is what I’m meant to do.’” 

By “this,” she actually means “reach an audience.” She was always meant to reach an audience.

Here, we slip into a sidebar that is really a discussion between two writers, not interviewer and interviewee, wherein we discover that we share a love for connecting with audiences through our writing. As we both toy with locks of dark brown hair, hers flipped in at the ends, mine curling back over my shoulders, I tell her about my own foray into writing, and how it’s taken the place of ballet as an outlet through which I can connect with people. Simply put, it is my second stage. 

“I love writing, and reading my writing, but that’s harder for me than talking about my writing [to promote it],” she tells me. I find this refreshing to hear. It’s a reminder that writing, like any profession, is multifaceted, and some writers enjoy parts of it more than others. A marketer now by trade, she loves the public-facing parts of authorship. In a sense, the act of writing itself is more of a vessel that carries her toward her readers, connecting with them as the final destination.

From the beginning, Alissa never intended on querying the book (non-literary friends, that is, in short, the process of pitching your book to a publisher). She didn’t want to deal with the red tape of traditional publishing, nor did she want to go through a lengthy editing process – what she did want was to get her book out into the world as soon as she could. Call It What You Want was meant to be therapeutic, and not just for her, but for the thousands of girls who found community in her comment sections. And lest we have any skeptics in our midst, let me make one thing clear: Alissa did not write this book to get him back. She did not write it to expose him, or to embarrass him, or to sic internet trolls on him. Instead, her motivation was intrinsic; she wrote it as an outlet for the insecurities that stem from feeling unwanted, and to give herself grace for them. She never meant for it to lead to all this.

“All this” includes, but is not limited to: a deal with a publisher to republish her original novel with more to follow, a book tour, and tens of thousands of adoring fans of her work. All this, indeed.

It began as a snowball effect, really; her goal for the first week of being self-published was to sell 100 copies. She sold 1000. Within another week, Call It What You Want became the #1 New Adult & College Fiction book on Amazon. When an agent reached out to her, she says, it was like, well now I have to keep going. As personal achievements are wont to do, the serendipitous success of what began as a passion project left her hungry for more. And if her goal was to get Call It What You Want into the hands of situationship survivors across the globe, being traditionally published was the thing that could propel her past her early accomplishments and into even more substantial territory. And so it did.

Far from her songwriting days of yore, Alissa now finds herself working on her second and third novels, diversifying her sources of inspiration as she goes. She likes to crowdsource, she says, figuring out what her readers are craving, or the kind of message they might want to hear, and then pulling on her own experiences to drive the story forward. She takes bits and pieces of inspiration from the world around her, puzzling them together into a narrative. Also heavily influential? Music. 

When I ask her whether music holds any influence over her writing process, I know it’s a leading question, one that a single rifle through the pages of Call It What You Want could answer. The page before the prologue bears a QR code and a single line of text: “If this story could be told through songs:” Scan it, and you’ll be led to a playlist that could only have been curated by a girl who yearns, peppered with the likes of Lizzy McAlpine, Gracie Abrams, Olivia Rodrigo, and of course, Taylor Swift. I say “of course” because, in case you’re not well enough versed in the Swiftie-verse to have picked up on it by now, “Call It What You Want” is the name of a Taylor Swift song. A quick spin through its Genius page reveals lyrics such as, “All my flowers grew back as thorns / Windows boarded up after the storm,” and, “And I know I make the same mistakes every time / Bridges burn, I never learn.” Rather on the nose, given the plot of the book. 

I’m correct in my assumption that the musical references were intentional. “Music is… such a cool way to have something happen to you, and write about it and then, you know….” She trails off for a moment, searching for the right words. “I don’t know, just, the meaning of lyrics to me can mean so many different things, and I think that they’re also tied to certain times in your life, or memories.” Too true – all it takes is a mere eight counts of Fetty Wap’s “Trap Queen” to launch me back to a stifling frat house dance floor (though I don’t think this is exactly what she means).

She also finds that certain lyrics have the tendency to conjure up a plot line for her to write. “I do think music and lyrics that move me… inspire me. But the song “Call It What You Want” did not inspire the title [of the book],” she adds. The inspiration actually came from a line in another one of Swift’s songs, “All Too Well (10 Minute Version): “You never called it what it was.” Different song, perhaps, but on the nose it remains. Either way, it seems we have Miss Swift, and in a larger sense, music as a whole, to thank for some of the more poetic arcs of the book. After all, songs are stories with rhythm – proof that music and emotion are intertwined, each inspiring the other.

And on that note, we turn to matters of the heart.

I wonder if Alissa approaches dating any differently now, having had her love life strewn across the pages of a book, and the internet beyond. While Call It What You Want is far from a play-by-play of her own experience (she makes a point to emphasize this several times), it draws heavy inspiration from it, and she’s become somewhat of a beacon of comfort for many a jaded 20-something girl on the internet. While I can only commend her for her decision to share her experience so publicly, I wonder if it’s changed the way that she looks at her prospects, or the way her prospects look at her. 

The most noticeable change she had to make was getting comfortable explaining the impetus behind the inaugural work of her oeuvre. That is to say, it’s conceivable that suitors may wonder if their own actions might one day end up woven into the plot of one of her books. Men are bound to come across her work (stay vigilant, girls; they’re getting better at covert online perusals these days), and the nature of her content mitigates any possibility of flying under the radar. She’s had to learn how to explain how she fell into author-dom, and to accept it gracefully when a man bows out after hearing about it (often not-so-gracefully). 

Beyond that, it’s her standards that have shifted the most. “I was not myself for those five years [of my situationship],” she explains. “I couldn’t have been more unhappy, and more insecure, and more sad, and…” the list goes on. Standing firmly on the other side of it all, she knows now that she will never put herself in a box for another person again. Her confidence has grown, and with it, an indefatigable ability to walk away from someone who isn’t meeting her standards. She knows what she wants, and has no interest in wasting her time on anything that falls short of that. She says of settling, simply: “I don’t want to do that.”  

As an afterthought, she adds, “I don’t even think I could do that. I don’t think I could come home every day and look at someone and be, like, ‘Ugchhh.’”

“No, seriously.” I shake my head in agreement. 

I decide to take this as my opportunity to try and share a moment of relatability (if the whole girl-in-her-twenties-who-loves-to-read-and-write schtick hasn’t done it already): I humble myself before her by declaring that I am the queen of ill-fated dalliances (read: I never make it past the talking stage), and she accepts me with metaphorical open arms and a literal nod of sympathy. If you’ve had the misfortune of being swept up in one, you know that it only takes one bad situationship to send your walls shooting skyward, as high as they’ll go. Situationships are not for the faint of heart, and neither is the decision to walk away from one. 

In the realm of could-have-beens and almosts, women can rarely win. We’re scorned for not leaving sooner, scoffed at for being too forgiving, yawned at when we take too long to get over it, and further yet ridiculed for the ways we choose to do so. In short, the onus is usually placed on us. “Everyone loves to blame women,” she laughs humorously when I point this out. 

“Always,” I mutter under my breath.

She goes on: “It takes a really strong person to walk away from something. Especially women,” she adds, “because we’re lovers, we want to believe the best in people and really see them through.” Here’s my two cents: these types of situations are far more a testament to womens’ ability to be caring, and nurturing, and forgiving, and all the things a good partner should be, than to their lack of resolve. The world has set out to paint these traits as feeble, or spineless, but I think we all know (and I speak to the girls and the girls alone here) what a gift they truly are. It is far better to have cared deeply than to never have cared at all.

Our conversation begins to wander as we commiserate on the experience of being single women in our mid-to-late twenties. In my little Google Meet square, I catch myself nodding vigorously in agreement with everything she says. Every time I meet another girl around my age who carries the torch of lifelong singledom, a little part of me relaxes. It’s as if I’ve found kin. 

If these were Austen times, we’d be well on our way to spinsterhood by now. And yet, barring the probing questions at every family gathering (seriously, please stop) and the conciliatory pats on the back from friends who wear their relationship status like a badge of honor (congrats, you have a boyfriend, do you want a medal or something??), it’s liberating to know that at an age most previous generations would’ve been married by, you can stand quite firmly on your own two feet. You can provide for yourself, and support yourself, and entertain yourself, and when you tire of your own thoughts, you can turn to your friends. If you’re as lucky as I’ve been, you’ll find your time filled not with a relationship you’ve settled for, but with the ringing of your friends’ laughter and many a rapt memory to be held dear.

And then, of course, there are the brief but inevitable moments when you realize that you are the only member of your college friend group who is not engaged or married, and you’re back to wondering if perhaps you should give manifestation a try.

When I mention this, Alissa counters with a question: “What’s the difference in getting married at 25 versus 32?” All she plans on doing between now and her early 30s is setting herself up for success. She paints a rather unpleasant picture of what life could look like when it’s built as a lean-to on someone else’s foundation. She doesn’t mean to sound grim, she assures me, but what if you build your whole life around someone who might not be there one day? “I want to make sure I’m so, so, so, solid on my own that I’m bringing someone in because I want them, not because I need them.” She wants to be able to set herself up for a happy, successful life, whether or not it includes a man. She’s done it! She’s hit the nail on the head!

There is no cynicism in her words. Instead, they’re sharpened with a determination that I know well, honed by a resolution to stand alone for as long as she needs to. “I do think love is this great, amazing thing, and I want it so badly. But to put everything on the line, just for a relationship is crazy.” She refuses to become someone whose relationship becomes their entire personality. “I just think it’s so much better to spend your twenties figuring you out, because you have the rest of your life to figure out someone else.” I’ll take “Louder For The People In the Back” for 500.

I’m nodding along so enthusiastically I think I might give myself whiplash. “I think the pros of being single in your twenties, and for the majority of your twenties, vastly outweigh the cons,” I offer.

Yeah, she agrees, they do. 

* * * *

I ask her what the best year of her twenties has been so far, given, you know, that she’s no longer being weighed down by a man who would probably benefit from a healthy dose of therapy and/or bell hooks (if any men are still reading this and find that they relate more to the antagonist in this story, kindly direct yourselves to bell hooks’ acclaimed novel, “All About Love”). It was last year – 27. She released her book, and then re-released it, and then embarked on a book tour. “I don’t even know if I cried at all that year,” she jokes. “It was just a really, really great year.” I, freshly 27, breathe a sigh of relief. So there’s hope for me yet!

And as we look to the future, what does she hope is in store? She takes a deep breath. “Okay. So I would die for Call It What You Want… to get a film deal.” Aside from the thrill that would come from seeing her characters brought to life on a screen, she explains that this would allow her the financial freedom to be able to write purely for fun, rather than having to put pressure on herself to write something that will sell. She wants to keep expanding her outlets for writing, like on Substack, where she’s working on letting her personality shine through without automatically thinking, “that’s dumb” about everything that spills out onto the paper. (As a Substack girl myself, one who is prone to run-on sentences and unnecessary parenthetical asides, I can relate.)

“And I want to write books for the rest of my life.”

You can find Alissa on Instagram at @alissaderogatis, or on TikTok at @alissaderogatis. You can find “Call It What You Want,” and I highly recommend that you give it a read, here.