Sabrina Waldorf is an Upper East Sider and hopeless romantic. After years of looking for her real- life man in finance, she decided to put pen to paper and create her own trust fund baby instead. When she’s not heading out for bagels or taking a stroll around Central Park, she can be found curled up in her apartment with a good book.
I’m
sabrina waldorf
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I’m Looking for a Man in Finance
I was in love. I moaned.
The bagel to cream cheese ratio . . . perfection. The smoked salmon . . . delightful. The addition of capers . . . genius. The flavors exploded across my tongue with every bite. The rumors were true, and I knew my review of this place would get a lot of attention on social media. This cute bistro had popped up in the West Village over the weekend and there were whispers they could be contenders for one of the best bagel spots in Manhattan. With such high praise already, I knew I needed to be one of the first to review it for myself. I snapped a photo of the bagel with my perfectly manicured fingers framing the logo of the bistro. A beautiful stoop of someone’s house added just the right vibe to the shot.
As soon as I hit post my phone started to buzz as the likes and comments flooded in. I’d carefully crafted my food review page on social media over the past few years, which now reached nearly ten thousand followers and counting. Not exactly influencer status, but not nothing either. I watched the notifications pile up and wondered, not for the first time, if one viral post could
tip me from underrated to undeniable food influencer overnight.
My blog started off as a way to stay sane during my intern days at Sophisticate, the magazine I’m so proud to still work at nearly three years later, now as a full-time journalist, but it had become something more—my creative playground. I covered hole-in-the-wall dumpling shops, farmers’ market pop-ups, boozy brunch spots in Williamsburg, and everything in between. I never missed a chance to pair my bite with the perfect backdrop. Maybe in another life it wouldn’t be just a hobby.
The bustle of NYC continued around me as I stared at my phone, bagel still in hand. The West Village was a brunch-stained love letter to chaos. Flower carts spilled tulips onto the sidewalk. I dodged a golden retriever in a raincoat, sidestepped a painter dabbing at a canvas on the sidewalk, and nearly collided with a guy on a Citibike who yelled, “Nice fit!” before vanishing down Bleecker.
Just another day.
I started walking again, weaving past a man in a threepiece suit as he argued with a pair of twenty-somethings that were filming something in the middle of the sidewalk in front of a vintage bookstore. This was my neighborhood. Messy, vibrant, loud, and beautiful.
The rumble of the subway vibrated up through the ground as I hurried down the stairs to catch my train. I swiped up on my lock screen to look through the incoming notifications when a new post on my feed caught my eye. Victoria, the food critic for Sophisticate , was posing on the streets of London with Big Ben in the background.
I am so excited to dive into the food scene of London, well known for its variety of old and new flavors over this upcoming year . . .
I stopped walking mid-stride, barely registering the curse words flying toward me from the person behind who narrowly missed plowing into me. My finger hovered over my screen as my brain took off at light speed. It couldn’t be . . . That meant . . .
With barely any time to spare, I slipped into the subway, my eyes locked on the phone in my hands. Victoria was gone. Not just on vacation. Gone-for-a-year kind of gone. That post was more than her career update—it was a shining light for me. A slow hum of realization started in my chest and spread through me like a tidal wave. If she was moving to London for the year . . . her job—the job I’d dreamed about since freshman orientation at NYU was officially open.
My heart stuttered. The rattling subway car faded into the background. I’d studied Victoria’s reviews like gospel, analyzed her tone, the rhythm of her critiques, the way she made even a side of roasted carrots feel profound. And now . . . could I be the one to fill that role? Could Sophisticate even consider someone like me?
I didn’t go to Le Cordon Bleu. I certainly hadn’t spent my childhood in Michelin-star restaurants that my parents ate at on a regular basis like Victoria. I was a girl from a small town in Ohio who ate cereal for dinner more often than I’d like to admit. I’d moved to Manhattan with a dream of living in a place where dreams came true and where I could dine at the kind of places I used to read about in blogs growing up. I’d also built something from
scratch—my social media account, all ten thousand followers and counting. Reviews that people trusted. A voice. A perspective. Maybe it wasn’t fancy, but it was mine. But was that enough?
The train lurched forward, and I gripped the pole next to me, the phone still in my hand, screen glowing with Victoria’s smile frozen beneath Big Ben.
My world had just shifted—and I wanted it badly enough; this could be the moment everything changed. I glanced up at the looming skyscraper across the street from the subway station as I climbed the stairs back out into the city. The building housed Sophisticate, a women’s magazine known for covering any topics from sex and relationships to health and politics. It had become a part of the very fabric of American culture, devoted to the concerns of women and their lives.
From the moment NYU ’s journalism program accepted me, I dreamed of working for Sophisticate and still felt grateful every day to walk through those glass doors. There was only one piece of the puzzle missing from my dream— writing as Sophisticate ’s food critic.
When I applied to the magazine out of college, I knew it would take some time before I was qualified to apply for a position that wielded such power within New York’s food scene. So I worked myself nearly ragged for two years as an intern, fetching coffees and teaching my boss how to convert a PDF, before I finally landed my column—“Overheard in NYC ”. It was a tiny column at the back of the magazine, barely two-hundred words per week. But it was a step toward my dream job, covering the most exquisite cuisines across the city.
My notes app was full of one-off comments I’d heard from people around me—on the subway, in my favorite coffee shop on a Sunday, or on my morning run through Central Park. I covered anything from the juiciest celebrity sighting to the newest sex position I overheard some girl telling her friend she’d tried with her partner. I was grateful to even have “Writer at Sophisticate ” on my résumé, but my passion was to write about food.
A text message from my best friend, Roxie King, popped up across the top of my screen.
Roxie: What does this evoke for you?
Attached was a photo of a rounded sculpture that looked nothing short of phallic. Roxie worked at a famous art gallery on the Upper East Side where she sold art and sculptures just like this one to people that had more money than they knew what to do with.
Hallie: Confusion? Of the penis-shaped kind?
Roxie: I should have known better than to ask a sex magazine columnist . . .
Hallie: Hey! I write about more than just sex . . . speaking of which.
I sent her the link to Victoria’s post and stepped off to the side to avoid the morning commuter rush on the sidewalk.
Roxie and I were roommates during our freshman year in college and bonded over our mutual love for food—with my dreams of becoming a critic and hers of photographing the most beautiful plates of food in the world. But neither of us had cracked the code of the
restaurant scene yet, relying heavily on our own social media accounts to make a name for ourselves within the industry. Now we were roommates once more, living together in our tiny apartment in the West Village, as we tried to chase our career dreams.
My phone dinged with Roxie’s reply.
Roxie: Are you going to apply?
Hallie: Why? So they can smile and say “how cute”?
Roxie: You know exactly why. You’re just as qualified to apply for the position as the next person. So why the hell wouldn’t you?
The lobby of Sophisticate was always buzzing—sleek blackand-white marble floors, artfully arranged florals, and a rotating collection of cover stories displayed in gold frames near the elevators. Roxie’s words rang in my head as I stepped through the revolving doors. I was immediately greeted by the scent of espresso and expensive perfume, the hum of heels on tile, and the distant ding of the elevator arriving. There was a certain magic in walking into a building that felt like the nerve center of modern womanhood.
I rode the elevator up with a group of writers and staff, all in various stages of caffeine dependence. One of the girls from the fashion team complimented my boots, and I made a mental note to text Roxie a thank-you—she’d convinced me to splurge on them during a sample sale last month.
When I reached our floor, the open-concept office hummed with energy. There were half-eaten croissants on the community kitchen counter, mood boards pinned up
on the walls, and a fashion assistant dragging a rolling rack of outfits behind her like it was her oxygen tank. Someone in editorial shouted about a missed deadline while another person ran past holding three coffee cups like a juggler in the circus. It was a chaotic, caffeinated dream, and I loved every inch of it.
I dropped my tote on my desk and booted my computer, sipped the last of my bodega coffee and snacked on the last few bites of my bagel. My desk was small, tucked between two other junior writers, but it was mine. A framed photo of Roxie and me at graduation sat beside my monitor, next to a stack of colorful notebooks and a candle I wasn’t technically allowed to burn.
“Morning, Hallie,” came a voice from the desk beside mine. It was Janelle, one of the other junior writers, typing furiously with one hand and balancing a blueberry muffin in the other. Her oversized glasses slipped down her nose as she glanced at me. “Tell me you saw Anthea’s heels today. God, I want to be her.”
I laughed, setting my coffee down. “I haven’t yet. But I can imagine. I swear she floats instead of walks.”
Janelle leaned closer, lowering her voice. “Okay but real talk—did you see the job board this morning? Everyone’s buzzing about Victoria’s position opening up.”
I nodded slowly, the glow of my computer screen reflecting in my eyes. “Yeah. I was thinking of applying.”
Janelle froze mid-bite, muffin halfway to her mouth. “No. Way. Hallie! That’s huge! Wait—do we celebrate this with lunch, drinks, or those cupcakes from that bakery in Chelsea?”
“Maybe all three? But only if I work up enough courage to submit it.”
She grinned. “You’ve got this. You’re basically the only one in here who could write a review that makes me want to lick my screen.”
I smiled at her, the nerves in my stomach calming just a little.
I had an article to finish—something I’d overheard this weekend from an heiress discussing an exclusive club in Hell’s Kitchen—but I kept glancing toward the top corner of my screen, where the company’s internal job board icon glowed like a neon sign.
Maybe Roxie and Janelle are right. Maybe I am just as qualified as the next person. What’s the worst that can happen? They say “no”?
Without a second thought, I logged onto the job board and pulled up my updated résumé. I moved to this city for college to chase my dreams. How was I ever going to reach them if I never took chances?
Victoria’s open position was sitting at the top of the list as the newest opening and before I could change my mind, I clicked into it and applied. Taped to my computer screen sat a picture of my family. I traced my fingers across my mother’s soft smile, then my father’s sun-worn face, and finally my younger sister, grinning wide on her wedding day. They hadn’t understood my enthrallment with New York when I first told them of my dream of moving to the city—they all still lived in the small town in Ohio I’d grown up in, just down the street from each other. To them, life was a quiet neighborhood where everyone knew your name, and Friday
nights were reserved for potlucks or high school football games.
But I craved the unfamiliar. The kaleidoscope of languages on the subway. The pulse of yellow cabs and flickering crosswalks. The smell of halal carts and roasted peanuts wafting through every other block. I wanted more than comfort—I wanted color. Energy. Flavor. They might not have understood my new life, but they were still proud. My very first published column in Sophisticate a two-paragraph “Overheard in NYC ” piece about a woman breaking up with her boyfriend over a taco truck order—was framed in my parents’ living room, right next to my sister’s ultrasound picture. That’s how much it mattered.
And now . . . maybe this next step could be even bigger. Still buzzing from the decision, I clicked over to my current column draft. Deadline looming, lunch forgotten, I chewed nervously on a pen cap and reread the opening paragraph. Last week’s piece had gone unexpectedly viral—and by viral, I mean our traffic spiked just over 3,000 more clicks than usual. But in digital publishing? That was basically a cultural moment.
I had been on my way to pick up a coffee last Wednesday morning when I overheard this twenty-something corporate girl talking to her friend outside the coffee shop near my apartment, while they sipped on their matcha lattes.
“I just go to Whiskey Locker; you know, the bar on West 55th Street? Down in the Financial District?” Her friend nodded enthusiastically, dressed head to toe in
Lululemon. They were clearly on their way to a Pilates class or coming from it.
“And I wait for any guy in a vest and a button up to ask me out. Financial analyst, investment banker, you know, I’m not picky.” The girl flipped her perfectly highlighted blonde hair over her shoulder. “Sure, they all have been fuckboys so far, but eventually one of these finance bros has got to stick around long enough to buy me a Birkin . . .”
After the “Overheard” article went live, our Sophisticate notifications had lit up.
@nycchronicles: I heard this exact convo outside Devocio in FiDi. She was serious as hell. But I can’t blame her. Those finance guys are HOT! #OverheardinNYC
@financebrosanonymous: Whiskey Locker is where careers go to thrive, and dignity goes to die LOL
@lululemonwarrior: Was she telling the truth? Asking for a friend.
Even Anthea Sparks herself had reposted it to her story. I’d nearly passed out when I saw that notification come across my phone. That was the moment I felt it. Not just excitement—recognition.
For a few glorious hours, I had floated through the newsroom like I was wearing invisible heels, three inches taller. I wasn’t just the girl scribbling snarky eavesdroppings into my notes app. I was seen. I was heard. And not just by the audience of Sophisticate readers scrolling through columns during their lunch breaks, but by the woman who had built the entire damn empire.
I felt like I had finally cracked the glass ceiling of irrelevance.
People in the office smiled a little longer when they passed my desk. Someone had even scribbled “future Pulitzer winner?” on a Post-it and stuck it to my monitor. I left it there. A little tacky, a little ironic, but still—not entirely impossible now.
It wasn’t just the clicks, though I checked the analytics way too many times. It was the comments, the reblogs, the DM s from friends I hadn’t heard from since college:
This is hilarious, Hal. More please.
You’re basically Carrie Bradshaw now. Remember me when you’re famous.
I went as far as to order an overpriced cappuccino just to sit outside the same coffee shop, wondering if lightning might strike twice. I even brought a notebook, pretending to look busy while hoping someone nearby would say something column- worthy again. No such luck. Which left me with an old note I’d overheard at a workout class that didn’t feel nearly as punchy for my next article.
Before I had time to analyse it further, Anthea Sparks, my boss and editor-in-chief of Sophisticate, walked past my desk. She was wearing Carolina Herrera and sporting Gucci platform sling-backs that were yet to even hit the runway. She was the definition of “boss bitch” in the very best way and had turned Sophisticate from just another women’s magazine into one that shaped every aspect of female culture.
As she passed me, I barely caught the words, “Hallie, do you have a minute?”
“Oh, yes. Right, absolutely.” Anthea was already sweeping into her office as I quickly closed my laptop and hurried after her. My heart was pounding. This was the first time she’d ever specifically called me into her office. It wasn’t like my boss didn’t know who I was, but I assumed I’d always been just another face in the crowd. Maybe this was the moment that would change everything—or the moment I’d screwed up entirely.
Anthea’s office overlooked Manhattan, as if she were a queen surveying her kingdom. The skyline was framed in the background, the sun highlighting the opulence of my surroundings. It was the perfect blend of luxury and industry. She covered her walls with the pages of Sophisticate ’s next edition. Anthea’s bold handwriting covered each page in sticky notes, detailing her thoughts on the tiniest points. A Peloton bike sat propped in the corner of her office and a clothing rack filled with the pieces the magazine was planning on covering in various articles was overflowing near her back wall.
I stood for a moment in the doorway, unsure if I should sit or wait for her to acknowledge me. Her assistant, a woman with impeccable style and a clipboard permanently attached to her side, rushed by carrying a cup of coffee.
“This isn’t hot enough,” Anthea told her as she took a sip, causing all the blood to drain from her assistant’s face. Anthea glanced up, her icy green eyes narrowing as she sent a signal, dismissing her assistant.
Anthea didn’t acknowledge me, her fingers still tapping out an urgent message on her phone, as if she hadn’t just
invited me to her office. I could feel the pressure building, the soft hum of the air conditioning filling the otherwise silent room.
I used the moment to survey Anthea’s office, the perfect décor, the plush velvet couch, the floor-to-ceiling bookshelves with countless binders, the sleek coffee table covered in glossy Sophisticate magazines. A wave of envy washed over me. Was this what success looked like? I wondered if I’d ever make it to a point where I was calling the shots like she did.
I swallowed, trying to suppress the knot in my throat. This was Anthea Sparks. This was the person who made Sophisticate what it was today. And here I was, just another writer hoping to get noticed. That was if I made it out of this conversation with a job. Because who the hell knew why she’d called me in here.
Finally, Anthea put her phone down and looked at me. She didn’t smile, didn’t offer a pleasantry. Instead, she leaned back in her chair, folding her arms across her chest, her expression unreadable.
“I wanted to talk to you about your ‘Overheard in NYC ’ column from last week,” Anthea said, cutting right to the chase. She wasn’t a woman that afforded herself the luxury of wasting time.
For a moment, I froze, unsure of what was coming next. Was she going to tell me I’d gone too far? Had she changed her mind after sharing it and thought the article wasn’t to Sophisticate standards, after all?
I had to brace myself for whatever came next. She was the picture of composure, like she had all the time in the world. “And it obviously resonated with a lot
of people. So, I was thinking . . .” She trailed off for a moment, as if letting the words hang in the air, before continuing. “This whole ‘finance guy’ thing. It has some legs to it. I want you to take it further. Let’s call it ‘Love on Wall Street’, where you write a series of articles trying to find a date with the most eligible bachelors on Wall Street.”
My mouth went dry, and I blinked a few times, trying to process what she’d just said. Was she serious?
“Wait, sorry—dating? Finance guys?” I stammered, completely thrown off.
Anthea’s gaze was sharp as ever, unwavering as she observed me. “Yes, that’s what I just said.”
I couldn’t breathe. My mind short-circuited as I processed the idea. Dating for a column? This was a whole new level of personal exposure. I was supposed to go on dates, to share my life, my privacy, for the sake of a story? I hadn’t signed up for this.
But I couldn’t help but wonder if I was overthinking it. I had been scrambling for something, anything, to make an impact—something more than just my “Overheard in NYC ” fluff. And this idea? This could blow up. It could make me.
“I . . . I don’t know . . .” My voice was small, unsure. My gut tightened at the thought of dating guys I already found distasteful. Wall Street types? They were everything I despised: arrogant, superficial, heartless. And women like me, just a little too smart, a little too ambitious? We were nothing but objects to them.
But then I remembered the application. Being a food critic had always felt out of reach, just a glimmer in the
distance. If I said no to this, I could kiss any chances of getting that position goodbye.
My first instinct was to figure out a way to backtrack out of this conversation and pretend it never happened. Anthea must have seen the look on my face because she narrowed in on the challenge I was presenting her.
“You know, I saw a notification come across my inbox earlier today.” Anthea pushed off her desk and circled to drop into her chair. Not a single piece of silky black hair moved as she leaned back in her office chair. “I didn’t realize that you were interested in our food critic position.”
“Wait—hold on,” I said, frowning, confusion clouding my thoughts. “I thought we were talking about a dating column. What does this have to do with the food critic position?”
Anthea didn’t even flinch. She simply leaned back in her chair, her posture smooth and commanding, the faintest hint of a smile playing on her lips. “You’re right to be confused. I wasn’t planning on explaining it just yet.” Her eyes narrowed, piercing through me. “But I’ll make it clear. If you can pull this off, write a series that resonates and brings in even more traffic than your last piece, I’ll consider you for the food critic role. It’s yours for the taking. But first, you must prove you can write a story that captivates.”
If I had been speechless before, my brain had simply forgotten the function of speech at this point. I blinked at her, trying to wrap my head around her proposition. A dating column for a chance at my dream job?
“You’d let me go from writing about finance bros to
covering Michelin-star restaurants?” I asked incredulously. Even I thought that was a bit of a stretch, despite my own delusions in hoping for the position.
Anthea didn’t seem phased by my surprise. She simply leveled me with her piercing gaze. “You have talent, Hallie Woods. Even if it may be raw and could use some refinement. And Sophisticate didn’t get to where it is without putting talented people in positions to succeed. If you feel you’d succeed the most in our restaurant critic spot, then I might just put you there. But first you must prove it.” Anthea lifted one perfectly plucked eyebrow at me.
The compliment, however backhanded, nearly made me miss the rest of what Anthea had offered. I had always dreamed of working with Anthea and would have done almost anything for a compliment from her, as would anyone else here, but could I do this ?
Was I going to take the offer? Or was I going to walk away?
My mind raced through the possibilities.
Pros: This could be my chance to prove myself, to elevate my career to something bigger than the “Overheard” column. Anthea herself had said she’d consider me for the food critic role if I succeeded.
Cons: I’d be using my own life as content. Could I really put my personal dating life on display for thousands of readers? It felt . . . exploitative. And what if my dates actually turned out to be not half bad? How was I supposed to throw them into the fishbowl too?
I tried to picture it, sitting across from some Wall Street bro in a posh bar, pretending to enjoy his stories about IPO s and mergers while inside I was cringing. I could
already feel the mockery of it. And even worse the judgment from my peers.
Would they think I was selling out?
I glanced back at Anthea, whose green eyes were locked onto me, expectantly waiting for a response. She had probably seen the wheels turning in my head.
“Are you still with me, Hallie?” she asked, her voice colder now, a slight edge creeping in.
I hesitated for just a second longer, my mind running in circles, filled with uncertainty, but I couldn’t deny the thrill that pulsed through me. This was my chance to step up and prove that I belonged here. That I wasn’t just some girl who wrote about nonsense but someone with real potential. Someone who could write about the most delicious food this city had to offer.
“Okay,” I finally said. “I’ll do it. But just so we’re clear—what exactly are you expecting here? Dates with actual Wall Street guys?” I couldn’t help but add the last part with a bit of sarcasm.
Anthea’s lips curled into a satisfied smile. “Exactly. One a week. But the key, Hallie? You need to make it compelling. We’re not looking for a dating column, we’re looking for a story your story, your journey into the world of finance guys. We want details. Make them feel real.”
A mix of excitement and dread surged through me, but I nodded.
“Alright, I’ll write the first one. But—” I hesitated again. “What if they’re all . . . not great? What if it’s a disaster?”
Anthea leaned forward, her smile tightening. “That’s not an option.”
I felt a flutter of unease. Would it be worth it? What was I willing to sacrifice for success? I was about to find out.
“When do you want the first article by?”
Anthea’s eyes glinted as she checked her watch. “Two weeks. Don’t disappoint me.”
As I turned to leave, the weight of her words hit me again. The pressure, the challenge. My stomach was a storm of nerves, but the truth was, I had never felt more alive. This could make or break me. And I was choosing to make it.
Whiskey Locker provided the best Friday happy hour in all of New York City. Everyone from Wall Street would migrate from the southern tip of Manhattan up toward Central Park to loosen their ties, leaving behind the high-rise offices full of people dealing with the cash flow of the wealthiest people around the world.
This bar drew nearly every crowd in New York—models within the fashion industry, Wall Street mongers, celebrities, musicians, influencers—you name it. They lounged around the dimly lit velvet booths that provided privacy for its patrons. But a crowd like that always drew in curious onlookers, those that wanted to breathe the same air as those with the power to influence industries. Men and women leaned against the bar, hoping for someone sitting in those booths to pluck them out of anonymity and deem them worthy of their time and energy.
But despite the various groups mingling together, there was one profession that had always reigned supreme at Whiskey Locker. They were unmistakable—the tailored suits, perfectly pressed vests, and glinting luxury watches set them apart. These were the investment bankers, financial analysts, hedge fund managers, and everything in between—the true backbone of this establishment.
Or what social media now kindly referred to as “finance bros”. The bar had always belonged to them—to us. And I was proud of it.
“Are you going over to Michelle and Elliot’s for dinner tonight?” Sebastian, my best friend and heir to Whittaker Holdings—the biggest fashion conglomerate on the planet—asked me.
“I was planning on it,” I told him as I tapped my ring inscribed with my family’s crest against my whiskey glass. “Are you?”
Sebastian shook his head. “Not tonight. I have a meeting with an upcoming designer. I’m hoping to close a deal with her tonight.”
“Business or pleasure?” I gave Seb a knowing smirk as I took a sip.
Sebastian Whittaker was many things—a fiercely loyal friend, a business shark, and an exceptional flirt. It wasn’t unheard of for him to mix the latter two for his own personal means. He’d been tossing ethics out the window since I met him back at Princeton, a true hedonist at heart. But that didn’t mean he wouldn’t earn the title of CEO of Whittaker Holdings when it was time for him to take over the company from his father.
Of course, there were always whispers—the “nepo baby” allegations followed him wherever he went as people watched him play the charming playboy. They liked to call him a product of privilege, a rich kid who had coasted through life on his father’s name. But anyone who knew him, anyone who had watched him put in the long nights and fight for his place in the cutthroat world of business, knew that Sebastian had earned everything that came to him.
“Business. Strictly business on this one.” Seb smoothed a hand over his dark hair, the tattoos on his hands stretching. “Elliot wasn’t happy to hear I’d be missing out again tonight. He told me he was going to leave me off the invite list if I didn’t make it to the next one.”
“You know how Elliot gets,” I told him. “He doesn’t want to feel like his relationships are purely ornamental. And he’s not wrong. You haven’t made as much of an effort lately to show up to things.”
“I’ve been busy.” A muscle flexed in Seb’s jaw. I knew that he’d had an enormous amount of pressure on him as he prepared to take the helm of his family’s company, but he never shared enough for me to know where his head was at.
“Right.”
Elliot Granger was the last piece that completed our Princeton trio. The three of us had been inseparable in college. We couldn’t be more different. While Sebastian partied almost constantly and I networked to climb the Wall Street ladder before graduation, Elliot secluded himself in his apartment to learn about the cryptocurrency market. By the young age of twenty-two, he’d become one of the most successful cryptocurrency wallet managers in the world, changing the game for hedge fund managers forever. He was on track to be one of the youngest billionaires in the world. Between all of that, I’m still not sure how he snagged Michelle during our time at Princeton. She was effortlessly beautiful, with a sharp mind to match, and always had a way to make everyone around her feel like they were the most important person in the room. Elliott was a goner the second he laid eyes on her.
My phone chimed with another automated email analysing today’s market. Ignoring the sigh from Seb across from me, I reached for it.
“You could use a little less business and a bit more pleasure, I think.”
With a final sip of my whiskey, I declined.
“It’s been over a year since Cassidy, man. You haven’t even spared a glance at another woman.”
“And I don’t plan to anytime soon.”
At one time, I had thought Cassidy Lark was the love of my life. From the first moment I spotted her working behind the counter of my favorite coffee shop, her energy had enraptured me. She’d been so charismatic, so magnetic, so completely different from every girl that I’d grown up with, that I’d fallen head over heels. I had thought I’d found the love my parents had—strong enough to conquer even the deep lines between social classes. That was, until I’d stumbled across the thousands of dollars she’d siphoned off me over the course of our relationship and the entire thing came crashing down.
“You’re going to have to, eventually.” What I loved about Sebastian was his stubborn persistence until it was directed at me.
“Who says?”
“I know you, James.” Sebastian leveled me with a look, his gray eyes narrowed. “You crave that kind of connection. If you don’t seek it out, it’s going to find you.”
“We’ll see about that.” I tossed a hundred dollars down on the table to cover our drinks and a tip. “Have fun tonight.”
“Always do.”
I paused in the hallway when I heard shouting on the other side of my parents’ apartment door.
The pounding of my fist echoed off the marble in the entryway foyer of their penthouse apartment on the Upper East Side. Their building’s grand windows overlooked Central Park. When I was a kid, I sometimes forgot I lived in a concrete jungle with that view. The soft hum of traffic from below barely pierced the thick walls of their upscale, meticulously decorated home. Shuffling and faint shouts came from the other side, then the door opened to reveal my mother—Eloise Rossi.
She was dressed in luxuriously simple cashmere, the kind that only a few select designers ever seemed to get right, paired with silk lounge pants. Her blonde hair was styled in a French twist, and her makeup was impeccable, not a blemish in sight. Although I got her blue eyes and high cheekbones, my dark hair and thick eyebrows came from my father’s Italian ancestry.
I wrapped my arms around my mother’s petite frame, the familiar scent of her perfume grounding me. The warmth of the hug was comforting, but something about the raised voices I’d heard from the other side of the door unsettled me. I pulled back slightly, glancing at her with a raised brow.
“What was that yelling?” I asked as soon as she opened the door. I peered over her head, unsure of what I’d find.
“Oh, it’s your father.” She waved a hand dismissively, stepping aside to let me in. “Don’t worry about it. We’ll talk later.” She was already pivoting toward the kitchen, gesturing for me to follow. “Come in. I have a snack laid out for us.”
I could tell by her calm demeanor that whatever had caused the shouting was either no big deal or something she’d seen a hundred times before. My mom had always had this ability to make things seem smaller than they were—an admirable skill, especially given how differently she and my father had been received by each other’s families when they first got together.
She’d grown up in one of those families where power and wealth were inherited, not earned. Her father had disapproved of my father for years, seeing him as little more than a blue-collar guy from a family that owned a pizza joint in Brooklyn, not someone who belonged in the same circles. But my mother had persuaded my grandfather anyway, throwing caution to the wind in a way that would’ve been unthinkable for most people of her background. Eventually, her family had come around, not wanting to lose their only daughter.
“You look good, sweetheart,” she said, steering me toward the kitchen, where she’d set out a plate of olives and prosciutto. If there was one thing Eloise Rossi loved to do, it was host. “How’s everything?”
“Good,” I said, reaching for an olive. My mind kept circling back to the shouting, but I tried to push it aside. “Dad’s alright?”
“Your uncle called.” My mother pursed her lips. “There seems to be an issue with the restaurant. Your father’s your father. He’ll calm down. Don’t worry about it.”
“What do you mean?”
She sighed, collecting another jar of olives from the pantry. “It’s the same old story. The restaurant’s in trouble again.”
I raised an eyebrow as I reached for a slice of cheese. “Trouble? What kind of trouble?”
“Your father’s family hasn’t updated anything since they built the place. They still run it the way they did back then—no website, no marketing. Just hoping people will walk in.” She shrugged as she dumped more olives out for me. “Your father thinks some changes need to be made, but your uncle always sides with your grandparents, doesn’t want to make waves.”
I nodded, having heard this song and dance before. The pizzeria had become something of a neighborhood institution over the years. But my grandparents’ reluctance to adapt to the changing times had left them struggling in a market that had long moved beyond traditional familyrun businesses.
“And Dad’s had enough of it?” I prodded, reaching for another olive.
She motioned to the plate of snacks, urging me to eat. “Let’s leave it to him to handle. He’ll figure something out. Eat first. You’re too thin. Those long hours at the office are not doing you any good.”
“I have a dinner later,” I told her, but she waved me off and edged the plate closer. I plucked yet another olive from the plate to appease her.
“What is Dad going to do?” My mother shrugged a shoulder—I wished I could strive for her level of unbothered.
“Enough talk about business. That’s all we do in this house . . . business, business, business.” She let out a long sigh before mischief filled her eyes.
“Oh, no.” I shook my head. “I know that look.”
A smile played at the corners of her lips. “I ran into Nora Lauder at brunch this morning.”
I knew this was going in a direction I would not like.
“She mentioned that her daughter, Felicity, is back in the city from her time in London.”
And there it was.
As did everyone who grew up on the Upper East Side, Felicity and I had frequented the same circles growing up—between balls, dinners, and society events. The two of us knew each other well. Which was how I knew she’d been in London for a “gap year”, even though she was years out of college. It had been more of an attempt to find an eligible bachelor overseas because Felicity Lauder had scared off nearly every man that came from a family with status. Let’s just say, “high maintenance” was a vast understatement when it came to her.
“Did she now?”
“I think you should reach out to her,” my mother continued, oblivious to my disinterest. “Ask her to lunch.”
“That’s a nice thought,” I murmured.
She reached out to wrap a hand over the top of mine. “I just want you to be happy again.”
“I am happy.” My hand turned over to squeeze hers.
“Felicity could be a great option. She comes from a wealthy family.”
“Why does that matter?” I asked. Money had never been in the conversation before with who I dated. “You didn’t marry for money.”
“No, I married for love.” My mother looked toward the study where her husband was finishing up his phone call
with the kind of adoration in her eyes that people made movies about.
My father, Giacomo, walked into the room looking much happier than I’d heard from him through the front door earlier. He walked over to give his wife a kiss, even though he’d seen her minutes ago, and reached across the counter to shake my hand.
“Well, look who finally made it home,” he said, his deep voice warm, the anger that had been audible moments before nowhere to be found.
“Hi, Dad,” I said, returning the handshake. “You okay?”
He shrugged, his demeanor shifting to something lighter. “Of course I am. Everything’s fine.”
But he couldn’t fool me. “What happened with the restaurant?”
He hesitated for a moment, glancing at my mother. “It’s the same thing again, James,” he muttered, rubbing a hand through his thick dark hair. “They’re going to run the business into the ground. I’ve been trying to get your uncle to see reason, but . . .” He trailed off, looking away.
“You both are stubborn. It’s in the Rossi blood,” my mother chimed in, not missing a beat. She moved to pour herself a glass of wine, as if this conversation was already old news to her. “The two of you are far more similar than you are different.”
I crossed my arms, leaning against the counter. “How bad is it?”
“This is the third month in a row that we’ve had to float some cash into the business to keep them out of the red,” my father said, his voice now quieter, tinged with
frustration. “I don’t know how much longer we can keep doing this.”
“I’ll help,” I said, without thinking. Both of my parents turned to look at me.
“No,” my father said quickly, shaking his head. “You’ve got your own life to worry about. We’ll figure it out.”
But I was already firm in my decision. “I can’t just ignore this. It’s been a part of this family since the fifties. You’re not going to let it fail, are you?”
He ran a hand through his hair again, clearly exhausted. “I’ll handle it.”
“I’m not going to let it fall apart, Dad. Let me help.”
My mother placed a hand on my arm. “Enough about business. It’s not good for you to get worked up.”
But I couldn’t let it go. My family’s restaurant had always been a part of our lives, and I wasn’t going to let it slip through our fingers without trying to do something about it. Despite my father’s protests, I stood my ground.
“I’ll find a way to help,” I insisted. He sighed. “Alright, but don’t say I didn’t warn you.”
I nodded, then glanced at my watch. “I’ve got to go, but we’ll talk more about this soon.”
As I headed toward the door, my father’s voice called out, a hint of pride in his tone. “It was good to see you, son. You should come around more often.”
“Think of this as a celebration for your new think piece,” Roxie whispered in my ear as we climbed the staircase of her client’s home in the Upper East Side to the kitchen, where the sounds of clinking glasses and soft conversation floated down to greet us.
Roxie looked like she belonged here.
She had pulled her dirty-blonde curls into a sleek twist that somehow made her look both editorial and effortless. Her Vivienne Westwood dress—a structured plaid number with a nipped waist and dramatic neckline— was vintage, yes, but intentional vintage. Fashion-editor vintage. She carried herself like someone who regularly dined on rooftops under string lights, not in our shared apartment where the radiator never worked properly, and the walls were thin enough to hear our neighbors’ nightly arguments.
The doorman had greeted her like she lived here. Not in the building, but in the neighborhood. Like he expected her to glide past velvet ropes and into penthouses scented with Diptyque candles and generational wealth. Like he somehow knew she drank her espresso black, owned real pearls, and knew instinctively which fork to use at a sevencourse dinner.
We’d stepped out of the cab into a part of the Upper East Side that looked like it had been airbrushed. The buildings were limestone and pre-war, with those ornate iron balconies that made it feel like Paris if Paris had hedge funds and legacy admissions. The sidewalks were unnaturally clean—like someone power-washed them every morning just in case a billionaire might stroll by.
The trees were wrapped in white twinkle lights, the kind you usually only see in wedding vision boards, and they gave the whole block this ethereal glow, like the evening had been staged just for us. Or rather, just for the people that lived on the Upper East Side. The kind who knew how to navigate a cocktail hour with charm and a touch of well-timed eye contact. The kind who didn’t flinch at coat check or get self-conscious about ordering the cheapest glass of wine on the menu.
A line of town cars idled out front, their chauffeurs leaning against the doors in crisp uniforms, talking quietly into earpieces like they were coordinating a discreet rescue mission. A woman in a camel coat walked by with a tiny dog that probably had its own monogrammed carrier and a social media following. Even her leash was designer.
The awning above the entrance was forest green, embroidered with gold script that spelled out a name I’d only ever seen in real estate listings I clicked on for fun— way past midnight, usually, when I was feeling particularly reckless. Inside, the lobby was marble and moody lighting, with a chandelier that looked like it had once belonged to someone with a title and a minor palace. A man in a tuxedo had held open the door, and I was pretty sure he’d mistaken Roxie for a socialite. Or a model. Or both.
And honestly? I didn’t blame him. Me? I’d done my best to keep up. My dress was a second-hand find from a shop in the East Village with no label and a mystery origin story. The corseted bodice hugged my waist just right, and the hem skimmed my calves in a way I hoped looked more “quiet luxury” than clearance rack. I’d paired it with the only heels I owned that didn’t destroy my feet—still not convinced I’d make it through the evening without blisters—and a clutch I’d found on deep discount at Barney’s.
I’d spent the entire cab ride rehearsing how to look like I didn’t care about fitting in—even though I did. The women here would be dripping in silk and old money, with manicures that matched their handbags. I’d curled my hair into loose waves and swiped my signature red lipstick to make up for the fact that nothing I was wearing had ever been written up in Sophisticate.
This was Roxie’s zone, despite not having grown up in this world. She lit up around rooms like this—her laughter a touch louder, her smile a little sharper. I was just hoping to make it to dessert without knocking over a glass of wine or accidentally insulting someone’s hedge fund.
“A celebration with people I don’t know who don’t know that I am writing an article on dating finance guys on Wall Street?” I lifted a perfectly filled-in eyebrow at my best friend.
“You know Michelle,” she countered. I’d been at the art gallery with Roxie on more than one occasion when Michelle Granger had come in to buy a new installation for her home or to use at a charity auction she was hosting. Michelle was one of those rare Upper East Side women
who was warm without being fake, generous without needing applause. She had a sly sense of humor that could disarm even the prickliest person, and she and Roxie hit it off immediately when Roxie sold her a ceramic piece titled Woman Smoking at Sunset and told her, with full sincerity, that it reminded her of Michelle.
Roxie smirked, her eyes gleaming with that mischievous sparkle. “And you never know—maybe there’s a hot, eligible finance guy here tonight. You could knock two birds out with one stone. You’re due for a little action,” Roxie whispered in my ear as we stepped into the kitchen, where men in Armani and women in minimalist cocktail dresses lingered around a long marble island, sipping on drinks that were being served by a bartender in a black button-down.
I couldn’t help but roll my eyes. “I’m here to write about them, not date them.”
She just grinned wider. “Same difference.” Then she took a deep breath as she prepared to blend in with the crowd. I didn’t mind her leaving me. Observing others was part of my job, and I was more than content to play the wallflower for a little while.
This was Roxie’s prime—getting to rub elbows with people in a different tax bracket than us. She could shmooze her way into a royal wedding, I was sure of it. Add a little alcohol to the mix and she could either become the life of the party or a liability—there was no in between. But she was my soul sister despite her few flaws, and there was no one I’d rather walk arm-in-arm with into a party at a mansion on the Upper East Side.
“Roxie!” Michelle swept across the room in a floor-length
black dress. Her flaming red hair shone brighter than almost all the perfectly curated art in the room. “I’m so glad you made it. Hallie, it’s lovely to see you again.”
Michelle leaned down to give me an air kiss on either cheek. I’d been around my fair share of wealthy people at Roxie’s art gallery and the double kisses would never be something I’d get used to. “Hi, Michelle.”
“Please, make yourselves comfortable. Grab a drink. Dinner will soon be served.” Michelle squeezed each of our hands. “Elliot is around here somewhere. I will make sure he says hello.”
And just like that, she disappeared back into the crowd of guests.
“Come on, let’s grab a drink,” Roxie said. Despite how much reassurance Roxie gave me or I gave myself, I could never stop that inky, black voice from sliding in from the depths of my mind to remind me that I didn’t quite fit in and would never amount to other women. Which was part of the reason I liked to avoid functions like this entirely.
Armed with a drink in my hand—part liquid courage, part social armor—I finally felt brave enough to scope out the other guests that were here tonight. Most of them were people I’d seen around the gallery or knew from the gossip tabloids. That was until my eyes locked with a pair of deep-blue eyes from across the room. Damn.
He was the definition of tall, dark, and handsome. With his long legs crossed casually at the ankles, he leaned against a kitchen counter. He’d left the top few buttons of his dress shirt undone, revealing sunkissed skin and a