My Year of Finance Boys


First Person

Sg1959, CC BY-SA 4.0, via Wikimedia Commons.

I shouldn’t have been surprised that the hedge fund analyst knew me better than I knew myself. It was his job to predict distant developments, covert motives, hidden risks, and shortly into our brief relationship he turned his powers of divination on me. After I told him I was writing a novel about finance, he suggested that I’d been drawn to him partly for mercenary reasons: that I was, in a word, dating him for research. He took it in stride—he lived and breathed all things mercenary—but he did issue a polite warning.

“Never put anything I tell you in writing,” he said.

I’d like to think that, in his predictive genius, he also knew I would eventually ignore this warning.


The hedge fund analyst, whom I’ll call Jake, was the last in a string of finance boys I dated during a peculiar if productive period of my life. Almost as soon as I’d embarked on my novel about finance, I’d begun scanning dating apps for Patagonia vests and Barbour jackets. I wanted investment bankers, private equity associates, traders. I maintain that my motives were not as Machiavellian as Jake would go on to imply. I’d decided my novel would treat the technicalities of finance lightly, and I was already doing research sufficient to my purposes: auditing finance classes at the university where I was a graduate student, reading textbooks, conducting interviews. But Jake was probably right that my creative and libidinal impulses became, for a time, precariously interfused.

My interest in finance men as romantic material was as mysterious to me as my interest in finance as material for a book. I’d never earned enough for money to be anything but a source of panic. I had no idea what a derivative was and thought bear and bull meant the same thing. The distinction between a 401(k) and a Roth IRA was lost on me and in any case irrelevant because I had neither. And yet at some point during my years in New York, I became curious about the world of finance, then dazzled by it, and then—as my interest concentrated itself on the men who operated its levers—transfixed. Maybe the political convulsions of 2016 had awakened my class consciousness and spurred me to learn more about the people who shuffled the world’s capital. Maybe, as I neared thirty, I’d grown tired of financial precarity and subconsciously begun a search for a mate who would ease my misery. Maybe I saw in these men an obscure point of recognition. All I knew was that my curiosity would persist until I satisfied it.

There was no shortage of finance guys on my dating apps of choice, and they made themselves readily discoverable. On Tinder, Bumble, and Hinge, they often cited their employers and alma maters, and the moment I saw “Deutsche” or “Wharton” I swiped right. But even on Grindr, where a profile might be limited to a single mirror shot and a headline reading “Hung vers,” they were easy to spot—they had a signature, beguiling blandness. As I studied their neat haircuts and plain handsome faces, as I read their hyperminimalist messages (“Good u”; “Not much”) and inspected their skimpy bios (a Statue of Liberty emoji, a weightlifting emoji, sometimes a string of airport codes and accompanying travel dates), I tried to imagine my way into their evocatively dull lives. Seventy hours a week spent at a trading desk absorbing cold light and thin filtered air, lunch at Sweetgreen or maybe Dig, an interlude of bench presses and selfie replenishments at Equinox, dinner with the Bowdoin ’08 crew at Westville, an hour lying in bed messaging with the likes of me, then porn, then sleep. For reasons mysterious to me I thrilled to the idea of this moneyed monotony. I swiped some more. I asked when they were free.

On my very first outing, I had the fortune or misfortune to have many of my preconceptions confirmed. His name was Andrew, he worked at Goldman Sachs, and he was, to my jubilation, supremely boring. He’d gone to prep school in New England and college in California and now lived with roommates in the West Village, though he had his eye on a one-bedroom in a glass monstrosity in Tribeca. He was tallish, blond, inconspicuously good-looking, and responsibly dressed: the kind of person who lives in your memory only as a pleasing, gleaming outline, devoid of eyes.

He described his life in a white-noise murmur. He told me about a presentation deck he’d recently been tasked with putting together. He told me about the challenge of assessing new markets. He told me about his fraternity days, his weeks on Fire Island. He told me about his life’s dream. He wanted to clamber up the ranks of investment banking, he explained, and then start a company of his own. “I went to the Harvard of California, and now I’m at the Harvard of finance,” he said. “I want to do something unexpected.”

We were well into our second drink before it dawned on me that our date was not going especially well, and that we would almost certainly not meet again. I alighted upon this fact as if returning to the present, which raised the question of where I’d been. Andrew probably wondered the same thing. I’d mostly smiled at him and said little. I can’t imagine that I was emitting palpable pheromones. My interest in him was intense, but it was strange and abstracted, and very likely he saw me as a strange and abstracted person. But this didn’t bother me, and the fact that it didn’t bother me offered me the first clue as to the utter bizarreness of my experiment. I didn’t want to date these men, or at least not Andrew; I simply wanted to soak in their flavorless presence. I’d conjured a fantasy of a finance boy, and here he was, in the flesh, as radiantly banal and enthrallingly uninteresting as I’d expected him to be. I felt as if I were staring into a void whose howling depths could power not just one novel but a hundred.

After we said goodbye, I walked for a while through Midtown, staring up at the kind of corporate towers in which I imagined my fantasy finance boys worked. Everything in my aesthetic education had taught me to find these buildings ugly. They were cold, faceless, feats of commanding presence that conveyed nothing so much as absence, nullity given form and made brilliant. The more I stared up at them, the more I saw in their synthetic, frictionless surfaces echoes of Andrew’s synthetic, frictionless life, and the more I understood the novelistic challenge before me. I might be enchanted by the void I’d sensed in Andrew, I might be tickled by the idea of being such a vacuum myself, but a vacuum wouldn’t carry a novel. How to imbue an outwardly dull person with vibrancy? How to locate color and flair in a life of hollowness and obliterative efficiency? Why should a reader be interested in these finance boys? Why was I interested? I went back into the field.

There followed several months of what Jake would go on to call research. I had a fling with a former investment banker who now operated an Airbnb business that appeared to be illegal. I had a fling with an M.B.A. student who went to great pains to deepen his voice and who once showed up to my apartment at midnight with a twenty-ounce coffee. I had a fling with a McKinsey consultant who fired off work emails during our dates and who, I’m pretty sure, decided to break things off after he noticed that my bathroom ceiling was covered in mildew. I had a fling with a veep at Morgan Stanley who ended his days by watching My 600 lb. Life.

In each of these men I saw the same enigma. Something about their jobs seemed to have drained them of personality, blunted their curiosity, thinned out their speech, as if the drama of being a person had been shrunk to a matter of market efficiency, as if after thousands of hours of sitting in conference rooms and hunching before Bloomberg terminals they’d mistaken their spreadsheets, pitch books, white papers, and cash flow statements for materials out of which to assemble a soul. It didn’t occur to me then to wonder if I might be projecting this blankness onto them, or to wonder what purposes of my own such a projection might serve. All I told myself was that I had to go further. I went back on the apps. And then I met Jake.

On our first date he took me to a “speakeasy” in the Village, and I put that word in quotes because the whole bar was in quotes: conspicuously nondescript entrance, bartenders dressed in vaguely steampunk outfits pouring ingredients from brown glass medicine bottles, hazardously dim lights and lurid red accents meant to evoke, I supposed, the glamour of Prohibition. Jake bought us drinks and asked about my life with a clipped precision that made me feel as if I were sitting for a first-round interview. I waited for his eyes to glaze over at the mention of my writing, but to my surprise he listened attentively.

“I love that,” he said. “That’s fascinating.”

I shrugged. “You sit at a desk and type,” I said. “It’s all in your head. From the outside, there’s really not much romance.”

Jake had gone to law school and put in a few years at a corporate firm, but he’d soon left for his current hedge fund, believing finance to be infinitely more engaging than the law. He loved ideas. He was delighted to be on a date with a fellow “intellectual.” He was hungry for book recommendations, though it became clear that his literary tastes tended toward the subgenre of TEDx: Daniel Kahneman, Nassim Nicholas Taleb, Yuval Noah Harari. And yet of all the finance boys I’d gone on dates with, Jake presented the most serious challenge to my preconceptions. He had a fitful, furtive, vaguely paranoiac demeanor, and the more he drank, the more his eyes shone with a searching, apprehensive need. He was a person, in other words, intensely so. Three hours later we were back at his apartment.

All evening Jake had courteously answered my questions about his work, but now he deflected. He didn’t want to work in finance forever, he said. He’d organized his life according to a program of delayed gratification. He’d opted for an “inexpensive” apartment ($1,800 a month) so that he could focus on paying down his law school loans and funding his 401(k). He hoped to land enough sensational deals now to obviate the need for full-time employment and pave the way for an early semiretirement. He opened his laptop and showed me a dream house he’d recently spotted on Zillow: a glass-and-concrete mansion perched on a bluff in the Rocky Mountains that was going for $26 million. The house wasn’t to my taste—it seemed like the home of a Dracula decked out in Patagonia—but I certainly understood the fantasy. I too entertained scenarios in which I sold a book for a mint and escaped to some beautiful, terminal destination: a place whose austerity would complement the austere labor, the unromantic sitting and typing, that had gotten me there; a place whose solitude would give outward form to the solitary headspace in which I worked; a place where I could assume what I suspected was my natural state and be alone.

Jake shut the laptop and looked at me with daunting candor. “I’ll see you again,” he said, “right?”

I knew at once that Jake was asking of me something more complicated than I’d been prepared to give to any of my other finance boys, and for a moment I hesitated. But then I said yes, and when he asked me the same question after our next date I said yes again, and by the end of the month he was calling me his boyfriend.

I enjoyed having a “hedge fund boyfriend.” I told my writer friends about him and luxuriated in their reaction, a pleasing mixture of disgust and titillation. I thought about him while I sat writing alone in my room, and the mere fact of my connection to him, to his scrubbed professionalism and lofty salary, seemed to take the sting out of the bleakest aspects of my life: the mice that were forever darting out from under my kitchen cabinets, the roaches that were forever scurrying out from under my drying rack, the money that was forever disappearing from my checking account. When I walked through the city with Jake at my side the corporate buildings overhead seemed less alien. I felt like a participant in their ugly force in a way that I never had before. I besieged Jake with questions. I looted his bookshelves for finance explainers and investing guides and took notes. I studied his clothes and replicated his drink orders. I felt buoyant, like I’d stepped outside of myself, into that zone of nonself where, as a fiction writer, I most loved to be. If I never took the gradations of our relationship too seriously, it was because I never thought of myself as doing anything other than playing.

Very soon, however, Jake and I encountered our first point of friction. Jake liked to go to upscale restaurants, but he did not, despite his awareness of the vast difference between our incomes, believe he should pay for me. Between my graduate teaching stipend and my freelance work I made about $40,000 a year. I couldn’t keep dropping seventy-five dollars every time we went out to dinner.

“I’m wondering,” I said to him one night, “if maybe we can introduce some variety into our hangouts?”

Jake looked at me, all curiosity.

“Maybe we don’t always have to go out to dinner?” I said.

“What would you like to do instead?”

“Maybe we could eat more casually?”

The light of understanding shone in his face. “It’s too expensive,” he said.


He nodded. “I’ve actually been thinking,” he said, “that dating you could have an incidental benefit for me. I’ve been trying to spend less money anyway.”

A chill settled on my skin. I didn’t love the idea of my poverty being an “incidental benefit,” but I’d been reading his books, writing down things he said, clocking his mannerisms and persuasions. I was aware that dating him had an “incidental benefit” for me too—and that in my case this benefit might in fact be the primary one—so I said nothing.

“Tonight,” he said, “we’ll go somewhere cheaper.”

Somewhere cheaper turned out to be the restaurant extension of a famous cheese shop. No single item on the menu was in itself particularly expensive, but the dining approach was “small plates,” and by the end of the meal I’d been confirmed in a long-held theory: that there is no class enemy more fearsome than a restaurant serving “small plates.” My half of the bill: seventy-five dollars.

There emerged other points of friction. On any given night Jake drank enough for three people, and keeping up with him had put me in a state of perpetual hangover. Our sexual chemistry, never robust, soon waned. Jake also took it for granted that he was smarter than me, which I didn’t mind; in many respects he was. But I’d grown tired of his habit of subjecting me to longueurs about behavioral theory and defenses of his centrist politics. His grinding work stress often thrilled me, from a novelistic standpoint as well as an erotic one, but at times it could be genuinely disturbing. One night before going to sleep he saw a belittling email from his boss—from what I could tell, it either concluded with or consisted entirely of the words “Google it”—and immediately he got out of bed to draft a reply. I told him to wait until the next day, but he ignored me, and when I got up to pee at four in the morning he was still out in the living room, in his underwear with the lights on, staring at his phone.

By far the biggest difficulty, though, was our growing mutual awareness that Jake cared about the relationship much more than I did. When his parents came to town he told me he wanted me to meet them; I gently declined. He proposed trips we could take together; I brushed him off. The more time we spent together, the more glaring the imbalance became. He looked at me moonily, pawed at me puppyishly, made abortive efforts to engage me in conversation. But I was cold and I was only getting colder. I’d withdrawn from him at some point, disappeared somewhere, and he was struggling to pull me back.

The problem, I knew, was that my writing was finally going well. The time I’d spent immersing myself in the lives of my finance boys had unlocked something. I’d landed on a vocabulary, a pitch, a momentum by which I could transform my rough outline and inchoate ideas into a living, breathing document. I woke up each morning in my apartment eager to get to my desk. All my energy, my attention, my interest and lust for life were reserved for those hours in front of my laptop. I somnambulated through my meetings with students, my dinners with friends, my nights with Jake. I was happy, and to protect my happiness I presented the world with a flatness of expression not unlike that of so many of my finance boys. What I’d said to Jake on our first date was true. It’s all in your head.

It was in this state of contented disengagement that I met up with Jake on what would turn out to be one of our last nights together. We went to dinner with a friend of his from law school. The friend was cheerful, animated, solicitous: he seemed to detect the frigidness between Jake and me and did what he could to inject the evening with warmth. But I looked at the menu and saw the same preposterous prices. I listened to Jake hold forth on various topics with the same heedless, patronizing egoism. I looked out the window and envied the passersby. I knew it then: the experiment was over.

When we returned to his apartment Jake and I had our first full-on fight. I don’t recall the particulars, but it was essentially a recapitulation of my familiar complaints—yet again he’d talked over me, yet again he’d shown insensivity by taking me to a restaurant beyond my reach. But even I knew my grievances were arbitrary, disconnected almost totally from the base truth: I’d lost interest in him.

He apologized, defended himself, apologized, defended himself, but the more he talked, the more he seemed to see the conversation’s futility. Eventually he put his face in his hands, bent forward, and began to sob. His crying had a programmatic, theatrical quality, and I suspected that he was simply pretending, that if I pried his hands from his face I’d see no tears. But this did nothing to diminish my pity. Fictional tears are no less desperate than real ones; pretending has a sadness all its own. If my time as a fiction writer, if my year of play-dating finance boys, had taught me nothing else it had taught me this.

I should mention here that the reason Jake and I had gone out to dinner was that it was his birthday.


Our parting was amicable. We agreed to remain friends. Jake said he hoped he could still bother me for book recommendations, and I said I’d be disappointed if he didn’t. But a few days later, after the pangs of nostalgia and regret had largely abated, I returned—with a deliberation that enlivened me but had also begun to frighten me—to my novel.

I wrote ferociously, developing a plot around a finance student who flunks out of investment banking in part because of the weight of his imposter syndrome and his stubborn self-alienation—his inability to square the performance of a self with the work of being a real human being. Yes I was interested in capitalism, in class, in money’s outsize role in politics, and yes these were serving as the thematic buttresses for my book. But my fascination went deeper, and now I looked it in its strange face. The hollowness I’d sensed in my finance boys, I saw, that I’d sometimes invented where it didn’t exist, was really my own. And the emptiness I’d attributed to the world of finance was really the emptiness of the world I knew best.

In Jake’s mind the life of a writer had a color, a vibrancy, a flair. But to me it was an almost inhumanly cold endeavor, and I treasured it not despite but because of this. I never felt freer, never more powerful, than when I was hovering in the thin ether of pure sentience, a nonself in a nonplace, driving my characters to delight and destruction, orchestrating their financial ruins and romantic paroxysms from the safety of my anonymous omniscient perch. I thought of my time in that nonplace as my “real life,” and when I was in the grip of it I had little to offer the three-dimensional world or the people around me. The book, I knew, would take years to finish, and I resigned myself happily to an extended stay in that zone of detachment. Why I craved this detachment, and whether my desire for it was the cause or the effect of my decision to be a writer, were questions I couldn’t then answer, and still can’t.


Almost exactly a year after our breakup Jake surprised me with a text: Would I come to his birthday party? I hadn’t spoken to him in months, and I’d quit my habit of seeking out men in the field. But I’d be lying if I said I didn’t still harbor some residual curiosity. I imagined the crowd, felt my skin tingle, and said yes.

Jake had since moved to a freshly constructed tower in Midtown that, from the street, I would have taken for an office building. I rode the elevator to the top-floor event space he’d reserved, hung my jacket on a rack, and walked into a room that looked like a vast operating theater. Double-height ceilings, blinding white walls, lights so bright I found myself squinting. The crowd was modest but respectable: thirty or forty people, some standing by the floor-to-ceiling windows, others queuing at the bar, where two shirtless muscle boys poured drinks. I spotted Jake, but he was holding court among friends, gesticulating wildly to titters of delight, and I decided to visit the bar.

There I ran into Jake’s law school friend, who caught me up on everything I’d missed. Apparently at some point in the past year Jake had become very rich. I assumed some phenomenal deal had gone through. “We used to be at the same level,” the friend said, “but now—now.”

Once I’d retrieved my drink the friend guided me toward a circle of very tall, very beautiful gay men. To judge by the Teflon sheen of their faces every one of them had undergone Botox. They introduced themselves and then promptly resumed their conversation, which concerned shoes. They took turns placing their feet at the center of the circle and basking in remarks of approval. I looked back at Jake, but he was still regaling his friends. I heard one of the beautiful men say “Bottega Veneta” and walked away.

At the far end of the room, glass doors gave out onto a terrace. When I stepped into the fresh air I saw that the swiftly dropping temperature had kept everyone else inside: the lounge chairs were empty, the railing clear. I walked to the edge and laughed at myself for coming. I was several tax brackets beneath the next-poorest person here; I was an ex a few years away from being forgotten. But as I looked out at the city, twinkling beneath me like the disgorged contents of a great jewelry box, I felt a familiar, transcendent, dissociative sense of play. No one here except for Jake and the law school friend knew anything about me. I was as inconspicuously good-looking and responsibly dressed as anyone else. I could easily pass for an investment banker, a private equity associate, a trader: a presence that conveyed nothing so much as absence. The breeze quickened, my teeth chattered; I felt weightless and dizzy. Always playing, hiding, playing, hiding. After a few minutes I went back inside and made to leave.

When I approached the coat rack, however, I was presented with an unexpected obstacle. For Christmas I’d asked my parents for a Barbour jacket. Apparently my time performing a self—any self—was far from over. The obstacle was this: there were several other Barbour jackets hanging on the rack, all the same shade of dark green. I had to dig in several pockets before I could identify mine.


Daniel Lefferts is a writer living in the Hudson Valley. His debut novel, Ways and Means, was published by Abrams/Overlook in February.