Acela to the End of the Line — 4

Bad Romance

Click Here for Part 3

I woke up with a startle as the stewardess nudged me out of my sleep and gestured at me to fold my seat to the upright position, blearily surmising that my flight was one thumbing through a New Yorker bereft of content away from wheels down. The occasion was ostensibly another emerging market hunting expedition, but in reality, the past few years had mostly been restless shuffling from location to location in a vain attempt to plug the emptiness created by youthful idealism gone wrong. I signaled for one more Death in the Afternoon, a potent combination of Pernod and Ruinart, and widened my eyes so my thousand-yard-stare could catch the sunset out the window before the smog covered it up during the descent, and ruminated over the path I took to swearing off dating forever.

It all started about 9 years ago to the day, during my official gardening leave celebrating the tradition of the sell-side associate to buy-side jump, an Ivy League birthright if there was one. Although the industry term for the six-month waiting period was “gardening leave”, it felt more like my train to Greenwich had temporarily derailed — a “pause-in-the-track”, so to speak, as I associated gardening with asylum inpatients rather than career progress. Unsure of what to do with so much time off, I decided that I could best round out my personal portfolio by testing the dating market, and signed up for an “exclusive” matchmaking service where your presence alone would convey “trust fund”. When asked for my profession, I simply put “buy side”, confident that society was far enough removed from 2008 to start distinguishing ballers from bankers once again. Within 3 days, I had a few “get to know you” dates set up, which I took to mean drinks at some bar that would rob me of the better part of a 20 for a simple G&T.

The first date was with a woman I’ll call “Ladurée”, who naturally insisted that we meet in the SoHo location at 7. Of course, she didn’t check the opening hours, so by the time she arrived (15 minutes late, of course), the shop was locked up. Sensing an opportunity, I suggested we move down the street to Broome Street Bar, an old, unpretentious watering hole that, at the very least, had alcohol, as opposed to that pastel-green glorified Instagram filter of an eatery. We ordered some drinks — me, a vodka soda to imply that I watched my calorie counts, her, an appletini, as the espresso variant wasn’t a trend yet — and she asked me the question that, in Europe, would get called such an American thing to ask: “sooo what do you do for work?”

My repertoire of lines was, admittedly, limited at that point in my life. It’s cool to have a 5 sentence explanation describing what you do for work prior to 25, but not so much after. I simply defaulted to the line I’d end up repeating for the next decade when asked that question, whether it made sense or not: “I’m on the buy side.” It didn’t have to be the truth, or even meaningful — it was provocative. The word “buy” in finance always evoked the image of someone supremely confident in their own abilities and decision making. Bidding was an act of power, of sticking a flag in the ground and claiming the territory. Sell-side, on the other hand, conveyed the mentality of a door to door salesman. Much like knocking on doors to hawk products that nobody wanted, the research produced and the trades and deals pitched through “decks” that constituted “work product” evoked the aura of a teenager schlepping his way into a local smoothie shop to hand in their resume in hopes of getting a summer job because their dad refused to let them stay in the house between the hours of 9 to 5.

There was nothing else to remember about that date — over the next couple of drinks, Ladurée obviously got bored of me not asking her about her burgeoning influencer career and my internal chuckling over my buy side line again and again. The last I heard of her, years later, she had settled down with a VP in research at a former bulge bracket and taught yoga at an Equinox knock-off. When I sent a message congratulating her after her premium-mediocre wedding at the Bellagio, she replied instantly: “what can I say, some people just know how to listen.” To which I replied, “because they need to find out what we’re doing on the buy side. Where else do they get the content for their reports?”

I never heard from her again.

The second date, two days later, was with a woman I’ll call “Louis”. Not because she owned that godforsaken monogrammed Louis Vuitton purse that every woman in lower Manhattan owned, but because she had a matching phone case, a carbuncle of an accessory that essentially doubled the size of any phone unfortunate enough to be caught in it. It was that day that I discovered the nature of dating in New York — while NY airports had plenty of directs, a weekend-date was a combination of the one-stop route from nowhere, Midwest to O’Hare to make the connection to your final destination. She showed up at 5:15 (once again, 15 minutes late) to our reservation at Domo Domo’s bar for happy hour, a delightful ground-level spot which had $5 carafes of sake and $4 handrolls, and remarked that she was meeting a friend at 6:45. After two bottles of Junmai Daiginjo, she profusely apologized with practiced red-in-the-face pleasantry that conveyed an innate allergy to the prior dalliance and scrambled out to catch a cab, telling me that she “couldn’t miss” her friend who was in town “just for two days.” Imagine my surprise when I wandered into Dante, less than an hour and a half later, and saw her at a table with none other than my old roommate from sophomore year. It was then that I learned that I was the commuter flight, the pre-game, and that Trey was the flagship route for the evening. I had fun with it, of course — Trey introduced her, congratulated me on my transition, and engaged in a friendly game of credit card roulette for the next round of drinks as I joined their table. The tension was too much, however — after the drinks arrived, I took care to stare everyone in the eyes while chugging all 3 draft negronis, then walked out without saying a word. From that moment forward, I never went on a date unless I knew I was flying private.

The last date I ever went on was the last time I ever thought about the buy side. The tech rush of the 2010s was pretty similar to the gold rush, all things considered. You had a bunch of people shuffling from the East to the West, taking whatever they could with them to move to whatever role they could find, in the hope that industries built off precious metals would help them hit the jackpot that 10x’d their net worth. It was then that I discovered that the West Coasters didn’t call themselves buy siders — they called themselves angels. I had to begrudgingly give this bit of self-branding a fair amount of respect — all this spawned from an industry that was originally built by 72 virgins!

It was one of the last few days I was in New York — I was packing up before transitioning to my new role at a vertically integrated food-delivery/waste-collection startup. My flight was at 8, so I set a brunch date — a couple bloodies and a conversation at Jack’s Wife Freda would set up a proper invitation to visit our ZIRP-sponsored “campus” out in Palo Alto, where the walk-ups would never go higher than 3 stories. But as I rolled out my tried-and-true lines — “you like Huey Lewis and the News?”, “I was on the buy side, but now I’m looking for a purpose in life” — I didn’t get that doe-eyed look of awe that a Master of the Universe was accustomed to, but rather a hard stare that accompanied the words, “So what’s your TC? What’s your upside on the deal? Are you on the e-board?”

I sputtered, “Well, I’m trading my carry for a sizeable signing bonus… I’m offering 20% over ask on a condo 4 blocks away from the Stanford Campus…”

Her cheeks flushed bright red. “You’re telling me I came down from the UWS for a guy in fucking corpfin who doesn’t even touch product? You aren’t even going to be able to think about moving to Atherton in the next 5 years, are you? Can you even project an exit?”

I could feel a temper rising that hadn’t reared its head since Amazon outbid my firm on the Whole Foods deal years ago.

“Now look here, I didn’t spend a decade on the track to be treated like this. My firm supplied the initial capital for Reformation, SweetGreen, and everything else the laptop class relies on permanently. They don’t even know how to use a computer without touching a mouse! So who exactly are you to talk to me like this?”

But by that time, she had put her Birkin over her shoulder and was in the process of leaving me with the check. She sighed and clocked her vintage JLC Reverso, which, even in my perturbed state, I had to admit was gorgeous. She reached into her bag and pulled out a card.

“Here,” she said.

“If you ever figure it out, you can give me a call.”

"But wait,” I called out. “What’s your name?”

She paused by the door, turned around, and straightened her black turtleneck.

“Elizabeth,” she said, and walked out the door.

I finished my drink and turned the otherwise-blank card over.

It said, “30% Off Leetcode! Discount Code: Alpha”