We were somewhere between drink number four and five when the issue of dating landed on the table with a splat.
“If you think dating is hard, just wait ‘til you get to New York. It’s a nightmare.”
I froze, the martini suspended in front of my lips. “It can’t possibly be harder than Miami.”
“Oh, honey.”
We’ve all seen the articles. New York Ranked Worst City for Dating. Romance is Dead in the Big Apple. Sex and the City? More like Celibate in the City! But the problem with these articles is that they fail to mention each jungle has its own set of rules, a method to the madness. Every dating pool is context-dependent: it favors some and disfavor others, something I first noticed when I lived in Miami.
Four years into my Miami residency, my worst nightmare became true on a fine Thursday night during wine night: everyone in my friend group, comprised of six good-looking girls, had acquired boyfriends except for me. I was officially the Last Woman Standing. And if you’re a girl reading this, you know that’s the absolute worst thing that can happen to you. Suddenly it’s the One Musketeer and the phrase “thick as thieves” means complete and utter shit. And in a city like Miami, where a Friday night can easily suck 1k out of you like an experienced hooker, hanging out in the single digits isn’t exactly financially responsible. Especially for a girl in her twenties working an entry-level job in Marketing.
Yes, Marketing. In this economy.
My first Friday as the Last Woman Standing arrived and I refused to sit still. I donned my tightest, shortest, and sluttiest, and walked out of my beachfront apartment in stripper heels. By stripper heels, I mean those transparent kitten heels I often use when my bank account’s feeling thin and I need to pull a miracle over the weekend. I drove myself out to Joia Beach, a beachfront restaurant in Jungle Island, and landed on one of the tables by the water with a book in hand. Not just any book, but Lyrical and Critical Essays by Albert Camus. If you ever want to have a smart conversation but have no one with a respectable IQ to chat with, just pick up that book and you’re all set. It’s a collection of essays and interviews where Camus just… chats. About anything, and everything. I opened the book on a random page and landed on The Wind At Djemila.
There are places where the mind dies so that a truth, which is its very denial, may be born. When I went to Djemila, there was wind and sun…
“What can I get you, gorgeous?”
I looked up and recognized Manu, the waiter we always got at Joia Beach. I grinned, “The usual, please.”
He nodded. “Martini coming right up. By the way, Val...” He scratched his jaw with pink nails, plucked eyebrows raised. “Why are you reading? Are your friends on their way?”
We’d hung out enough times at Joia to be on a first-name basis with everyone there. I slowly stopped smiling. “Ah, no. They all got boyfriends. It’s just me tonight.”
“Que? No me digas eso, con lo bella que eres tu?”
“Que te puedo decir, miji.” I shrugged. “It’s fine, maybe I’ll meet someone tonight.”
He raised an eyebrow, the same way a grandma does when she hears something sus. “With that book, you’re just gonna shoo them all away. El mesonero de alla te llamo la espanta hombres.”
I rolled my eyes. “Aja y que quieres que haga? A quien le hablo?”
“Ay, yo nose, chama.” He popped a hip, pencil tapping on his notepad. “I’m getting you that drink, you’re gonna need it.”
By the end of The Wind At Djemila and my second martini, I looked up and caught a group of men frowning at me from another table. I frowned back, and would’ve barked at them if I’d been on martini number four. Manu brought yet another drink, and still not one person approached me. I looked down at myself—I knew I looked good. I’d done Ozempic for the first time, so I was half my usual weight, and I had my period so my boobs were twice their normal size. Make-up? On point. Hair? IGK-verified. Dress? Whore-ish.
O-kay. Fine. I closed the man-repelling book and walked over to the bar, climbed up a stool, placed my bag on the counter, then hid the book beneath my crossed legs.
Not five minutes passed when the woman next to me started chatting. Her name was Barbara; she was a real estate agent with long, black hair and stone-hard 32-D boobs. Next to her was her husband, whom she introduced as Jeff, and whose baldness shone brighter than the full moon hanging from the sky.
“Actually, my husband and I were just talking about how beautiful you are. And we um, we’d like to propose something to you.” A devilish smile slowly slithered up her face.
I slammed my drink down on the table, the single olive spinning. “Jesus fucking Christ, seriously?” I hopped off the stool and made my way back to the car. Defeated, and friendless.
As soon as I got home, I searched Book clubs near me.

By the end of my fifth year in Miami, I decided to relocate to New York and pursue my dreams of being a writer (jajaj). I’d gotten a promotion at my corporate job (the one that pays the bills) with the one condition that I moved to New York and, if you’ve lived in Miami for longer than a year, I’m sure you know exactly how desperate I sounded when I accepted the offer.
My last Friday in Miami was spent at Monterrey Bar, the speakeasy at The Standard where every martini is well-above $24 but lower in temperature than most cold plunges in South Beach. I sat down with my friends, some of them ex-New Yorkers, and began peppering them with questions about my new home.
“If you think dating is hard, just wait ‘til you get to New York. It’s a nightmare.”
“It can’t possibly be harder than Miami.”
“Oh, honey.”
I landed in New York on a cold Sunday night in January. The city was blanketed under a thick layer of snow and, from my window seat, I quickly found my new building on the edge of Seaport. I went to work on Monday morning, had a mental breakdown on Wednesday when all the furniture arrived from Miami in broken boxes, and by Friday night I’d lost my work badge, the only scarf I owned, the keys to my new home, and a good chunk of my dignity.
Drunk, cold, and clad in a mini dress that did nothing to shield me from, well, anything, I began banging on the door of my new building sometime around midnight. My building, nestled between Dover Street and Peck Slip, had a front desk that was either in the bathroom or asleep behind his desk. Regardless of what he was doing, I desperately needed someone to open the door.
A few minutes passed before I banged again. Shivered. A bike sped past behind me, the sound of the bell quickly growing distant. Cold seeped into my bones as if they were made of paper towels. Laughter echoed. I looked around, my surroundings fuzzy and unfamiliar. I noticed, for the first time, the amount of abandoned furniture on the corner. Mhm. I grabbed one of the stools and placed it right in front of the front door. I banged the door again, harder.
“Sheesh, woman, you’re gonna break the door.”
I turned around and found a man standing a few feet away with his hands in his pockets. He was completely drenched, his blue button up sticking to his skin, breath clouding in front of his face.
“That’s the goal, at this point.” I mumbled, then dismissed him and banged again. A few seconds ticked. Bang.
Laughter emanated from behind me. I’d assumed he’d left, but found him on the same spot, teeth chattering.
“You could stay here and wait, or," He paused. "You could get a drink with me and try again in a bit.”
I turned around and actually looked at him. He was about my age, maybe a few years older. He had a piercing on his right ear, and rows of rings in every single finger. His wet shirt stuck to him like a second skin, and I could see his—
“Wait, you’re freezing.”
“Well, yes.” He grinned, a dimple materializing. “You’re freezing too.”
“But you’re wet. Why are you wet?”
“Why are you wearing that in this weather?”
I glared. He glared back, then sighed.
“I was on a Citi Bike in the middle of the Brooklyn Bridge when it started raining. Nothing I could do but ride it out.” He rubbed his hands up and down his arms as he did a little dance side to side. “Sooooo, drinks?”
His name was Tom, and he lived in the building right behind mine.
We shook hands and walked to the next block where we landed in front of a black wall. I raised an eyebrow as I looked around. There wasn’t a single window or door in that entire block; it was just one long, black wall.
“Is this when you murder me and sell my organs? ‘Cause my liver isn’t exactly at its prime.” I paused. “Nor my lungs.” Longer pause. “Nothing in here’s at its prime, really.”
“Nah, too messy.” He crouched and grabbed a golden knob from the ground, pushed it into a hole I hadn’t noticed before, turned it clockwise, and pushed an invisible door wide open. Inside, there was a world of lights, music, and laughter you would’ve never thought waited behind that wall in the quietest street in Seaport.
“Tommy boy! Come on in!”
Christmas lights of all colors crisscrossed the ceiling from beginning to end, and to the right there was a long bar covering the entirety of the room, with bottles of everything spanning the floor-to-ceiling shelves. Behind the bar, one of the bartenders was slinging drinks in a metallic-purple shirt that was far too tight for his belly.
“Vinnie, good to see ya.” Tom slapped Vinnie’s shoulder like all men do by way of greeting, and pushed one of the two empty stools towards me. “This is Val, she just moved across the street.”
“Water Street?” Vinnie asked.
“Front Street.” I smiled.
“Ah, we don’t have a friend in that street. But now we do!” He grabbed a bottle from beneath the counter and placed it in front of us, dark-brown liquid sloshing, then placed three shot glasses next to it. "To new friends!”
“To new friends.” I mumbled shyly, then downed the shot and crunched my face immediately. Rum. I hated rum.
“You’ll get used to it. Alright, let's introduce you to some people, shall we.” Tom patted me on the back before grabbing my hand and yanking me across the bar.
“This is Molly, she lives above Peck Slip and has five cats. Not four, five.”
“Shannon, my landlord, lovely lady.”
“This is Mike. Did you ever watch The Wiggles? He used to be the red Wiggle.”
“See that guy with the pink buzzcut? He’s the bartender at the bar next to your building. Yeah, no, that’s not a market, there’s a bar in the back.”
“That’s Rob.”
“This is Lorena, hi Lorena!”
“Have you met Shannon already?”
Thirty minutes and fifty new names later, I plopped down on the stool once again and exhaled in relief. “I fear my social battery is fried.”
“You’ll get used to it.” Tom smiled as he poured us two shots from the bottle Vince left behind. “Salud.”
“Salud.” I clinked my glass with his then downed it. The rum didn’t taste so bad anymore.
“How did you meet all these people?”
“Gradually, then suddenly.”
I frowned. “Really.”
“I’m serious! I met them just hanging around the local spots. Eventually you cross paths enough times for the names to start sticking. People are very open in New York, contrary to what most everyone thinks.”
“What about this place? I don’t see a name out front.”
“Think of this as the community club. Remember Mike? The red Wiggle?”
I nodded.
“Well, he technically owns the space, but he doesn’t manage the bar itself. The locals work here sometimes and help run the bar, and we all pitch in when the money’s low. Take Vinnie, for example. You think he’s an actual bartender?”
Behind the bar, Vinnie was pouring three bottles of something into one plastic cup, the resulting liquid a strange shade of brown. He sniffed it, cringed, nodded, then handed it over to the girl in front of him. I shook my head no.
“He’s a software engineer who works from home and plays bartender when he’s bored.” Tom chuckled, reaching over the bar to grab two beers from the ice box, then handed me one. “If you ever wanna give bartending a try, just tell Mike or Shannon and they’ll give you a set of keys.”
I frowned. “I’m a complete stranger, they’re not gonna give me a key.”
He shook his head with a strange smile on his face. A smile that said something around you’re not getting it. “We’re all strangers in this city, until we’re not.”
I left the bar around 3 a.m. with a dumb smile on my face, the cold no longer making me shiver. I plugged in my earphones, hit play on a Frank Sinatra song, and waltzed back home with about fifteen new names in my contact list, the city lights twinkling just for me. The front desk man smiled and waved at me from behind the door, then buzzed me in with an apology and a new set of keys (which I also lost.)
Tom became my friend, and I’ve met a whole new set of people through him and the Seaport locals. At the book clubs I joined, I’ve made friends that don’t have the same perspectives I do, nor the same age, nor the same background. Now I know how ignorant I am about things such as Ramadan or Yom Kippur; I’ve been to pocha bars with my new Korean friends, and I’ve tried actual Bengali food with Bengali friends. Now I have friends whose parents are janitors, billionaires, housemaids, housewives.
My experience of Miami is very Latin American, but also very homogenous in terms of financial background and customs. Most of the people I surrounded myself with looked and thought and dressed and drank and dated and lived the same way I did. They were also mostly girls (have you noticed that, at Latin parties, the women go to one side and the men migrate to the other? No? Sure.) In Miami, the conversations sounded the exact same weekend after weekend. Think of it as a fishpond: When you exist in stagnant waters where nutrients are scarce, the fish eventually stop growing. We become small minded when we surround ourselves exclusively with what’s known, especially during formative years.
I don’t think one city is better than the other when it comes to dating, but I do think New York, a city where you’re allowed to start as a stranger, opens itself for dating a whole lot more. Being a complete stranger in Miami means you probably didn’t belong to some sort of society (what people refer to as “gente bien”) back in your home country, so starting from scratch is a lot harder. In New York, you’re allowed to be born again, and again, and again. You meet new strangers every day, and you get to tell your own story multiple times, which also allows you to learn about yourself through the eyes of another person, another culture, another life.
The worst city for dating is not the one where people are busy, or the cost of living is high, or the percentage of singles is low. The worst city for dating is the city that doesn’t encourage personal, emotional, or intellectual growth. It’s any city you’re in, if you’re not learning new things, and meeting different people, and experiencing things for the first time.
There are places where the mind dies so that a truth, which is its very denial, may be born.
When I went to New York, there was sunshine and moonlight…