The Last City I Loved: New York


I liked the place; I liked the idea of the place, was in a fortune cookie I once ate while living in New York.

It’s understandable that some people move to New York, give it three months, hate the fuck out of it, and move back to where they came from. This happens all the time. How could they not hate it? It’s so hate-able. It’s disgusting. It’s filled with shit and piss.

But then there’s the other side, when the piss and shit meets your needs. That was my side.

Love at first inhale.

I love Manhattan. Always have. My mother tells me that when she brought me to New York as a little girl, I would climb the steps out of the subway station and when I reached the top, I’d moan with pleasure, and say, “I loooooooooove it here!” My dad tells me that on the subway when I was four or five, I walked up to a young woman who was wearing black nail polish, black lipstick and black eye-makeup. I stared, amazed—five inches away from her face.

The first time I moved to New York, It was June, and my mother drove and dropped me off in Williamsburg at my brother’s apartment. I put my pink and white polka-dot sheets on my bed and my brother made me a key and that was that. It down poured and I was so joyous that I was calm. In my journal, I wrote: The past three days have been, well, magical. It stands out in my mind as the time when I was in exactly the right place at the right time.

The first thing I did was lay down on a canvas bigger than myself, which was hanging around the apartment, and have my roommate outline my body. Then I tore up tiny pieces of colored paper and worked on filling in the whole thing with bright pink, purple, orange and yellow pieces of paper. It was a mosaic of a rainbow. It took me months to fill even a quarter of it up.

Five blocks down the street from me was Fix Café. Fix was dark and dreary and large, with torn couches and a piano. Fix served coffee and alcohol all day, and hardly any food. I’d just turned twenty, but the black haired barista/bartender served me alcohol anyway. Once I figured this out, I returned every day, when I got out of work at my own job at a café a few blocks away. I was off work at three, and that’s when this bartender/barista began her shift at Fix, changing it over from the day place and getting ready for the night. When I walked in, she’d light up, and say, “Hiiiiiiiii, little one.” Her name was Angelica, and she was twenty-five. I sat with her and she talked to me while she bleached the counters and sliced lemons and limes.

Angelica had lived in Williamsburg for years and wouldn’t walk down Bedford Avenue without wearing sunglasses, for fear of running into someone. But we always ran into twenty-nine people anyway. She was an Oakland transplant, an alcoholic with a cocaine addiction and she took me under her wing. “I love my little baby Chloe!” she’d announce at the bar when she emerged from the bathroom where she’d been doing lines. Then she would blast the song “Danger! High Voltage” by Electric Six and dance her ass off. Late at night, she’d lock the door to the bar, kicking everyone out except for me and maybe another friend or two on the stools. She’d put the song “Seventeen” by Stevie Nicks on her iPod. One of her favorite things to do was point at me and sing the lyric: “I’m a few years older than you… (I’m a few years OLDER than you)” making everyone at the bar laugh. Then she’d hand me a twenty and send me to the deli to buy her some Sparks to drink. She liked being older than me and I liked her being older than me. We adored one another.

I didn’t move to New York with a computer, so I used my brother’s sometimes. One morning, during my first month in New York, I was signing into my email, and saw something he’d written to a friend about how he liked Brooklyn but wanted to get more in on the scene:

But it looks like my sister’s doing that for me. She’s only been here a week and already befriended Williamsburg’s indie guru, Angelica, who knows all the bands.

The first time Angelica asked me to hang out with her outside of the bar; I thought she was pulling a prank. She asked me to go “flyering” with her, (a word I’d never heard before) and I asked her five times, “So, 7 p.m.? Meet you on the corner of Bedford and North 11th? That’s where we’re meeting?” until she was looking at me like I had four heads. I thought it was some kind of joke—like she was going to stand me up.

But she didn’t. We stayed friends for years.

Many winter week nights, around midnight, when I was getting ready to go to bed, my cell phone would ring. Angelica.

“I’m outside your apartment. Do you want to get Stevie?”

She spoke this in the California drawl that she had, and it was very difficult to turn her down. Turning her down would be missing out. “Stevie” was what she called cocaine.

I’d throw on clothes and tell my brother I’d be back. Angelica was usually dressed in all black, wearing cleats on her feet, turquoise rings on seven out of ten fingers, and three necklaces with vintage owls hanging on her chest. She’d be holding a coffee cup filled with vodka or gin. We’d walk to Union Pool and Clem’s and Savalas. She knew everyone, and could get me into the bars just by being charming and saying, “This is my friend Chloe, she’s goooooooooood,” and the guys at the door would always let me through without any ID. Angelica often left me on my own at those bars, introducing me to people with names like Treb, Bo-Bo, and Sisqo, and then going off into the crowd. We’d lose each other for what seemed like hours. This was really great for my social skills and not so great for my social smoking. I met a ton of people I’d never be long-term friends with, but sitting on those barstools, or in booths, or outside on a patio around a fire, made me feel part of something enormous. At four or five in the morning, I’d tell her I just had to get home, and I’d walk back to my apartment, stumble in, my brother long sleeping. She always made me call her to tell her I was home safe.

When I think about my first year in New York, Angelica is what I see. We were always together. We bought hard boiled eggs and pickles and Chinese food and cocaine together. We played the card game “Spit” at bars for hours. We ate chocolate and read our horoscopes in the Village Voice. We were both fire signs. She poured Black Boss beer on her head and told me I had to be more ultimate. “You just gotta be more ullllllllltimate… like this!” she said, drenching herself in beer. Angelica had an on and off relationship with a member of TV on the Radio. She introduced me to bands: Grizzly Bear, Dragons of Zynth, Miles Benjamin Anthony Robinson and the Castanets. She shoplifted from American Apparel. She wore gold lame pants. She hated Devendra Banhart and loved Bell X1. She disliked all of the other friends I would come to make and told me so.

Can I get through this essay without referencing Joan Didion? I guess not.

My brother let me borrow his copy of Slouching Toward Bethlehem and I carried it around with me. My favorites were “On Keeping a Notebook” and “Goodbye to All That.” I’d never read that essay, and my brother was rusty on it, so one morning, I began reading it out loud. When I got to this part:

When I first saw New York, I was twenty, and it was summertime…

 I stopped and looked up at my brother who stopped what he was doing. “Wow, really?” he said. It was the same for me situation for me.

Since Williamsburg was the first place I lived without my parents, (Disneyland, as Angelica called it, making fun of me sometimes,) I was spoiled. The notion that every place I would ever move wouldn’t be sunny and compressed with bagels and strangers around each corner was not even a concept to me. Everywhere would be Disneyland.

Even though I am writing about New York, to say I was lonely would be a lie. I was tons of things in New York, but I never remember being unbearably lonely. One of my first jobs was at a costume jewelry shop on 66th Street and to get there, I had walk to through the underground transfer from the L train at 6th avenue to the 1 train. I always felt like we were a team. Here we go, I’d think to myself, while we all rushed, some of us even running, tripping over ourselves. Here we go, Team New York.

We were all in this beautiful shithole together.

Walking with my friend Lauren once, I said, “Watch out for that piss, don’t step in it,” and in her black Doc Martens, she stomped on it. It was dried to the pavement and everything—it’s not like it was a puddle, but still. We laughed and she said, “That’s my new thing. I step in piss.”

I wasn’t lonely. I was utterly overstimulated. New York moves you along. You move because you have to—always for reasons that sound ridiculous: exemption, condemnation, bed-bugs, a landlady with dementia, a roommate with bulimia. I moved from Williamsburg to Greenpoint. Greenpoint to Washington Heights. Then I landed in Inwood. Since I was so far out of Brooklyn, Angelica and I began to lose touch.

“The girl that never wanted to leave North 6th Street lives in Washington Heights!” Angelica said, choking on her own laugher, after I hadn’t seen her in some months. She couldn’t get over it. I’d once had declared that I never wanted to move—that I would live in my railroad apartment with no bedroom doors and two roommates in Williamsburg, forever. Imagine that.

I moved the same things over and over: My three-pound purple weights and my eight-pound lime green ones. My sunflower mirror. My polka-dot sheets. My father once came to help me during one of my moves and when we tied the mattress to the top of the car, he said, “You really should have taken the sheets off first!” While carrying futons up the narrow stairs in all of my different apartments he would lose his patience with my shitty sense of direction and say, “It’s like playing Tetris! Move it to the right!” When my panting became heavy he’d yell, “It builds character, come on!”

A lover from France who I’d known on North 6th Street came to visit with his dad when I lived in “The Heights.” He woke up one morning, looked around and sighed. In his accent, he said: “Still all the same shit.”

I wasn’t from Texas or California or Mississippi. I was from Spencertown, New York, a rural town of two-hundred people, only two hours away. I always knew I could go home. But in those first three years, I didn’t go home much, mostly just for the holidays. Looking back, maybe I should have. Now I always say that if I live in New York City again, I will remember to go upstate more. I grew up with woods and a stream behind my house. I grew up in a house where you could go outside naked and no one would see you. I grew up in a house where you could listen to music however loud you wished. A house where, as a child, I played “beauty parlor” in the woods, using mint leaves as perfume and berries as lipstick. If I ever missed nature in the city, I never thought about it. Once, Angelica came upstate with me and asked me why all the guys looked like bulldogs.

Here’s the thing I did think about constantly: Deep down, I was terrified that I would come to hate New York. I never wanted to be like any of the buzz kill people I met who hated New York. They’d been there too long. I sort of looked at Didion’s essay “Goodbye to All That” as a “how-to” essay, an informative essay. Like New York City for Dummies, or something. Didion more or less advises to leave New York before turning twenty-eight. She explains that things got very bad when she was twenty-eight. “It is quite possible to stay too long at the fair,” she says. I got that. It made sense to me. I decided that I wouldn’t be Joan Didion. I wouldn’t be Angelica. I wouldn’t be the guys at the Strand that didn’t know how to smile. No way. I was going to get out alive and go experience more Disneylands and more fairs. I decided I would move on April 30, a month after my twenty-third birthday.

Two nights before I left New York, I wore an Indian headdress and a bright fuchsia dress with a deep V-neck. Both the dress and headdress were borrowed. I sat at a table at Lucy’s Bar on Avenue A with my best friend Lauren, also wearing a headdress. We were drinking well whiskey and club soda. We were on our way to a sexual adventure—we had agreed to go have a five-some with the guy I was seeing, his best friend, and his younger brother.

We’d just snorted a bag of cocaine at the woman who lent me the dress’s house. She was a forty-year old ex-dominatrix, a British cokehead. She lived on 7th Street above the restaurant Casimir. We went over there to get cocaine and tips and confidence on how to have an orgy.

That night, I thought that I might explode. Just combust from excitement. I was aroused. Though, it could have been the cocaine talking. I thought that life couldn’t get any more colorful. I remember thinking: Does life get any better? Was this really the life I’d created for myself? Would I ever feel so much again? Was this good for me? Was I healthy? I went up to the bar and ordered two more glasses of whiskey for Lauren and me. We received some sidelong glances because we looked like freaks, but mostly, of course we were ignored.

I was too nervous to go to the five-some yet, so we kept drinking until we are ready. “Hurry,” my lover texted me. And then, “Get away from the coke.”

Lauren and I laughed hysterically and then I said wouldn’t it be funny to ring his bell, and then run, and she said we probably shouldn’t do that. When I confided in Lauren that I thought this whole situation was ludicrous—the headdresses, the coke, the sex, she told me that she thought maybe I was acting out because I knew I was leaving. I was milking New York, hard. That was for sure.

Susan Minot says, “Unless you were high up in a building or happened to glimpse it at the end of one of the big avenues going east-west, all you knew of the sunset was a darkening in the air. No wonder people in New York were so unbalanced. They were totally untouched by the rhythms of nature. You were only aware of nature when something extreme happened, like a snowstorm or heat wave.”

Totally unbalanced, is, when I look back on that night, precisely how I felt.

I loved every minute of it.

The night of the five-some was a total success. The next night my boss threw me a going-away-party at a bar in the West Village. Instead of mingling and talking to the people that came out to wish me off, I was going to the West Coast—I was so sore from sex and life, that I didn’t move from a booth for the whole night. When it was time to leave the bar I was overtired and I wept in the bathroom, for some unknown reason. Then I stood by the bar, in heels, waiting for my friends, and even though I was standing still, I completely wiped out and ate shit. It was like my body was broken. When we got back home, my friend ran me a hot shower.

The next morning, I packed my shit up for the fifth time. My friend Ashlee picked me up on Seaman Avenue. I didn’t cry. We listened to “Run, Baby, Run” by Sheryl Crow driving North on the Thruway and stopped at McDonald’s for milkshakes. I thought about the day three years earlier, when my mother drove me in the opposite direction, and how I was asleep on Vicodin, and I woke up just in time to see “Brooklyn: Like No Other Place In The World.” I should have believed that sign. I should have taken it more seriously.


 I moved to Washington state for a year because “I liked the place; I liked the idea of the place,” but I never came to like the reality of the place. No one really liked me either and there was never enough sun or food. When people ask me about it now, I’ve taken to saying, “I lived in Seattle for a year and then went running back to Brooklyn.” I over emphasize the word “running,” as if I actually ran. In Seattle, if you order a bagel, they give you the cream cheese on the side, in one of those Philadelphia packages, the way they do in school cafeterias. I was pissed.

I moved back to Brooklyn and though it wasn’t Williamsburg and I wasn’t twenty anymore, it still had the air of Disneyland. I was twenty-three and living in Bushwick. Wasn’t everyone?

Again, all I had to do in New York was show up. There was a mattress and a job at a café waiting for me. Some cities agree with you more than others. I got the Henry Miller sentence in my head in which he says, “I have no money. I have no resources. I am the happiest man alive.” Besides the resources part, that was my life exactly.

My first night back in Brooklyn, it was karaoke night at a bar called Tandem, and I wore all black and drank whiskey sang “Dreams” by Stevie Nicks. My friends and I stayed up in the living room into the wee hours of the morning, and my roommate mumbled, “Tomorrow we gotta get you a bagel.” I wrote in my journal: Brooklyn flatters me. New York flatters me. If I am five foot three then I am six foot seven. If I am 139 pounds I am 100.

On my second day back in Brooklyn, my friend Skye tied a blue ribbon around my wrist that read: I wish I could love and be loved in big cities. She told me when the ribbon falls off then the wish comes true. On my second day back in Brooklyn, I hula-hooped on a bed. I smoked a skinny blunt on a fire escape. At seven the next morning when the sun was coming up I walked toward my apartment on Suydam Street with Henry Miller’s Crazy Cock in my hand. The streets were wet and smelly and I saw three fat rats that I thought were beautiful. I got a coffee and a banana and sat on the curb and ate.

On my third day, I was on my way to Clinton-Hill for my new waitressing job. I walked down the stairs at the Jefferson Street stop in Bushwick, and sat down in a chair on the subway platform, eating a bagel and listening to my iPod. That’s when Angelica came down. We smiled and embraced. She told me she was married now. She was clean. She was a nanny. She was making crafts on a YouTube channel.

I went to the Strand to pee later that day, and I ran into another old friend outside. “Do you live here again, now?” He asked me, and I had to close my eyes and think about it for a minute and all of the previous fridges and beds I’d had in the past three years flashed before my eyes and then I opened my eyes and said, “Yes.” Relieved.

“Yes, I live here again, now.”

My mother called and she asked me about the weather.

“Honestly, mom? It could be hailing dog shit there and I would still say the weather was gorgeous,” I said.

“Do you have to be so vulgar?” she asked me.

You can’t help who you love.

I didn’t last three years this time. Three months later, I left New York again. I can’t sustain myself there—financially, mentally, physically. It makes me feel like a total pussy to admit that.

A few months later, a friend emailed me, congratulating me for leaving New York early. This is what he said:

 A buddy of mine who was a writer (sadly, he’s passed on) once lived in an apartment in the West Village that, he discovered, had years before been the home of William Styron. Being a big Styron fan, he eventually got around to writing Styron to tell him this, just as he was about to move South. Styron wrote back; the line that stuck with me from that letter was, “I think it is good that you are moving out of New York, if you want to write. New York is a great city but it is not a serious place to live [or words to that effect].”


Back when I was still “the girl that never wanted to leave North 6th Street,” Angelica burst through the door of my workplace in the West Village, a few days before my twenty-first birthday holding a large potted plant, to surprise me. At some point I’d been on this plant-kick, inspired by all of the greenery that decorated her apartment, and I’d mentioned how badly I’d wanted a plant. Angelica waited for me to close up the shop and then we started walking towards the L train on 14th Street. Angelica decided we should go to McDonald’s and get McChicken sandwiches and do some cocaine in the bathroom. We went in and I ordered while she used the bathroom. When she came out, she handed me the key, and said, “I’m going to get cigarettes down the street. Meet me at the bodega.” I went into the filthy bathroom, did a key bump of coke, and left. As I was leaving, a homeless woman, who had been denied the key by the McDonald’s staff, slithered by me.

I walked to the bodega and Angelica was standing outside, rolling herself a cigarette. She handed me one and we walked toward the subway to go to Brooklyn. It was warm outside so we thought, what the hell, we’ll walk to Union Square or even 1st Avenue, and take the train from there. Then Angelica stopped dead in her tracks.

“Where’s the plant!”

“Oh… FUCK!”

“You left it in the bathroom!”

We turned around back toward the McDonald’s.

The bathroom was locked. The homeless woman was gone. We asked for the key once again. The plant was gone. We ran all over 6th Avenue and 7th Avenue looking for the plant, until the sun went down and we gave up. I felt terrible and irresponsible and like a tremendous weight was lifted off of my shoulders. I hadn’t really wanted the plant. I was just trying on what it would be like to be the kind of person that would want a plant. I wouldn’t have known how to take care of the plant. Of course, as Emily Gould says, when her plant dies in And the Heart Says Whatever: “I suppose I could have Googled care instructions, back when it mattered, but then, I could have done a lot of things differently.”


For the time I lived in Seattle, I was a nanny, and I drove a borrowed mini-van. In the van was the album Tapestry by Carole King. I loved the song “Where You Lead” and while I drove the kids around like a soccer mom, I silently mourned New York.

The reason I listened to that song on repeat was because I liked the lyric:

“I always wanted a real home, with flowers on the window sill. But if you want to live in New York City, honey you know I will.”

This implies that you can’t have both—that if you live in New York City, you can’t also have flowers on your window sill.

I think you can have both. Can you have both? I want to have both.

New York and the flowers.

Chloe Caldwell is the author of the essay collection I’ll Tell You in Person (Coffee House/Emily Books, 2016), and the novella, WOMEN (Short Flight/Long Drive, 2014 and Harper Collins UK, 2017). Chloe’s work has appeared in Buzzfeed, Lenny Letter, New York Magazine, Longreads, Vice,, The Rumpus, Hobart, Nylon, The Sun, Men’s Health, The Nervous Breakdown, and half a dozen anthologies. She teaches creative nonfiction writing in New York City and online, and lives in Hudson. More from this author →