I’m Trapped in Downtown Manhattan

CultureAs a teen on the Upper West Side, the writer Annie Hamilton dreamed of becoming a downtown girl. But the wild life she eventually found below 14th Street proved to be less inspiring than her rowdy youth uptown.By Annie HamiltonDecember 16, 2024Michael Houtz; GoogleSave this storySaveSave this storySave“1234” by Feist was bumping at the 72nd Street Urban Outfitters while the cops handcuffed me and took me to jail. It was 2007; I was 15 years old.My plan had failed. I was going to buy four pairs of socks to secure a receipt and perform an imaginary “business call” as I passed through the metal detectors while exiting the store (in case the beeper went off). I’d wave off the security guard with my phone held up to my ear and tell him, “Please, sir, excuse me—I’m on Business.” I bought the socks, held the receipt, and made the fake call. But when the security guard yelled out and started to pull me back into the store, I wasn’t brave enough to make a run for it.I was taken downstairs. Several employees came down to watch. One took out his flip phone and snapped a few pics, or at least I was paranoid enough from a decent amount of morning cocaine to think so. Six cops soon arrived. A few began talking to the manager, but one of them just sat there, looking at me. I wasn’t sure what kind of look he was giving me. I remembered that “there’s no such thing as a free lunch.” The staring cop came over, his stare widening. He asked me if I had anything else on me that the law wouldn’t like. He said I could hand it to him and he’d throw it out. I gave him a fake ID from Delaware and the little baggy of morning cocaine as I wondered if he had kids. He left the office and threw my contraband away. I wondered if the cop should become my boyfriend. I wondered what would happen if I asked him out. That wouldn’t be a free lunch. That would be mutual gain. I asked the cop if he and his comrades could take me out a back exit. “I know I’m a criminal, here,” I remember saying. The words came to me surprisingly easily. I needed the back exit because girls from my high school were shopping upstairs. The cop nodded, but after briefly leaving the room again, he reported that there was no back exit. In future-boyfriend fashion, the cop decided he and his buddies would surround me and walk me out that way.That’s when “1,2,3,4” came on over the sound system. Even under arrest I remember thinking that it was catchy. The cops handcuffed and encircled me. We marched out to the beat of the song. I folded my body to get into the back of the cop car, just as I had seen them do in The Departed.The precinct was eight blocks away from my family’s apartment at the time. When the cop car pulled up, I tried to open the door myself. I thought it would be a good look, to be a willing prisoner. The cops didn’t think so. They made sure I stayed put. I was enrolled at a $50,000-a-year private school at the time, but I wasn’t yet totally aware of my immense privilege. I knew the nice cop was a weird thing to happen to someone, but the whole thing was pretty weird. My father had just filed for bankruptcy. I was feeling dramatic about it. I was feeling sorry for myself. It’s dangerous to feel sorry for yourself, and pointless, so I coped by making messes that were all my fault all on my own.I sat in the holding cell and weeped. When it was time to take my mugshot, the cops told me to stop crying. Holding back my tears, I pursed my lips. I remember thinking I looked pretty distressed and also pretty pretty in the picture I saw projected on the screen.I went to court and came out with a community-service sentence. I don’t remember much from doing the service, beyond Windexing a framed photo of Mayor Bloomberg.I grew up on the Upper West Side. It wasn’t a typical upbringing, but I’m not an orphan yet.As an adolescent, I was sure that growing up uptown would inhibit me from becoming the person I wanted to become. I longed to live downtown. I couldn’t think of anything else that could successfully turn me into a cool person. I thought I had smarts, but I knew I was missing cool. Around the time I first started shaving, when fashion magazines were my bibles, I read that Chloë Sevigny rarely even traveled above 23rd street (don’t quote me on that). Growing up on the UWS’s rat-less streets felt like solid proof that I was destined to be uninteresting. What I wanted to become was some sorta variation on a Factory Girl.I left New York at 18 for California. I wanted to get as far away from my family, from the Upper West Side, as physically possible. I didn’t think I’d ever return.Let’s just say Los Angeles isn’t for me, but I stayed there for 10 years, because I didn’t want to return to New York empty-handed. Four years ago, I ran out of options. The only roads I hadn’t been down were clear dead ends. I had to get out of there. I had to get out so bad that I moved at the height of quarantine—sold all of my stuff, aside from my books—and got my ass back here. I

Dec 17, 2024 - 12:18
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I’m Trapped in Downtown Manhattan
As a teen on the Upper West Side, the writer Annie Hamilton dreamed of becoming a downtown girl. But the wild life she eventually found below 14th Street proved to be less inspiring than her rowdy youth uptown.
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Michael Houtz; Google

“1234” by Feist was bumping at the 72nd Street Urban Outfitters while the cops handcuffed me and took me to jail. It was 2007; I was 15 years old.

My plan had failed. I was going to buy four pairs of socks to secure a receipt and perform an imaginary “business call” as I passed through the metal detectors while exiting the store (in case the beeper went off). I’d wave off the security guard with my phone held up to my ear and tell him, “Please, sir, excuse me—I’m on Business.” I bought the socks, held the receipt, and made the fake call. But when the security guard yelled out and started to pull me back into the store, I wasn’t brave enough to make a run for it.

I was taken downstairs. Several employees came down to watch. One took out his flip phone and snapped a few pics, or at least I was paranoid enough from a decent amount of morning cocaine to think so. Six cops soon arrived. A few began talking to the manager, but one of them just sat there, looking at me. I wasn’t sure what kind of look he was giving me. I remembered that “there’s no such thing as a free lunch.” The staring cop came over, his stare widening. He asked me if I had anything else on me that the law wouldn’t like. He said I could hand it to him and he’d throw it out. I gave him a fake ID from Delaware and the little baggy of morning cocaine as I wondered if he had kids. He left the office and threw my contraband away. I wondered if the cop should become my boyfriend. I wondered what would happen if I asked him out. That wouldn’t be a free lunch. That would be mutual gain. I asked the cop if he and his comrades could take me out a back exit. “I know I’m a criminal, here,” I remember saying. The words came to me surprisingly easily. I needed the back exit because girls from my high school were shopping upstairs. The cop nodded, but after briefly leaving the room again, he reported that there was no back exit. In future-boyfriend fashion, the cop decided he and his buddies would surround me and walk me out that way.

That’s when “1,2,3,4” came on over the sound system. Even under arrest I remember thinking that it was catchy. The cops handcuffed and encircled me. We marched out to the beat of the song. I folded my body to get into the back of the cop car, just as I had seen them do in The Departed.

The precinct was eight blocks away from my family’s apartment at the time. When the cop car pulled up, I tried to open the door myself. I thought it would be a good look, to be a willing prisoner. The cops didn’t think so. They made sure I stayed put. I was enrolled at a $50,000-a-year private school at the time, but I wasn’t yet totally aware of my immense privilege. I knew the nice cop was a weird thing to happen to someone, but the whole thing was pretty weird. My father had just filed for bankruptcy. I was feeling dramatic about it. I was feeling sorry for myself. It’s dangerous to feel sorry for yourself, and pointless, so I coped by making messes that were all my fault all on my own.

I sat in the holding cell and weeped. When it was time to take my mugshot, the cops told me to stop crying. Holding back my tears, I pursed my lips. I remember thinking I looked pretty distressed and also pretty pretty in the picture I saw projected on the screen.

I went to court and came out with a community-service sentence. I don’t remember much from doing the service, beyond Windexing a framed photo of Mayor Bloomberg.


I grew up on the Upper West Side. It wasn’t a typical upbringing, but I’m not an orphan yet.

As an adolescent, I was sure that growing up uptown would inhibit me from becoming the person I wanted to become. I longed to live downtown. I couldn’t think of anything else that could successfully turn me into a cool person. I thought I had smarts, but I knew I was missing cool. Around the time I first started shaving, when fashion magazines were my bibles, I read that Chloë Sevigny rarely even traveled above 23rd street (don’t quote me on that). Growing up on the UWS’s rat-less streets felt like solid proof that I was destined to be uninteresting. What I wanted to become was some sorta variation on a Factory Girl.

I left New York at 18 for California. I wanted to get as far away from my family, from the Upper West Side, as physically possible. I didn’t think I’d ever return.

Let’s just say Los Angeles isn’t for me, but I stayed there for 10 years, because I didn’t want to return to New York empty-handed. Four years ago, I ran out of options. The only roads I hadn’t been down were clear dead ends. I had to get out of there. I had to get out so bad that I moved at the height of quarantine—sold all of my stuff, aside from my books—and got my ass back here. I found myself a sublet downtown.

In the beginning I liked living below 14th street. At first I thought even the garbage had more texture to it. I was entranced by the length of the Bowery, by Tribeca’s cobblestone pavement. How nice it was to walk out of the apartment and immediately be attracted to passersby. I got an education in partying. I tried to make whoever was in front of me laugh. I learned that it’s important (to me) to try to be funny. I saw magic shows and dance shows and went to concerts and to the theater. I spent all of my money on expensive dinners. I remembered that I liked to write, and I became a writer.

After a stint in Chinatown, I sublet a tiny bedroom (just enough room for a twin-size bed) in Little Italy. I got sick of sleeping alone every night, so I started staying at a friend’s place on the Lower East Side. When said friend had enough, I briefly moved to Brooklyn, the top floor of a four-story walk up in Fort Greene. And then, a year and a half ago, I moved into my own place (no goddamn motherfucking roommates) in the East Village.

Living in the East Village is a problem for me. I don’t care for the scenery. Sorry; I don’t. I like walking past La MaMa and McSorley’s and going to The Scratcher, but that’s about it. It’s me and a bunch of yuppies out there. (Yuppies don’t think I’m attractive, and I only think they’re attractive sometimes.) I had pictured the EV being me and a bunch of neighborhood old-timers, but the old-timers that are there seem to mistake me for a yuppie. Maybe I am a yuppie! (I’m probably a mix between a yuppie and an old-timer; I’m not saying that it’s a good mix, but that’s the mix.) But perhaps the biggest problem with the East Village is the whole walk-out-of-my-apartment-and-run-into-someone-I’ve-slept-with thing. I used to like running into ex-flings when I lived in Dimes Square. But I don’t want that anymore. Allow me to walk around with unbrushed teeth.


It was when I was living in Dimes Square—the area between Chinatown and the East Village, where much of what we think of as “downtown culture” flowered (or festered) in recent years—I discovered my only consistent routine for writing: taking a walk. The apartment that I shared had no windows in the living room. And while it did have a window, my bedroom was too small to fit a desk. Natural light helps me think, and walking hands me ideas. I’d walk as far and as long as I could in those first two years back in New York, listening to music, and I always wound up on the Upper West Side. No matter how much I pushed for inspiration downtown, I was getting my best ideas up there. I’d reach The Dakota, and something would click. I was extremely displeased to learn that remembering my childhood would turn out to be a key part of my creative process.

The first time I discovered the profundity—the exorcism!—of writing, was on 86th and Broadway, on the night I lost my virginity. I lost it on the Upper East Side, which is what the Upper East Side is good for. I had been kicked out of this high school QB’s apartment at 4 a.m., so that his parents wouldn’t find me there in the morning. (Leave him alone; he didn’t know I was a virgin. I lied and said I was on my period.)

My mother always chained the door of our apartment at 1 a.m. to discourage me from staying out too late. I had a 12:30 a.m. curfew and a 30-minute grace period. I couldn’t go home. I wouldn’t have been able to get into the apartment.

I wandered from 93rd and Lexington—through Central Park; I was young—and found myself in a Duane Reade on 87th and Broadway. I bought Plan B with a fake ID (a new one) and a notebook to entertain myself. I knew I didn’t need the Plan B, but I bought it anyway; my flip phone had run out of battery, so I couldn’t ask for a friend’s opinion on the matter. I walked to French Roast, one of the UWS’ only 24-hour joints, sat and ordered an onion soup, and between 5 a.m. and 8 a.m. began to document the night’s experience. (Returning to my mother’s at 8:00 meant it was plausible I could’ve slept over at my friend Celine’s.) I wrote about wondering if the man sitting at the table next to me could smell the blood in my underwear. I wrote about how I wasn’t in love, or in pain, or inhabited by any feelings that I could identify. I wrote about how I knew the guy would never be interested in actually dating me. I thought about my copy of Love is a Dog From Hell and wrote some insults. Later I published the “piece” in my high-school lit mag (the gall).

My favorite memories of growing up are of nights spent getting dead-drunk on Columbus Avenue and of days spent walking down Central Park West listening to Tom Waits’ first album (or the Vampire Weekend Pandora Station). Life was filled with infinite possibility. I knew New York City would wait for me to grow up.

I smoked pot on 110th and Amsterdam to pass the time, and used the perfume samples from newsstand magazines to hide the stink on my way home. The first time I “saw” Annie Hall was on 87th Street and West End Ave. I was in bed, trying to fall asleep but heard the sound from my mother’s bedroom. That apartment was just two blocks from where J. Robert Oppenheimer grew up. I liked smoking pot outside of his place too. (Me and Opp share the same high school alma mater—the truest of flexes, I know.) My father gave me my first “sex talk”—in which he told me that I’d never be with a man who wouldn’t cheat on me—in the Murders in the Building building. That’s on 86th Street. We lived there for a couple of years. And, hey, it wasn’t the falsest advice. I’ve received falser.


I had a good run downtown. I met some of my closest friends while living in Dimes (RIP). Run-ins back then set me aflame, set me electric. I felt special downtown, like I was being discovered. I liked being the first one at the party and the last one to go home. I liked following the night wherever it would take me, even if it took me to Long Island City. I liked ending up at Russian Samovar and walking all the way home shit-faced. Hell, I liked walking home shit-faced from ANYWHERE. I especially liked walking home shit-faced from karaoke; eventually, I learned it was time to stop walking home shit-faced from karaoke. Eventually, I learned it was time to stop walking home shit-faced at all. I had a real good time being out of control, though you don’t get a lot of lasting memories that way.

I worked at a restaurant on West 4th and had a great time sleeping with customers. I had an even better time sleeping with one of the bartenders who had a girlfriend. I liked pretending I was “bad.” Maybe I even became “bad.” Being bad felt like being on the cusp of something. I wasn’t exactly on the cusp of something, but I stopped caring what people thought of me so much. I tested out being a bitch. Turns out, I like being a bitch. Being nice makes me happier at the end of the day, but being a bitch is necessary sometimes. Living downtown taught me that a lot of people don’t like me, but that life is too short to think about it.

I no longer think of myself as a downtown girl. I’m not cool. I’m not freaky in a fun way. I’m not a good-time girl. I’m neurotic. I’m intense. I’m…whatever I am. I’m a half Jewish girl from the Upper West Side. Plus, it is not my ideal lifestyle for my friends to know where to find me. I don’t let anyone have me on Find My Friends, but LIFE is a damned Find My Friends below 14th street. So you’ll see me down there sulking. You’ll see me on the phone, holding fake Business calls. You’ll see me holding hands with someone I’ve known for two days. I’ll be walking home from karaoke, not particularly shit-faced.

To hell with it! Central Park is the best place on earth! Gray’s Papaya can nurse me through any kinda breakup! I’d like my ashes scattered in Riverside Park! Place my urn in the New York Historical Society or better yet in the Lincoln Center Performing Arts Library. Install my bones into the walls of Juilliard! They’d make a nice shelf—a shelf for other people’s awards.

The neighborhood I thought I wouldn’t ever be proud of turns out to be the neighborhood I most want to call my home. But as sick as I am of living down here, I’m unable to make my exit. I don’t have the cash flow to move uptown, or to move anywhere—yet. Kind of, dare I say, downtown of me. Or at least, the downtown I grew up reading about.

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