This is my sixth visit to the small claims court building and I am beginning to feel like a regular. There are the friendly cops downstairs who scan my purse for weapons and ask if I know where I’m going, always more cheerful than I ever am–because yes, by this point I know all too well I am headed. Once I get upstairs, I can tune out while the clerk reads the script about the rules of the courtroom, as I’ve nearly got it memorized. And after much trial and error, I now know the quickest route to my new favorite Chinese restaurant on East Broadway, which serves delicate little dumplings that are the perfect comfort food after several hours on a hard courtroom bench.

Small claims is the ugly stepchild of the Manhattan court system. The main room, besides the lack of windows, is shabby and overcrowded. It smells like stale body odor. The fluorescent lighting makes even the healthiest people look like they are recovering from a nasty case of food poisoning. Since damages are limited to $5000, the demographic tends to lean toward the mid- to low-income and the paranoid. Almost no one dresses up–not even the judges, who by the end of the day cannot help but look like rumpled civil servants.

Small claims court has neither glamour nor grandeur of purpose. This is where people come to complain of a botched kitchen renovation or auto body damage from a routine fender-bender. But, if you look up from your book long enough to eavesdrop on the other cases, a narrative begins to emerge. Between the lines of trial testimony are stories of broken friendships and lives eked out on the margins–of life in a city that defies you to stay here in spite of all its everyday injustices.

One night I listened, rapt, as a woman tearfully told the judge one of those New York horror stories involving a shady roommate service, a surprise eviction, and an inconvenient cat. Occasionally, the drone of the air conditioning is punctuated by moments of excitement when, for example, a witness who cannot contain himself speaks out of turn and the judge has to reprimand him–just like it happens on television.

Sometimes it feels as if the city itself is on display in rawest form. Drama, banality, joy, pathos–it’s all there. Or perhaps I have just spent too much time here.

The first time I appeared in court, way back in March, I was fresh-faced and hopeful, like a passionate rookie defense attorney on my first big case. There was no way, I thought, that any honest judge could possibly side with my opponent, the venal management company that was trying to deprive me of my $1100 security deposit. File folder in hand, I wore a blazer and freshly pressed trousers, only to discover that the dress code was more along the lines of “No Shirt, No Shoes, No Service,” and that justice can be elusive in the face of bureaucracy. It can take several court appearances to actually see a judge, and even if you win it is up to you to retrieve your money. Now I am like that young attorney’s older, hard-drinking coworker, embittered and world-weary from years of disappointment. Cynicism is my best friend.

My lawsuit, which began as an intimidation tactic to get my deposit back, has devolved into a war of attrition, or, more accurately, a game of chicken. One of the last times I was here, the woman representing the management company, whom I had mistakenly dismissed as an amateur, outsmarted me. We had finally sat down for a trial when she announced to the judge that she had only just now realized that all along I should have been suing the landlord, which was technically, if not practically, a separate entity. The judge looked at me sympathetically, told me that this was a common stalling technique used to wear people down, and gave me another date in time to add a new party to the suit.

Later that evening, my mother–who, bless her, has faithfully come as my witness to each appearance–became emotional over dim sum: “These people,” she said, referring to the management company, despair creeping into her voice, “are capable of anything.” She shook her head at her dumplings. “Anything!” This is what small claims court does to you–it saps you of your innocence even as it fills you with righteous indignation.

This being New York, however, there are people who treat small claims court as an opportunity. On one of my visits to 111 Centre Street, I got asked out on a date by a man using that tired line, “Don’t I know you from somewhere?” I considered it for a moment, if only because it would make a great story–You may not believe this, I’d tell people, We actually met at small claims court–but the guy kind of creeped me out and I decided that no story is worth ending up with a potential stalker. I made up a lie, told him I couldn’t give him my number, and watched my back all the way to the subway.

As I wait for my name to be called on what I hope will be my last court date, I begin to long for Chicago, where I have lived for most of the last year and where I will soon return after spending the summer in New York. In Chicago you can find an apartment in an afternoon, no brokers or roommate services needed. Public transit workers smile at you when you pay your fare. Life there is, well, easier. And it even has a great, hulking skyline that from certain angles almost rivals the view from the Brooklyn promenade.

Chicagoans like to put on their most jaded smirk and tell you that the reason their city runs more efficiently is because of all the corruption. Restaurants may have to bribe someone at City Hall for a liquor license, but the streets are indeed cleaner. Going to the DMV is like visiting a warm, chatty aunt. And, though I’ve never been, I have a feeling you wouldn’t have to show up to Chicago small claims court more than three times to get a resolution.

Chicago is lighter on the nerves. But it is the thrill of frustration that makes me pine for New York–with all its maddening, addictive aggravation.

Sarah Miller-Davenport is a writer living in Chicago.

It is a beautiful boot, though—Marc Jacobs, in black pebble leather with pinstriped suede trim and a small heel—and for a second or two I wonder what it would feel like to go into credit card debt for the sake of fashion. I glance around at the well-heeled women in the shoe department and try to conjure up a feeling of righteousness to ward off the sense of shame that kicked in as soon as soon as I passed through the revolving door downstairs. Shame over being trespasser, a class tourist in a rich-person’s department store. Shame over caring what rich people thought of me. And shame at what my mother would think about the whole episode.

When I was growing up in New York City, my mother never took me into stores like Bergdorf’s. We went shopping for shoes and nice dresses to wear to synagogue on the Lower East Side. That was where Jews went for shoes and nice dresses, even as late as the 1980s and even though the shoe store was next door to an empty lot piled with bricks and dirty needles.

The rest of my clothes came from Conway or other discount stores in Herald Square, or Macy’s, if they were having a sale. My mother would go shopping on her lunch break and come home with bagloads of outfits for me to try on at home, returning what I didn’t want the next day. I would model them for her in the living room and agonize over the prospect of offending the manufacturers of the items I had rejected. I must have known, through the fog of child-logic, that my feelings of guilt were completely misplaced, that what I was really afraid of was hurting my mother. That is how I ended up with a pair of pleated acid-washed jeans in the style of A.C. Slater from “Saved by the Bell,” worn once and then stuffed into the back of my closet.

A common refrain in my family, at least one spoken by me and my father, was, “We’re not going to the poorhouse!” This was usually met with indignation by my mother, who would snap back, “You don’t understand how little we live on. You don’t pay the bills!” And both my dad and I would have to let it go since she was right—certainly about the bill-paying part.

Still, I was resentful, and felt downright deprived, when in the fifth grade she refused me a pair of metallic spandex leggings, which were deemed too expensive. As a consolation prize, I got some ribbed pseudo-leggings from Conway that were barely tight enough to fit into my slouch socks. (The socks were not quite right either.)

I should say here that we lived in a comfortable pre-war apartment on the Upper West Side of Manhattan. I grew up in relative privilege. We had a car, a dog, and went on the occasional family vacation. I went to private school, which was paid for by my grandmother. But money was always tight, and spending it was fraught with anxiety.

The department stores on the east side—Saks, Bendel’s, Bergdorf’s, even Bloomingdale’s—were off-limits. They were the bastions of the rich and insouciant, with snooty salespeople and spoiled customers, easier to scorn than to risk their rejection. My parents, liberal stalwarts in a time of Reagan-era excess, wore their fashion cluelessness like a badge of honor. They rooted for the downfall of junk bond king Michael Milken, and cheered when Barney’s was tarred by charges of racial discrimination.

I had expensive taste, my mother liked to tell me, and not without a hint of admonition. The daughter of a rabbi, her wardrobe as a teenager consisted of hand-me-downs from her father’s congregants. When owning a cashmere sweater was all the rage in 1950s Baltimore, she had to wait until some other girl got tired of hers. My mother didn’t have many stories about growing up, but this was one of them. Somehow, I sensed that the sweater trauma was somehow connected to the other iconic story of her childhood, in which my mother spent most daylight hours after school alone, in the public library.

My father had not known such want as a teenager. His disdain for fashionable clothes was less an embrace of frugality than it was a rejection of his WASP upbringing. One summer during high school his parents had sent him to a tailor for a custom-made suit to wear to all the Louisville debutante parties and he came back with a jacket and pants made of mattress ticking. He dismissed my material longings with the casualness of someone who had never coveted a cashmere sweater.

In the ninth grade, when I transferred to a fancy private school on the Upper East Side, my own fashion sense went a little haywire. Realizing there was no way I could keep up with my wealthier peers, I turned to buying all my clothes at the Salvation Army. I thought I had special skills when it came to spotting the best T-shirts—soft and worn, with some sort of ironic slogan or nonsensical text on the front— from among the rows of musty closet detritus. This, to my mother, was more economical and thus better than shopping retail, even though I went through most of high school wearing a hot-pink ski jacket as an overcoat.

That all changed once I had my own place in New York and a small, but independently earned sum of money in my bank account. Shopping in New York is like a drug: the more money you spend, the more you want to spend. And once you pass your limit of what is an appropriate price for, say, a perfect black cotton top or a really, really great pair of flip flops, it is hard to go back. Instead, I justify any extravagances with the argument that, for people like me, with no innate style, expensive clothes make us look better.

This doesn’t mean that I won’t immediately call my mother to confess when I spend too much money on a pair of shoes and then refuse to tell her how much they cost. When she asks me, with an innocence that verges on poignant, “Were they more than $75?,” I realize that if she knew just how much more she might think less of me.

This is a woman whose own mother, two generations out of the shtetl, washed and reused tin foil—and not because she was an environmentalist. I am pretty certain my mother, who has lived in New York for four decades, has never seen the inside of Bergdorf’s, the ultimate gatekeeper of the upper caste lifestyle. Bergdorf’s radiates posh. It has soft, flattering lighting, and etched mirrors in the escalator shafts. It lacks the crushing din of manic shoppers looking for the sale rack. Even the shopping bags—lavender with indigo text in deco font and a graphic of figures who look like they’re on their way to a Jay Gatsby party—are a paradigm of high-class understatement. And although many of the customers are teenagers and women in their twenties wearing oversized sunglasses and skinny jeans, the whiff of old money in Bergdorf’s is pungent.

Walking through the ground floor, past rows of jewels that cost as much as a car, I can’t help but feel that being here is a small act of betrayal. This is a place where it is acceptable, in fact encouraged, to spend $900 on a pair of boots. Not that I ever have spent $900 on a pair of boots. But I plan to someday. Then I will call my mom.