The Oprah doppleganger wore a dramatic sweater-cloak type thing draped over her shoulders. It fastened at the throat with a button that was the size and shape of an iridescent drink coaster. The garment’s material was blindingly white and featured intricate patterns in the stitching. The patterns reminded me of a well-groomed ski resort, and I said as much. Both women laughed then congratulated me on my observation. I took their drink order and promised to return in two shakes.

Reynaldo tailed me to the bar and asked me how it was going. I felt like a boxer receiving a between-rounds pep talk. “I have them right where I want them,” I said. He said that he’d waited on these two mummies before and that they had a reputation for being fussy. “They once sent back a piece of mahi mahi four times,” he said. He told me to stay on top of them, to “overservice” them—I nodded as if I understood, but it was a term I wasn’t familiar with—and that if I got into “the weeds”—another term I wasn’t familiar with—he’d be there for me.

Jeeta the bartender placed the two drinks for the ladies on the bar. A grumpy little bottle of Perrier stood in the shadow of the tallest wineglass I’d ever seen. I wondered if someone was having a laugh, using a huge, joke wineglass as a way to pick on the new guy. Jeeta, who never smiled and who was likely born with a furrowed brow, assured me that in The Club’s decade-long history the wineglasses had always been regulation-size.

I placed the Perrier bottle on one section of my circular tray and the joke wine glass on the opposite side, trying to counterbalance the weight of one drink against the other. When I picked up the tray with the drinks on it, everything began to wobble. I immediately set the tray back down, then picked it up a second time. Using both hands to carry it, I began to shuffle my way across the restaurant towards my first table, and towards my great undoing.

Carrying trays with drinks on them was something I’d seen waiters do in restaurants for years, never having any idea that tray-carrying was a bona fide skill. I’d seen waiters carry trays crammed with drinks and plates, with the entire thing balanced on the very tips of their fingers. How they pulled off such a feat was a complete mystery to me. Even my smallest movements, the slightest tilt, sent a seismic jolt through the tray causing the blood-red cabernet to roil like Homer’s wine-dark sea inside the glass, first careening from one side then back to the other. I felt like I was trying to balance an overfilled fishbowl on top of a chopstick. I marveled at how utterly impractical this vessel was, how poorly designed the wineglass was for its intended purpose. I understood now why people were always hurling them into fireplaces in movies.

My journey across the restaurant—and it truly was a journey, involving multiple close calls followed by near-miraculous recoveries—seemed to span several hours, though it probably only lasted a matter of minutes. By the time I reached the Oprah Doppleganger and her companion, I was sweating openly. Sweat streamed down the sides of my face and gathered at my chin. “Well, hello again, ladies,” I said, winking and hoping they wouldn’t notice the sweat, or the panicked expression on my face. “Did you miss me?” I asked. As soon as I lifted the Perrier bottle from one side of the tray, the tallest glass of wine in the world went over.

The roiling cabernet, nearly every drop of it, splashed down the front of the Oprah doppleganger’s pristine sweater-cloak. She stood up so quickly that her chair tipped over.  The restaurant went quiet. Everyone, still chewing like cows and holding their utensils, turned in their seats to see what the commotion was. The woman looked down at her ruined sweater-cloak, her eyes welling up with pain and anger, her chest rising and falling. Her mouth hung open. She looked like she’d butchered a gazelle with a chainsaw and she knew it.

“How dare you!” she said, pointing at me. She said it a few more times. “How dare you! How dare you!” Each time she said those words—”How dare you!”—felt like a hammer-blow to the back of my neck.

My farce at the East River Club was over. Whatever wool-pulling I presumed I was getting away with was obviously finished now. No seasoned waiter would ever make such a gaffe. I could hear Mr. Galanti’s dress shoes striding with great purpose across the restaurant’s parquet flooring. He put a hand on my shoulder, leaned towards me and said under his breath, “Get the fuck off the floor now.”

I retreated to the employee locker room, which felt like the safest place in the building to me. I sat on one of the benches in a stunned state and tried to figure out what I was supposed to do next. It had been obvious to me from the start that I didn’t belong here, that I didn’t have the sand for city life. I wasn’t even sure why I thought coming here was such a hot idea in the first place. I’d launched myself into the unknown, mostly because I had no grand plan, no better idea for what to do with my life.

I suppose that I also wanted to see if I could do it, if I could pull it off. There was a morbid curiosity underlying this enterprise, not unlike watching a daredevil attempt to jump over a fire pit. For three months I’d hurled myself into the gears of the city, and what did I have to show for it? I had an apartment the size of a prison cell that I couldn’t afford. I had no car, no real friends, and no love. I had a laundry schedule that involved me getting up in the middle of the night. The closest thing I had to friends were a pair of street-roaming cross-dressers wearing Tina Turner wigs. It was time for me to go. Time to concede, to accept my fate as a small towner, and return to where I belonged: my small town. I kept hearing that woman’s voice like a mantra in my head: how dare you, how dare you. She was exactly right—how dare I? Who did I think I was, trying to fool these street-smart city people? I changed my clothes and stuffed my uniform into a plastic shopping bag.

After the dinner shift, I found Mr. Galanti in his office doing paperwork and eating a sandwich. He told me to close the door and then motioned for me to take a seat. The fluorescent lights in his office were painfully bright. He looked at me across his desk. “Well?” he said.

Like the church-going Catholic boy I once was, I confessed everything. I apologized for lying to him, for attempting to pass myself off as an experienced waiter when I clearly was not. I told him that I appreciated the opportunity he’d given me, one that I didn’t deserve. The unburdening was making me feel better. This was a moment of personal reckoning, a moment when lies and posturing—two things which I was certain city life would require of me—had no value. This was the first time in months that I felt like I could relax into being my old, flawed self again.

Mr. Galanti wiped his mouth. He planted his elbows on his desk. I once again noticed the framed photo of him and his collie, both wearing bright orange life jackets, both looking pure and happy, the sun on their faces. It was a silly photo to have on your desk, but it was an honest photo. Mr. Galanti clearly loved that collie enough to put a life jacket around its neck, then have his photo taken with it. “I’ve been in this business for 20 years,” he said. “I know a green waiter when I see one. I knew you were green as they come. Despite your shit credentials, I made the decision to put you out there anyway. Normally, I would never do such a thing. But you seemed like a decent kid. And, right now, I need decent kids more than I need waiters with experience. So this is what I want you to do. I want you to hang onto your uniform for now. Show up tomorrow for your lunch shift. Practice carrying things on trays. And, if you’re still spilling wine on my customers a month from now, then we can talk about you leaving.”

The Oprah doppleganger, he said, had demanded that I be fired. “I talked her down,” he said. “I comped her check. She’ll bill us for the sweater that you ruined. In my opinion, you did her a favor. That thing was awful. Also, Nancy gave her some passes for a show, so it’s all taken care of. Oh, and this belongs to you.” He produced a garbage bag from underneath his desk and tossed it to me. Inside was the woman’s cabernet-soaked garment. “She left it here,” Mr. Galanti said. “She kept saying the words, ‘You bought it; it’s yours now.'”

I told him that he would not be disappointed, even though I would eventually disappoint him, in countless ways. Once our meeting was over, I headed for the series of secret hallways that led to the discreet employee exit. I burst through the doors, feeling the damp Chicago River air on my face—the first real air I’d felt in hours. I’d square-danced with doom yet again, and somehow I’d survived. Somehow I was still standing. Two women passed in the shadows and I froze. I was paranoid that one of them was the woman I’d embarrassed, that she was out here lying in wait for me by the employee exit, prepared to hurt me the way that I’d hurt her.

When I realized it was simply two random city dwellers, I ran down the street at top speed, running until my thighs burned, screaming at the top of my lungs. I was letting Chicago know that I wasn’t done, not yet, not by a longshot. I was still here to do damage, to kick ass, to take names. A few blocks from The Club, I slam-dunked the trash bag with the sweater inside into one of the corner garbage cans, the same way Michael Jordan was forever slam-dunking basketballs on every TV screen in Chicago. I raised my arms in victory, ran in a circle a couple times.

I started to walk away, but then went back to the trash. I pulled the sweater out, digging into the garbage bag. I yanked the iridescent coaster-size button off of it, claiming it as a trophy. I stuffed the button into my back pocket, then headed for my busstop.