Jimmy’s Corner isn’t like other Times Square bars–those oversized Irish pubs made of dark, polished wood or the theater-crowd cocktail lounges with big windows, people inside looking like they’re drinking in a department store display case. Jimmy’s is a dim, narrow cave of a bar, a hunk of coal in a glittering craton. Late in the afternoon and into the evening, Jimmy’s is crowded with office workers and tradesmen who stand or sit at the bar and around the tables in back. Jimmy’s never gets very noisy, but there is a constant hum of conversation and the small size of the place seems to encourage strangers to talk to one another. Recently, after some talk became overheated, small signs that said, “Let’s not discuss politics here,” appeared behind the bar.

Once every couple of weeks, my friend Ben and I would stop into Jimmy’s after work for a few drinks. We were maybe four beers into a Thursday night in February when a woman–blonde, thin, pale and pretty–tapped me on the shoulder and said, “Excuse me, can I talk to you outside for a minute?”

I liked Jimmy’s because it was exactly the kind of place where a stranger might walk up to you and ask you to step outside–the kind of place where almost anything could happen. It has just one small window which is shaded from Times Square’s twitching lights by a broad awning. In the taxonomy of New York bars, Jimmy’s isn’t a relic, like McSorley’s or the Whitehorse, with their flawlessly aged wood and manicured sawdust on the floor. At Jimmy’s, survival, not preservation, is the first order of business. Show up early enough and you’ll see Jimmy behind the bar or at one of the tables in back, sipping from a shot glass. If you don’t see him, just look at the walls: he’s framed up ringside with Ali, with Liston, with scores of nameless fighters, fists raised, knees bent, ready. Show up late–anytime after six–and forget the table because the place will be full, and the bartender will just shake his head at you and point you back to the sidewalk.

You’d see things at Jimmy’s that you couldn’t fully explain. One night I watched Jimmy shuffle up and down the bar, stopping periodically to place two shots of liquor in front of random customers. Without a sound except the slap of Jimmy’s hand on the bar, they’d lift their glasses and down the shot together. Other nights the pretty young waitresses would disappear one by one into the back room for fifteen minutes at a time, and before they’d close the door behind them I’d catch a glimpse of Jimmy sitting on a metal folding chair, watching the girls walk in with what I imagined to be sweet anticipation. Those happenings were evidence of an unseen order, a veil of mystery that left you nothing to do but sit back and wait until something strange or sordid happened to you.

So, on that particular Thursday night in February, Ben and I had a table for two and watched Jimmy’s Corner get packed, watched the old guys pump the jukebox for soul numbers, watched this petite blonde walk right up to me and ask me to step outside, like a surly welterweight with too much whiskey in him. We sat there for a minute, Ben and I did, with the woman standing over us, traffic backing up behind her in the narrow aisle, her question, her rice paper voice, the noise of the whole bar swallowed by the sound of Nina Simone singing “I Put a Spell on You.” She held herself back; she was on her heels, arms crossed, shoulders caved in around her ribcage, the shape of uncertainty.

“Outside?” I said.

“Just for a minute.”

I got up and followed her past the jukebox, guys stacked three deep in the aisle now, sucking in guts to let us pass. Outside, a skinny black guy stood under the corner of the awning, smoking a cigarette and staring at the lights of the square as they broke like waves over skyscraper glass. He absently dipped his penny loafered toe in and out of the gutter. Someone asked which way to 44th Street and he said, “You’re on it.” The blond turned around and faced me, smiling an embarrassed smile. Her brown coat was unzipped, sweatshirt and jeans underneath. She looked like she had just run out to get a quart of milk. She stepped in close to me, put her mouth next to my cheek and said, “My husband and I are looking for a third to join us.”

I was looking across the street at one of the theater crowd restaurants. It was almost empty–curtain was an hour ago–and a band of black-shirted waiters idled in a corner by the window, three of them watching over a pair of diners on the far banquette, a fourth staring out the enormous window. This may account for why I said, “Join you for dinner?”

“No, not for dinner,” she said, still smiling but with a new boldness. I understood now, and she was delighting in the fact that I was the one on my heels. “We don’t do this very often.” She said.

“Where’s your husband? Is he here?” I asked.

“Yeah, he’s inside. I don’t want to point him out to you yet. We really don’t do this very often,” she said again, embarrassed, like she was talking about ballroom dancing or eating with chopsticks. It was my turn to talk, but I didn’t know what to say. I’m no prude–I don’t have a problem with casual sex with multiple anonymous partners, at least on principle, but the whole thing had a transactional feeling, like it could have been happening over a cash register inside the Toys R Us or the Virgin Megastore around the corner. I felt vaguely repulsed.

“No, thanks,” I said.

Her face fell. To someone walking by we might have looked like a couple having a fight. I followed her eyes, thinking maybe she’d be signaling to her husband with them. I imagined him waiting somewhere in the shadows, or peering at us through Jimmy’s window glass. She went back inside and left me under the awning in a crowd of dipso-smokers grinding gum into the sidewalk.

I came back to the table and told Ben what happened. We laughed, and he said something about the randomness of it. I pointed out the irony of being propositioned in the corporate wasteland of present day Times Square, and the historical symmetry of being propositioned outside Jimmy’s, the last of the old Times Square dives. Maybe, I said, it’s a sign that the bad old days are on their way back. If suburban housewives were on the make, I reasoned, it wouldn’t be long before the sex shops, the three card Monte men and the hustler queens were back on the take. We were getting pretty soused.

“Man, that’s crazy, but it’s a good thing you didn’t go with her,” Ben said. It was eleven now and we’d spent all our cash. The Mets were on television and we were wishing for spring. “You might have woken up tomorrow morning in an ice bath with one of your kidneys gone,” he laughed into the last of his beer. Something I hadn’t thought of.

When we got up to go. I saw her again, the blonde, still looking light and frail as paper. She was standing in front of the jukebox, next to Jimmy. He was feeding limp dollar bills into the machine, a toothpick in his teeth, and in khakis and cabana shirt it looked like maybe he was wishing for spring too. They were talking, or at least she was. Jimmy just fed singles into the slot and punched up song after song. I looked at the men standing around them trying to make the mysterious husband, but at Jimmy’s, where you could blend in by virtue of having a face and a drink to go with it, he could have been anyone.

We stood outside under the awning, Ben and I, both of us searching for the expression that would properly cap off the evening. “Crazy,” Ben said again, smiling and shaking his head. We parted and I headed towards Broadway. In the space of dim sidewalk before the blinding lights of the square, I was, for a moment, suffocated by disappointment. The openness, the anything-goes ethic of the old Times Square had drawn me to Jimmy’s, and while on the surface the blonde’s proposition seemed to be a throwback to those days, it really had more in common with the soulless, loveless, consumptive Times Square of the present. I hated her for tainting Jimmy’s with the same commercial despair that had blighted the rest of the neighborhood, if you could even call it one anymore.

I stopped in front of a table by the corner where a paunchy Chinese man was making stenciled pictures of people’s names, green dragons, ferns and red fireworks adorning the edges of the paper, all set in a cardboard matte to lend it a kind of laughable permanence. The square rose in a column of light above the huffing tourists with their shopping bags, clotting on the corners, pushing across the avenue, gawking up at the fire signs that would flash and then disappear, molecule and memory, only to begin again a moment later, an endless loop.

I thought about going back to Jimmy’s, finding the blonde and telling her off. The Chinese man at the table stopped his sketching and looked up at me. “You buy one?” he asked, and with my hands in my pockets I told him no, that I had already spent all of my money.

Brendan Patrick Hughes works in midtown and lives in Sunnyside, Queens. He sporadically blogs at brendanpatrickhughes.com.