Everyone has the night where he feels like a loser. Everyone has the night where he feels jettisoned by all that is hip and cool and rockstar in the universe, left only to stand outside in the cold alone with nothing but a blackberry, a strong buzz, and a moneyclip full of cash pleading desperately to be spent on $9 beers. And since my brain has been kind enough to block out life as a summer intern, this Saturday was the first night of plebeianness I can remember. Thank God the feeling didn’t last very long.

In hindsight, it was my own fault. My friends and I were at Obivia in NoLita doing what we do best—fighting the uphill battle against a strip-steak dinner to maintain and augment our booze-high while putting on a turn of the century (21st) hip-hop dance clinic. The three of us were with girls, 8 to be precise, the majority of whom were foreign imports that clung at our every last word as if we were Manhattan’s own designated ambassadors (which we are). At one point, my friend took my hand, pointed it at a girl from Australia and said to me, verbatim, “you will fuck her tonight.” Our arms were interlocked, so I’m pretty sure she heard, and she didn’t bat an eye. All in all, not a bad scene.

But I, for some reason, was not in the mood to capitalize. I can’t exactly pinpoint why: maybe I felt the need to “branch out”; maybe it was the creeping monotony of bringing home another girl with a turquoise mini dress whose face would indelibly mark itself on my pillow in foundation; or maybe it was the Well in my drinks my cheapskate friend repeatedly insisted on panning off as Goose. But, in the moment, I felt the need for something different. Something inside of me was screaming out for a girl with a story, a girl with strife, a girl with…boots. Despite all the guaranteed ass that surrounded me, our cocktail waitress was everything I desired. Higher risk, but higher reward–I felt a shift along the curve.

She was struck-up easily. “So what passion is this job supporting?” worked like a charm—she blushed, gave me my drink, and told me she was actually a “dancer”—modern, or something. I probed just the right amount to let her tell me about her successes without getting so deep as to reveal her obvious, numerous failures. While she boosted her own negligible self-worth, she occasionally rested her hand on my chest and let her nasty, 18 hour-shift cocktail waitress hair fall into my face. Smelling Fructis + Patron was the point where I lost all rational thought.

I left my friends and followed her to the bar. I propped myself up on my elbow nonchalantly and tossed out occasional nuggets of wit while she served vodka-sodas to the retards around me. She smiled and chatted back when she could, and my confidence grew steadily.

After a while, my friends came up and informed me that they were going to the sweet downstairs bar about 10 feet away, Martignetti (Belgrade), and told me I should come. But feeling badass as ever, I told them I was definitely closing with the waitress, we were just banging out the deal terms.

I could see my buddies and the 8 girls walk away through the window, and just as I turned my head back to my waitress-love, amidst noise, I caught the phrase “So my boyfriend’s also a Banker…” . Argh.

I immediately ran to get my coat and bolted out the back door. I jogged the 15 paces to Martignetti’s and got to the bouncers just as the tail of the imported tail was making its way into the bar. I insisted that I was with the group, but it was to no avail. One of the door guys empathized, but the Chief Assbag, an obese meathead dressed in a pathetic emulation of his clientèle, did not recognize me, despite that fact that I knew his name and favorite Entourage character (Lloyd). The window that existed between my attempt to get in and the next set of girls arriving and gaining entrance quickly closed, and I was cast aside to wait along with the rest of the dregs.

I furiously texted both of my friends.

“Outside. Come get me.”

“Wtf?! Come out.”

“Send a chick.”

“Goddamn. Send a fat chick, at least.”

But it didn’t matter. I knew they couldn’t receive my SMSes in the subterranean paradise.

And even if they could receive my texts, who would respond? They were in a place where one can’t lower his drink without dipping his elbow into the cleavage of a gorgeous blond, and I was outside trying to skip over the velvet rope with fuckin Jorge and Max – Charles Schwab’s top performing young mutual fund analysts. ROAR.

I was literally pulling out money to bribe Ogre and preparing to buy a bottle entirely for myself when I saw an acquaintance from Princeton roll up. Stan Friedman was with two girls, both a bit chunky-chunk, but girls nonetheless. He sidestepped the line, and the rope was unhooked for him within seconds.

I poked my head up from behind a dude’s Zara blazer and shouted at him, “Yo Stan!”

He glanced me only for a moment, and gave me the sneer that someone who got a C+ in Econ 305 (Econometrics) gives to the better looking someone who set the curve, and I could hear his feeble mind shout proudly, “What’s the what now, bitch?!” Fuck him, and Eggers.

I folded. It was only 1:55am, but my white flag was officially up, and I had to go home. I couldn’t even get hungry it was so early, and since 2:00AM seems to be the predetermined time that every dude with a broke girlfriend whose face craters he’s trying to obscure has gotten sufficiently smashed he’s ready to stand in the middle and of the street and flail his arms to get a cab, I just decided to walk home.

Plodding along, I legitimately felt like someone had ripped out a part of my soul. Even my loafers seemed to be frowning. After two years of owning everything and everyone, the fact that I, too, am human became so apparent it knocked the wind out of me. I felt naked and exposed without my prestige cloak.

Three-quarters of the way home, more drunk off rejection than booze, I needed comfort. I untucked my shirt and growled at a dirty hipster that walked by; he almost pissed his skinny jeans. I saw a girl with an ugly thick belt over her dress and scoffed at its lack of utility; she scampered off, breaking a heel, shrieking, and falling embarrassingly in the process. And when I saw an Indian kid with long hair, I screamed at him “YOU’RE GOING ALL THE WAY SANJAYA.” He blushed, but the best part was that the Korean friend he was with (Harold, ostensibly) looked even more sad, and neglected.

At some point, I realized I was walking in circles, and I found myself back at Lafayette Street near Obivia. Officially spent and no longer competing with Dude X and his pear-shaped counterpart, I decided to get a cab. Then, out of my peripheral vision, I saw a svelte figure approaching. Its fragrance felt familiar, and when I looked over, head still hunched, I saw them–the boots.

“What happened to you in there?” she said.

I gathered myself together quickly, as if my Boss had just called me out for my screensaver actually being an Excel screenshot. “Oh nothing…just wanted to catch up with my boys,” I responded, arm out (now more confidently) to hail a cab.

“Hmph. Well, I was just telling you…” and she stepped closer. The Fructis + Patron scent was replaced by a new one: heaven (the place, not the perfume, thank God).

She was now right up against me, head craned upward so that her breathe was warming my neck. She tugged on my lapel again. “I was just telling you…that my boyfriend also is a Banker…”

And mid-sentence, she pivoted up on her toes and kissed me with a wet, half-open mouth. My arm fell.

Still floating on her toes post-kiss, she moved her mouth to my ear and tugged it playfully with her teeth, pull-starting so it was ready to listen. She finished, now whispering, “…but he works in Munis…”

We paused and chuckled together at the notion of Municipal Finance, wading in the pathetic image of some dude convinced he was saving the world, one shitty Iowa hospital bond deal at a time.

She fell to her heels, smirked, and enticed me with a cocked eyebrow and tilted head. “Wanna show me what being with a real Banker is like?”

Coincidentally, I did. And I did.

Things always have a way of working out for the privileged, eh?