A few weeks after I moved to New York, I met up with a friend for drinks at the Lambs Club on 44th Street just east of Times Square. Joining us were a few of her friends, all coming by after work in their corporate offices — the two men were in khakis and tucked-in dress shirts, and my friend in a sharp looking blazer and skirt. I, on the other hand, did not have a job; I was sleeping on another friend’s couch as I set myself up in the city, living out of a single suitcase and hoping I could find a job before my savings ran out and I’d have to retreat back home to my parents’ house in my Virginia hometown.

I felt out of place immediately. At 27, I was almost a decade younger than my drinking companions. I was new to the city, having moved from Chicago — which is not as provincial as New Yorkers like to think it is, but is certainly a different world. And I was wearing jeans and a shirt (untucked). Although I was five years out of college and had been in the workforce, my newly unemployed life in a new, giant city made me feel like a kid again. A kid who could legally drink expensive martinis in a fancy Midtown Manhattan bar on a weekday night.

About those martinis, though. While I was more of a dive bar kind of guy, usually up for slinging back cheap bottles of beer than hard alcohol, I wasn’t a complete rube. I’d been to nice places before. Still, when the bill came I was shocked to discover that the going rate for a martini at this sort of place was nearly twenty dollars. Two of them, plus tax and tip? Over forty bucks! No one else at the table seemed to notice the expense, and so I quietly signed the little slip of paper and thought how I was about forty dollars closer to being out of money. How could I have been so stupid, to spend so much on cups of vodka with splashes of vermouth? It didn’t seem practical at all, but for some reason I felt like it was something I should want to do. The things that life casually prohibits us from enjoying are usually the things we are the most desperate to experience for ourselves.

Inside <a href="https://gothamist.com/food/inside-the-campbell-apartment-grand-centrals-hidden-historic-bar">the old Campbell Apartment</a> in Grand Central Terminal

Lee Towndrow / Gothamist

Years later, after I found my first job in New York and rotated, like a lazy susan, from entry-level to associate-level positions in media, I was working in a big, boring corporate office in Midtown. In just a few years, I had gone from an aimless, couch-surfing wannabe living and working downtown to an editor working in the city (while living like a grown-up in Brooklyn, bemoaning my daily commute). And while I still enjoyed a dive bar, and cheap beer, I also had a little money to spend. And sometimes—after long days in the office, and before the dreaded commute home–I wanted to spend that money on an overpriced cocktail. Luckily a friend of mine, Jen, worked on the opposite side of Midtown from me, and meeting in the middle of the city for a martini to gossip about our friends and enemies and frenemies was exactly what we needed to do before we went home for the night, regardless of the fact that we'd already spent most of the day doing just that over Gchat.

Every few weeks or so, the two of us would find each other miraculously free of social calls in the evening, and we’d suggest meeting up for a drink. I’d call this routine the Dumb Midtown Martini. We’d go to some bar we’d never go to on our own, or with anyone else—some place that felt a little foreign to us, where we knew we wouldn’t run into anyone we knew, because New York can be a provincial little town sometimes—and order ridiculously overpriced martinis. We’d talk about our coworkers, our days at work, what was happening on the internet that was absurd and yet still managed to hold our attention. Maybe we would order an appetizer, but more often than not we’d skip it and order the second round of martinis (Tito’s, by the way, up with a twist) so that by the end of the night our train ride home to Brooklyn would be a little bit more entertaining, or at least less grueling. (And any time an appetizer was in the cards, so was the third round of martinis.)

<a href="https://gothamist.com/food/photos-inside-the-historic-monkey-bar-a-classic-clubhouse-in-midtown">Monkey Bar</a> is another classic Midtown spot to spend too much on a Martini

Navid Baraty / Gothamist

I came to cherish these boozy evenings spent giggling about the handsome bartenders and watching well-dressed men and women wander into the restaurants to eat expensive dinners while we slummed it — sort of, the drinks were still expensive — at the bar. I still felt a little out of place in my casual work attire, but I had money that I had earned and thus earned my seat at the bar.

Over the years, that bar changed. We sat at the Algonquin during Christmastime, listening to a piano player bang out holiday tunes. We had squeezed into the crowded King Cole Bar, which was usually too busy to be really comfortable but, hey, the mural is pretty cool. I loved going to hotel bars—The Rickey at the Dream, and Park Central Hotel, to name a few—which have such odd vibes.

Midtown always felt a little foreign to me; it was a place where I went to work, not for seeking pleasure. But the Dumb Midtown Martini, despite the crass name, was the entrance fee into discovering that part of town’s charm and idiosyncrasies, a way to enjoy a place I normally associated with labor and stress and annoyance. And by the end of my eight years of living in New York (I’m sorry, I’m sorry… I moved to Los Angeles), it felt like a perfect bookend to my experience as a New Yorker: at first naive and wide-eyed, later cynical and over it—but always willing to drop a little too much money on a treat and good company.

Tyler Coates is a writer living in Los Angeles — follow him on Twitter here.

21 Club's Bar 21, in the restaurant's lobby.

Looking for a Dumb Midtown Martini? Gothamist recommends:

21 Club (21 W 52nd Street, btwn 5th and 6th avenues)

Monkey Bar (60 E 54th Street, btwn Park and Madison)

The Campbell (inside Grand Central Terminal)

King Cole Bar (2 E 55th Street, btwn 5th and Madison avenues)

The Rum House ( 228 W 47th Street, btwn 7th and 8th avenues)

The View, NYC's only rotating restaurant/bar (1535 Broadway in Times Square)

Bar Centrale, for the theater crowd (324 W 46th Street, btwn 8th and 9th avenues)

Rainbow Room (30 Rockefeller Plaza)