With fall finally upon us, Manhattan sidewalks are scattered with the first swirls of fallen leaves, fiery oranges and reds kissing the tips of trees. The hot summer air is suddenly lighter, shadows longer, and the air more heavy. Full of thoughts for the winter to come, Fall wraps its arms around our bare shoulders and caresses us with it’s frosted touch.


There’s no denying that Fall — rife with cinnamon, cloves, and campfires — is the most romantic of the seasons.

Because of that, I’ve been thinking often about love. Clarity and love.


This time last year, I was in a relationship, and pumpkin patches and haunted hayrides were finding their way into my dreams. I was swept up in the idea of “Autumn in New York” with the man I so badly wanted to love, my heart trying to decipher the riddles hidden within his stoic mentality; wondering, “I know he loves me, but does he really love me?”

Fall swept me up in the idea of romance, so much so, that I think I may have missed the point.

A year has passed and I’m staring out the window at the rain, the city grey, leaves swept up by the wind only to be left tumbling into sewer grates. It smells like smoke and exhaust. Three wet birds are fighting over a soggy cigarette.


Here I am, still dreaming of those pumpkin patches (because we never went), still trying to figure out the nature of what it means to love. Somehow, I’ve convinced myself that these answers are buried in the dirt beneath the pumpkins.

You may say, “But Tess, you’re only 22. You don’t know a damn thing about love.” That’s probably true. I don’t know a damn thing about many things.

What I do know, however, is that being 22 is the best and worst time to learn about the nature of romance. As my single thirty-something friend once avowed with an absent-minded flick of her wrist, “It just gets worse from here.”

I grew up watching Friends and Sex in the City. I remember thinking then that when I got older I’d have similar experiences: Rachel getting off the plane, Big coming all the way to Paris to stop Carrie from staying with the Russian. I thought that these were the most romantic gestures in the world. Now, though, I think Rachel should have gone to Paris and Carrie should have left both Big and Russian sulking in the dust of her Manolo’s.


Living here has made me an odd melange of hopeless romantic and skeptic. After all, I was born here, so I have this sort of cultural “ha! so there” mentality that all true New Yorkers have.

I can barely commit to a coffee shop nonetheless a human being, but I go back and forth about wanting to try.

I see people kissing in the subway or getting into relationships on Facebook and I want to shake them and ask them: “How?”

It’s the same equation every time. You meet someone, go in with low expectations, and they surprise you. Suddenly you’re looking at the way their eyebrow creases when they laugh, remembering the freckle on their chest, and you wonder if maybe this is it.

I don’t even mean “it” as in forever. I mean “it” as in the moment you’ve finally met someone in this godforsaken city who isn’t going to try to make you play some sort of sordid game.

Maybe you’ve finally met the person who will continue to make you laugh for a while, someone who will be there on the hard days. Then you feel it. The moment everything starts to change.

It could be subtle like they aren’t laughing much anymore, or a grand gesture, like disappearing without a trace. They become a ghost in your life, leaving you to handle everything they left behind. Your sheets don’t smell like them anymore (a mix of Central Park and cologne) and you find yourself alone.


Maybe you’ll be lucky enough to get an explanation, which usually has something to do with their career, or maybe, just maybe, you’re the one leaving them behind. I can’t say I’m not guilty of it myself. Hell, I spent an entire weekend with someone once and decided that it wasn’t what I wanted halfway through. I even used the career excuse.


No matter what side you’re on, though, it doesn’t matter because we’re all so disillusioned with each other. I’ve seen in it in my friends too. We swipe left or right on a person and hope that whomever we match with won’t turn out to be terrible. We’re constantly rocking back and forth about what we want. About what kind of person we want to be.

This isn’t yet another article exclaiming that this generation doesn’t know how to date properly anymore. Because, frankly, no one has ever known how to date “properly.”[Is that even such a thing — to date properly? Where did it come from? What does it mean?] In previous generations, you went steady with someone in high school, were expected to settle down at 22, pop out some kids, and live a long and (questionably) happy life. There’s nothing wrong with that, per say, but it’s not what I want.

This generation of New Yorkers is the first one that isn’t inherently expected to meet these societal norms so we’re all scrambling blindly to wash off the cliches of romance and pave the way for something new.

What that “something new” is? I have no idea.

I don’t think anyone else does either. Which is why dating in New York is so difficult; because everyone is clueless. Everyone is terrified. Dating anywhere is hard but for some reason in NYC, it often feels next to impossible.


We all sacrifice so much to live here, to thrive here, and we’re all spending every second trying to make it work. Living here is a relationship in itself — there are so many compromises to make and adventures to be had that fitting in another person just seems tedious.

I know that on rainy days like this, the hopeless romantic in me wishes I had someone to wrap their arms around me, as Fall does now. I still dream of pumpkin patches and the smell of dirt beneath my boots.

Then, the sun creeps from behind the clouds, warming my skin, my heart, and I think:

“I can do this. I can do this all by myself.”

6 Comments on “The Trouble With Dating in New York

  1. My dear Tess!

    You’ll be alright. Yes, dating in NYC is hard but eventually you’ll meet someone and you’ll just know. I almost gave up on dating on my last relationship, and when I was finally content at the idea of being single when I reach 30, my current boyfriend entered into my life.

    Let things be! Hook up! Break up! It’s okay. I wish you the best as always 🙂


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