I swear I did not plan this. One minute I’m trying to escape the chaos of SoHo on a Saturday (you know, when everyone and their mother decides it’s the perfect day to brunch, shop, AND declare their love in the middle of Prince Street), and the next, I’m toeing off my heels on the edge of a rooftop in the East Village, holding a pink margarita, and singing Happy Birthday to someone named… Kyle?
How I got there is kind of a classic Rachel story.
The Day It All Spiraled—In a Good Way
Okay so, let me set the scene: it’s 4:30 PM and I’m all dolled up in a vintage Marc Jacobs slip dress because I heard there was a vintage pop-up on Bowery. Spoiler: there was not. My phone died. The pop-up was apparently last Saturday. Or maybe February? Who knows. All I know is I was stranded and very much not going to take the subway in heels.
So I wandered. “Wandered” being a fashionable pivot through three coffeeshops (none with outlets), one misadventure into a crystal shop ("Your aura is chaotic today" — tell me something I don’t know), and finally, into a tiny side street I swear I’ve never noticed before. And trust me, I notice things.
And then I saw it: a discreet little staircase with a velvet rope, a sleepy pitbull curled up next to a cooler, and a guy in a Hawaiian shirt looking like he was about to say, “Are you on the list?”
Which he did. To which I said — and I’m proud of this one — “I’m Rachel Green. I should always be on the list.”
Spoiler: I Was Not On the List 😅
But he laughed. And said Kyle just told people to “bring cool humans.”
And apparently, I gave off “cool human with mysterious energy” vibes, which I’m choosing to take as a compliment and not a backhanded way of saying “confused and lost girl with shiny earrings.”
Climbing those stairs was literal magic.
The Rooftop: A Fever Dream in Fairy Lights
Upstairs was a hidden little paradise — string lights, old mismatched furniture that looked like it had very good stories to tell, plants sneakily trying to take over the place, and an honest-to-God disco ball hanging from a plumbing pipe. The music? Some weirdly perfect mix of Stevie Nicks and thumping house beats. I don’t know how it worked, but it did.
There were people sketching each other (I did not volunteer), people building a cheese tower (not a board — a tower), and someone DJ'ing with vinyl wearing a beret and absolutely no irony.
And there, in the middle of it all: Kyle. Wearing a sash that read "Birthday Icon" and turquoise loafers.
At some point I was handed a pink margarita garnished with dried rose petals (did it taste like soap? Yes. Was it divine? Also yes), and then I was sitting on a vintage trunk between a guy who makes “emotional succulents” and a woman freelancing as a perfume griot. (She read my “scent aura” and said I reminded her of vintage leather car interiors… which is maybe the sexiest thing anyone’s ever said to me?)
And then we sang. So loudly. Off-key. It was ridiculous and weird and so New York.
“At one point, I looked around and thought—Wow. This is why I didn’t stay in Long Island.”
Things I Learned That Night
- Always say yes to a rooftop. Even if the staircase is questionable.
- Rose petals in cocktails are aesthetic lies — they look dreamy but taste like lotion.
- New Yorkers are absolute weirdos and I love us for it.
- A dead phone doesn’t mean the night is over — sometimes, it’s just starting.
- Strangers can sometimes become your favorite part of the day.
- Kyle knows how to throw a phenomenal birthday party.
My NYC Moment of the Week
Every week, I’m trying to collect these little NYC sparkles — those vaguely cinematic, possibly chaotic moments you only get if you live here. This was mine: wrapped in twinkle lights, eating mystery cheese, dancing to Fleetwood Mac remixes under the skyline, laughing with strangers who felt oddly like home.
Listen, I didn’t find vintage boots that day. But I found joy and cheese and rooftop magic.
And Kyle.
(If you’re reading this: Happy Birthday again. I still have your plastic glitter flamingo. Oops.)
xo,
Rachel
