Date: June 7
Hi! Okay—so I'm not proud of this.
Well…
Actually, I kinda am?? And I promise, it’s not as bad as it sounds. (Okay, maybe it is. But also: rooftop.)
Let me tell you a story—grab a latte, kick back and please don’t judge me until you’ve seen the view.
The Meet-Cute: Featuring Cold Brew and a Little Bit of Guilt
About a month ago, I was browsing the skincare aisle at that big Sephora on 34th when I bumped into a guy holding The Ordinary serum like he actually knew what it did. Naturally, I was intrigued.
He looked like a finance guy—I know, I know. But he had this cute, nerdy thing going on and he asked me if niacinamide would help “fix his face after the last company off-site in Tulum.” I figured, okay, he's got a sense of humor. Also, dimples.
So we exchanged numbers. His name? Upstate Drew.
Spoiler alert: his name is just Drew, he’s from New Rochelle, and he owns, hands-down, the best rooftop in all of Murray Hill.
Let’s Talk Rooftop
Oh. My. God.
I’m not talking about one of those rickety fire escapes with a folding chair and an old HVAC unit. This was a legitimate terrace. Like, landscaped and curated. There were string lights, modern patio furniture in an actual color palette, and—wait for it—a full bar cart.
He even had those misty spritzer things to cool you down on hot nights. Like you’re in Ibiza. And let me remind you—we’re in Murray Hill.
Every five-star rooftop in Manhattan was suddenly irrelevant because I knew the code to Drew’s building.
So yes. I may have gone on six dates I wasn't fully emotionally invested in because I wanted to watch the sunset with a plastic cup of overpriced rosé and a view of the Empire State Building.
And you know what?
No regrets.
Reasons I Stayed a Little Too Long
- He had a golden retriever named Bark Ruffalo. That’s a level of whimsy I respect.
- His bar cart included lavender-infused gin. I’m not even a gin girl but I became one very quickly.
- The rooftop was peak golden hour magic. You could see the Chrysler Building sparkle.
- He bought vegan charcuterie when I said I was “basically, sort of, plant-based on weekdays.”
- There was a hammock. Like… just anchored between two walls, as if gravity personally owed him a favor.
But Also, You Can’t Fake Chemistry
Let’s be honest—conversations kept… looping.
He had one anecdote about accidentally investing in crypto at work and he used it on three separate dates. I wanted to be present. I really did. But my mind was always wandering—not in a deeply romantic daydream kinda way, more like “how soon is too soon to ask if I can just go up to the roof by myself?”
Eventually, you go from, “He’s so sweet,” to “I think he just apologized to his doorman for *me being there.*”
So yeah. One day, I politely ended things.
But not before one final rooftop night, alone, with a cheese board and Taylor Swift playing on Drew’s Bluetooth speaker. I left behind a bottle of prosecco as a thank-you.
(Mostly because it didn’t fit in my tote.)
What I Gained
Okay so maybe the relationship fizzled—but New York? She delivered.
I got:
- A newfound love of rooftops (no surprise).
- A better understanding of when you’re into the idea of someone versus who they actually are.
- The coordinates to a Duane Reade that sells the good claw clips.
- A reminder that it’s okay to want something beautiful—even if it’s fleeting.
“Not everything has to last forever. Some things are just meant to sparkle for the summer and then disappear—like rooftop twinkle lights and guys named Drew.”
Currently…
Right now, I’m writing this from a tiny café in the West Village, sipping an oat milk cappuccino next to a pink peony I maybe stole (borrowed!) from a nearby stoop. My phone is blowing up because Phoebe just tagged me in a picture from our SoHo thrift day and I’m wearing a hat I regret buying.
Carrie Bradshaw once said something about relationships being like New York apartments—hard to find, mostly walk-ups, and kind of expensive to maintain.
But honestly?
Sometimes, it’s worth the climb for the view.
Until next time—if you're in Murray Hill and spot a rooftop with lavender gin and a hammock… wave hello for me.
xo,
Rachel 💋
