Okay, so I have to preface this post by saying: this is one of the most New York things that has ever happened to me.
Also—I swear this kind of thing doesn’t normally happen when I go out on a Tuesday night just “for one drink.” But then again, I did say that the night I wound up dancing on a float in the Pride parade with Liza Minnelli. (Another blog post, another time.)
Let me just tell you everything… from the top.
Tuesday Night Drinks: A Plot Twist Waiting to Happen
So my friend Sophie texts me around 6 PM: “Drinks in SoHo? That teeny wine bar on Sullivan?”
I’m always down for anything involving rosé and boutique lighting, so I threw on my Marni trench (it was just chilly enough to pretend it was fall), grabbed a vintage clutch (yes, Chandler, the one that looks like a baguette), and headed downtown.
She was running late (classic Sophie), so I decided to pop into this unmarked black door next to the bar.
Yes. I don’t know why I did it. Curiosity? Thirst? Destiny?
Enter: The Speakeasy I 100% Was Not Cool Enough For
I pushed open the door thinking it might be, like, a coat check? Or a bathroom? Turns out… it was neither.
It was a speakeasy. A real one. Velvet curtains, Art Deco chandeliers, jazz music playing softly—think Zelda Fitzgerald’s living room meets Wes Anderson.
And here’s the towncar cherry on top: the hostess looked me up and down and said, “You’re early. They’re setting up for karaoke.”
…I was early? For something exclusive that I absolutely had not been invited to? Very me.
Now, a reasonable, fashionable adult woman would have said, “Oh, sorry!” and backed away slowly.
But if I’ve learned anything from living in New York (and from Monica after a bottle of Pinot Grigio), it's this: walk in like you own the building and wear your confidence like it's couture.
So I smiled, said “Great, I’ll grab a table,” and waltzed right in.
The Broadway Star (Who, Spoiler Alert, Can Sang)
As I’m sipping something the bartender called “The Lavender Uprising” (I didn’t ask—I just drank), more people started filtering in. Glamorous people. Theater people. Glossy, eclectic, high-cheekboned people.
And THAT’S when I saw him:
—gold velvet blazer
—iconic dimples
—actual legend from a Hamilton revival (IYKYK)
Let’s call him “Theo,” because I’m still not entirely convinced I didn’t hallucinate the whole thing.
He gets up to sing "Benny and the Jets" and I die. Dead. Passed. Buried. Resurrected by the first piano key.
He sounded like butter had a baby with Barbra Streisand’s vocal cords.
And then—get this—he looks out, points directly at me (ME?!), and says:
"Let’s do the next one together!"
I nearly dropped my Lavender Uprising on the floor. Instead, I nodded, calmly dabbed my lip gloss I DID NOT NEED, and joined him on stage like I had been waiting for this moment my entire life (reader, I had).
The Song? “I Got You Babe.”
The duet was pure magic. I was Cher. He was a musical theater Sonny. Was my pitch good? Who cares. Did I harmonize? Let’s say emotionally, yes.
The crowd went WILD—aka a polite smattering of applause and one woman in a feathered headband who whispered “iconic” under her breath.
After we sang, Theo hugged me and said, “You’ve got stage presence.”
Brb, calling my Drama teacher from high school to update her on my blooming career.
What I Learned from Singing Karaoke in a Mystery Speakeasy
- Always say yes (within reason, and preferably within walking distance of rosé).
- Fashion confidence translates to life confidence. Don’t question why you belong somewhere. Just order the cocktail and act like it has your name on it.
- Everyone—and I mean EVERYONE—should sing with a Broadway star at least once. Even if you’re tone-deaf. Especially if you’re tone-deaf.
- New York City is wild and chaotic and exhausting and expensive… and it still manages to surprise you when you least expect it.
Final Thoughts (and One Slight Regret)
The only thing I regret is not taking a video. Or his number. Or the recipe for the Lavender Uprising (because I would literally sell my best pair of Jimmy Choos for that drink).
But maybe that’s the beauty of it all. Sometimes the best New York nights are the ones you can't recreate.
You just have to be brave enough to walk through the wrong door.
Until my next accidental adventure,
xoxo
Rachel 💋
PS: If anyone knows a Theo who wore a gold velvet blazer in SoHo last Tuesday… call me.
