That Time I Tried (and Failed) to Plan the Perfect Date
Let me set the scene: It was a brisk spring evening in Brooklyn, the kind that smells vaguely of budding flowers mixed with hot garbage (a uniquely charming hallmark of New York City). I was three dates into seeing Zoe, an artist-slash-doula-slash-something-to-do-with-sustainable-ceramics—I wasn’t entirely clear, but I was intrigued. Zoe had this effortless cool about her, the type of person who probably wakes up with perfect hair and just knows which wines pair with which existential crises. Naturally, I decided the moment was ripe to dazzle her with a grand romantic gesture.
What could go wrong? (Spoiler: Everything.)
The Master Plan: High Fidelity Meets Wes Anderson
I’d put more thought into this date than I did into my senior thesis at Yale. (Sorry, Narratives of Longing in 20th Century German Literature—you deserved better.) Inspired by Zoe’s creative streak and my firmly held belief that New York is basically a playground for the romantically inclined, I mapped out what I’m convinced was a masterpiece of a date.
Phase One: A private vinyl-listening session at my favorite record store, a hole-in-the-wall gem I’d frequented since high school. I’d arranged with the owner to have the back room reserved just for us. Cozy, eclectic, and effortlessly cool—kinda like Zoe herself.
Phase Two: A sunset rooftop picnic featuring her Instagrammable favorites: artisanal bread, tinned fish (highly trendy at the time), and a bottle of obscure biodynamic wine I pretended to know about.
Phase Three: Whisking her off to an underground jazz show in DUMBO—intimate, vibey, and perfectly timed to finish just as the city lights burned their brightest.
If we’re grading this plan on paper, it’s an A+. In practice? Well, this is why you're reading this cautionary tale.
Act I: The Vinyl Fiasco
The cracks began to show early. Technically, before we even arrived. As we were walking to the record store, Zoe—who seemed a little preoccupied—confessed she’d been to eight hours of birthing classes earlier that day and didn’t know if she was up for a big evening. I—being equal parts annoying optimist and deluded captor of “romantic spontaneity”—brushed this off with a cheerful, “Don’t worry, it’s all low-key!”
Except “low-key” quickly devolved into... chaos.
The shop owner, who is normally a charming middle-aged hipster, had double-booked the back room. Instead of private vibes, we were sharing the space with a bunch of overzealous college kids who were debating Morrissey’s morality in far-too-loud tones. Zoe smiled politely but was visibly frazzled, and I panicked, trying to salvage the moment by awkwardly DJing our so-called private session myself. That’s how she ended up listening to me explain (for way too long) why Fleetwood Mac’s "Rumours" is the perfect breakup album for people who aren’t breaking up.
Zoe nodded supportively but didn’t even fake excitement when I tried to slide in a cheeky “So, how’s your appetite for drama?” Ice, meet Titanic.
Act II: A Rooftop Picnic... in the Wind Tunnel of Doom
By the time we got to my building’s rooftop for Phase Two (a ten-minute walk during which Zoe admitted she was definitely the girl in college who “didn’t get the hype” around vinyl—ouch), the sun had already dipped below the Manhattan skyline. So much for romance.
To make matters worse, the rooftop was freakishly windy. Like, Mary-Poppins-about-to-fly-windy. The artisanal bread threatened to become artisanal shrapnel, the tinned fish tins kept rolling, and the biodynamic wine tasted strongly of regret. At one particularly klutzy moment, I knocked over the glasses while trying to hold the picnic blanket down with my leg. Zoe gave me a tight smile, the kind someone gives when they’re actively questioning their life choices.
It was becoming painfully obvious that the vibe I’d envisioned—a cinematic blend of Before Sunrise and Moonrise Kingdom—now more closely resembled an SNL skit about a mediocre first date.
Act III: Jazz at Midnight? Try Jazz Never.
By the time we left my rooftop, Zoe was clearly exhausted. (In hindsight, maybe planning three back-to-back “big moments” wasn’t exactly “low-key.”) She gently suggested that she didn’t feel up for a late-night jazz set but appreciated the effort I’d put into creating a memorable evening.
I assured her it was no problem—and then immediately booked us an Uber to the jazz club because I was convinced I could still salvage the date with one last wow moment. Mistake. Big mistake.
The venue, which had been all over Instagram, turned out to be misleadingly tagged. Instead of smooth saxophones and candlelit ambiance, we were greeted by a cacophony of experimental free jazz. The kind with no discernible melody, just unhinged trumpet riffs and what I can only describe as a man yelling into a tuba.
At this point, Zoe—God bless her—broke into nervous laughter. “I don’t know what’s happening,” she said, wide-eyed, as the tuba-yelling reached an unintelligible crescendo. I didn’t either, but at least we were in it together?
The Lesson: Why Trying Too Hard Is the Worst Flex
Here’s the thing: When you’re into someone, it’s natural to want to impress them. You want to orchestrate something magical, to be remembered as the person who sparks joy and spontaneity. And while there’s value in being thoughtful, I learned the hard way that trying too hard can backfire spectacularly.
I set myself up to fail by assuming that “perfect planning” equals “unforgettable romance.” It doesn’t. Real connection isn’t about curated playlists or sunset Insta-stories. Zoe didn’t need a three-act date extravaganza—she needed someone to meet her energy, to listen when she said she was tired, and maybe order takeout so we could laugh about vinyl in sweatpants.
What I’d Do Differently
If I could go back in time (preferably via an indie rom-com montage), here’s what I’d change:
- Read the Room: The best dates don’t always have to be elaborate. They should feel right in the moment. If your partner’s energy is low, scale back. Less can be more.
- Embrace Imperfection: Missteps are inevitable. Instead of powering through like a runaway train, acknowledge when Plan A flops and be ready to pivot.
- Don’t Overcompensate: If you’re trying to make someone like you, chances are they already do on some level. Effort is attractive, but authenticity is magnetic.
- Let Things Breathe: Dates aren’t music festivals—you don’t need a packed itinerary. Create space for genuine connection to unfold.
The Ending: Not Epic, But Enough
How did it end, you ask? Well, Zoe and I didn’t end up together. But not because of the date disaster. We simply realized that while we were intrigued by each other, our lives were on different paths. Still, I’m endlessly grateful to her for teaching me something I’d been too blind to see in the past: Real romance doesn’t need soundtracks, rooftops, or tuba interludes. It happens in the quiet moments when you strip away the spectacle and show up as yourself.
So to anyone out there planning their next Big Date™: Breathe. Laugh at the awkwardness. And remember, romance isn’t about what you do—it’s about how you make someone feel. Even if it’s tinned-fish-level awkward, own it. You’ll be fine.
