The Time I Took "Go Big or Go Home" Too Literally

We’ve all had those bright ideas that seemed like an absolute slam dunk in the brainstorming phase but flopped harder than a bad rom-com on opening weekend. For me, that moment involved a surprise romantic gesture so outrageous, yet so ill-conceived, it still haunts me in the same way middle school dance memories linger: with a mix of cringing and an overwhelming desire to change my name and move to a new city.

Let me take you back to my late 20s, an era of overconfidence tempered by being just old enough to know better—but not old enough to actually act better.

The Grand Plan: Channeling My Inner Denzel

The moment the idea hit, I was standing in line at a Jamaican bakery, hopeful for a beef patty, but distracted by my girlfriend at the time, Nina. Nina loved grand gestures. She wasn’t about material things (though she wouldn’t protest a pair of Louboutins), but she lived for drama in the best way—think one-too-many rewatches of The Notebook, emotionally-charged poetry readings, and spontaneous make-out sessions in front of protesting onlookers.

So, in an effort to match her passion and well-read romantic ideals, I decided to plan a big surprise for her birthday: a flash mob proposal. Not a real proposal, mind you—we’d only been dating for eight months, and I hadn’t lost all of my common sense. But it was going to be an over-the-top mock proposal, a kind of inside joke that would showcase our love in a joyful, goofy way. I’d even hired a small dance troupe from Howard University to choreograph the whole thing.

I pictured myself looking suave—Denzel-in-Love & Basketball suave—dropping to one knee as Nina laughed her melodic laugh at the absurdity of it all. There’d be applause. Strangers would cheer. Somewhere, someone with an acoustic guitar might spontaneously play “Isn’t She Lovely.”

This was what I convinced myself would happen.

When Reality Pulled a Plot Twist

The day arrived, and I’d meticulously planned every detail. The flash mob would "accidentally" start while we were strolling through Malcolm X Park. Around us, people lounged on blankets, local drummers tapped hypnotic rhythms, and the smell of jerk chicken wafted from a nearby food truck. This was peak D.C., the perfect blend of cultural vibrancy that felt like home.

I was practically bouncing with excitement as Nina sipped her iced coffee, blissfully unaware of the chaos that was about to unfold. Cue the music. The Howard crew leaped into action. Strangers turned to watch. Nina’s eyes widened in delighted surprise—or so I thought.

Then the unthinkable happened. The "ring" prop I’d planted in my pocket tripped me up as I dropped to one knee. Instead of a seamless, romantic bow, I took a full tumble. My arms flailed. I landed flat on my back with what can only be described as an aggressive thud. The startled crowd collectively gasped, followed by the faint sound of someone stifling laughter.

To make matters worse, the whole dance crew misunderstood the vibe and kept going—aggressively. Imagine being sprawled on the ground while a group of enthusiastic undergrads salsa-dance around you like it’s their final exam. Meanwhile, Nina stood frozen in shock.

“I-uh, this was supposed to be funny,” I mumbled, still on my back, feeling more like a malfunctioning robot than a romantic lead. But the worst part? Nina didn’t laugh. She didn’t even smile. Instead, she whispered, “Can we talk somewhere private?”

When "It’s the Thought That Counts" Doesn’t Count

I’d expected post-mob exhilaration followed by celebratory tacos, but instead, we ended up having an intense conversation on a park bench. Nina opened up about feeling overwhelmed by the performance. “I just never asked for something like this,” she admitted, her voice treading the line between soft disappointment and cautious concern.

Now, I’ve faced some brutal critiques in my lifetime—professors who mercilessly red-penned my essays, political advisors who raised eyebrows at my stabs at humor in speeches—but this hit differently. Here I was, thinking I’d planned an unforgettable moment, and all she felt was…embarrassed.

The Lesson From the Flop

The truth is, I’d let my enthusiasm for the idea eclipse the actual relationship we had. I wasn’t listening. Nina didn’t need public theatrics or choreographed routines. She valued substance over spectacle.

So, here’s what I walked away with, and trust me, it applies beyond this specific brand of misadventure:

  1. Don’t Make It About You
    Grand gestures are only grand if they genuinely reflect your partner’s desires, not your own need to impress. My flash mob was less about Nina and more about putting on "a show" because I thought it looked good.

  2. Match the Energy
    If they’re low-key, don’t go high-kick. Relationships thrive on meeting somewhere in the middle. Nina loved meaningful, but quieter, gestures—writing her little notes or playing her favorite Anita Baker album on Saturday mornings while we made breakfast.

  3. Communicate First, Surprise Later
    Surprises are great when they fit comfortably within the tone of your connection. A little "Heads up: How do you feel about public spectacles?" could have saved us both an awkward conversation.

A Redemption Arc (Minus the Dance Crew)

Thankfully, this wasn’t the move that ended Nina and me. We laughed about it later, and I made it up to her in the weeks that followed with smaller, quieter signs of affection—whipping up her favorite oxtail dish after a long day or reading her poetry when she couldn’t sleep. The relationship didn’t last forever, but what I learned did.

Dating isn’t about pulling off the perfect scene from a rom-com. It’s about understanding and celebrating the person sitting across from you—finding aligned beats in your own version of a love song.

So, the next time you think of planning something over-the-top, ask yourself: Is this for us, or am I just directing a one-man Broadway show? Keep that answer close, and you’ll save yourself more stumbles than just physical ones.

And remember: if flash mobs are involved, always make sure you can stick the landing.