What Was I Thinking?
I once thought it would be a great idea to impress a date by attempting to shuck oysters for the first time. Picture this: a breezy summer evening on the back porch of my family’s coastal home in Kennebunkport, the tide softening the rocks below, and an overconfident version of myself wielding an oyster knife like a contestant on a cooking show. I had visions of swooping in with a tray of perfectly plated oysters, a casual, “Oh, these? Just something I threw together.” Spoiler alert: that’s not how things went.
Let’s just say my “hidden depths” ended up including a sliced palm, a stain on my favorite sundress, and an unforgettable lesson in humility. But before we get to the wisdom I unearthed (along with some shell fragments), let’s start with the juicy details of my romantic misstep.
The Setup: A Maine Attraction
It all started with a guy named Nathan. He was tall, charming, and suspiciously good at quoting Hemingway—a literary Achilles’ heel of mine. We met over coffee at a bookstore in Portland, and on our second date, I invited him to Kennebunkport for what I hoped would be an effortlessly charming evening. Instead of dinner at one of the cozy waterfront taverns that, in hindsight, would have been a perfectly sane choice, I decided to create a “quintessential New England experience” at home. Because what says, “Hi, I’m relationship material” more than wrangling raw shellfish?
Admittedly, I was trying a little too hard to stay on theme. There’s something about Nathan’s type—the outdoorsy aesthete—that makes you want to lean into your salty sea captain fantasies. I wanted to be the kind of woman who casually tossed a lobster trap into the ocean before slinging a handwoven blanket over the rocks for a seaside picnic. Instead, I became the woman attempting to pry open an oyster while sweat beaded on her brow, whispering “Don’t panic” on repeat.
The Great Shucking Incident of 20–Nevermind
The seafood shop employee warned me. “Ever done this before?” she asked, holding up the steely knife with all the solemnity of a blacksmith handing over Excalibur. “It’s trickier than it looks.”
“Oh, I’ll be fine,” I said, certain that oyster-shucking was merely a matter of determination, wrist strength, and a penchant for theatrics—all of which I thought I had in spades. If movie stars could do this in rom-coms while wearing aprons and exchanging witty banter, then surely I, a native of a seaside town, could pull it off. My confidence was unmatched, and my knowledge? Limited at best.
Fast forward to Nathan and me on the porch, a tray of oysters staring up at me like smug little sea rocks challenging my very existence. I had tied back my hair, rolled up my sleeves, and donned my grandmother’s frilliest apron—because presentation matters, right? Things got off to a great start: the knife slipped, the oyster rebelled, and I promptly stabbed myself in the palm. Nathan offered to take over, but I couldn’t bear to relinquish the task. This was my moment! My maritime masterpiece!
Ten agonizing minutes later, we had two sad little oysters on a cracked porcelain plate and a bandage wrapped around my hand. Both of us were starving, slightly damp from the sea breeze, and trying to pretend this wasn’t excruciatingly awkward. Finally, Nathan broke the silence with a dry, “Well, at least we’re in tune with nature now.”
We ended up ordering lobster rolls from a roadside stand and eating them in the cab of his truck while the porch sat empty, an eerie oyster crime scene left behind. If nothing else, the lobster rolls were delicious.
What I Learned (The Hard Way)
Somewhere in the middle of licking melted butter off my fingers and laughing weakly at my own expense, a thought hit me like a wave to the face during low tide: Why had I gone to such ridiculous lengths to impress someone I barely knew? Somewhere along the line, I’d forgotten that the goal of dating isn’t to dazzle someone into liking you—it’s to spend time together and be authentic.
Here’s what shucking oysters taught me (well, besides don’t):
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Authenticity Beats Perfection Every Time
Nathan didn’t care about the oysters or the elaborate setup. He liked the fact that I laughed at myself afterward and could roll with the chaos. When we prioritize connection over image, we open the door for real intimacy. -
Don't Try Out New Skills Under Pressure
First sushi-making attempt? First time assembling IKEA furniture? These activities have no business being part of a date. Only tackle ambitious endeavors if you know you’re confident enough to laugh through inevitable hiccups. Otherwise, it’s just secondhand embarrassment waiting to happen. -
Impressing Someone Isn’t About Grand Gestures
You don’t need a lobster trap and a seagrass table runner to show someone what makes you unique. A casual walk along the beach with hot dogs and string lights can be just as romantic—possibly more so, since hot dogs don’t involve sharp instruments and a high risk of infection. -
It’s Okay to Let Go
When something’s not working (say, shucking your eighth oyster only to discover it was already half-open), don’t hang on too tight to the Plan A version of your evening. Some of the best memories come from embracing imperfection, whether that means swapping fine dining for fried food or just laughing through the mess.
The Aftermath: Not a Total Loss
While the evening leaned more “Tells this story at parties” than “He’s the one,” Nathan and I did manage a few more dates. We hiked, visited a local gallery, and ate food that didn’t involve me handling sharp objects. Ultimately, the romantic spark we’d first shared fizzled, but we parted on good terms. We still follow each other on Instagram, and every so often, he’ll post a photo of a raw bar with a cheeky oyster emoji in the caption. We love a man committed to a lifelong bit.
Wrapping It Up (Like a Lobster Roll)
Not every dating misstep comes with such a literal pain point, but they all help us to uncover something valuable—whether it’s the importance of authenticity, the humor in our mistakes, or simply why oysters are best left to the pros. We all have a wildly overambitious evening lurking in our pasts, but that’s part of what makes dating such an adventure.
The next time you’re tempted to juggle live lobsters or reorganize your entire personality to impress someone special, remember: the best dates aren’t about spectacle; they’re about connection. And if things go sideways—and they will—you’ll have one heck of a story to tell. Just bring Band-Aids. Trust me on that one.
