The Most Awkward Date of My Life (and How It Made Me Better at Online Dating)
Okay, let’s talk about it. You know the kind of date you still cringe about 10 years later? The one that feels like an outtake from a low-budget romantic comedy—except there’s no rom-com payoff at the end, just you stress-eating fries in your car while replaying the disaster in your head? Yep, we’re going there.
For me, that date happened on a balmy July evening—a night so sticky-hot, even the Grand Strand’s breeze couldn’t help. I’d swiped right on a guy I’ll call “Boardwalk Ben.” His profile painted a picture of a witty, ocean-loving local who layered sandcastle puns into his bio (“Looking for my partner in grime.” Honestly? 10/10 for creativity).
I figured: What could go wrong? Spoiler alert—everything. But that one mortifying night became the moment that changed everything about how I approached dating, especially online. Buckle up—it’s story time.
Act I: The Date That Was DOA
Ben and I met at a beachfront seafood shack, because nothing says “getting-to-know-you” like haphazardly cracking open a crab leg. Within five minutes, I realized the magnetic, zippy conversationalist from the app was… not here.
Instead, I was seated across from someone gazing at his phone like it was the love of his life while mumbling vague responses to my questions. Did I misremember his profile? Was this actually an out-of-town tourist who’d just stolen Boardwalk Ben’s identity? Desperate to salvage the night, I pivoted. “So, tell me about your favorite boardwalk memory!” I chirped, channeling full faux-boho optimism. (Perhaps the humidity cooked my common sense.)
His response: “Boardwalks are okay, I guess. But, uh, I’m more into Reddit debates.” Cue the sound of seagulls cackling at me in the distance.
As the night dragged on like a Netflix queue full of bad recommendations, I realized my dating strategy—if you could call it that—was cracked. I’d focused too much on crafting a perfect profile to pull dates and hadn’t thought nearly enough about how to connect (or, in this case, how to disqualify Ben-level boredom before wasting time sashaying into seafood purgatory).
That humid night ended with me power-walking to my car while texting my best friend something to the effect of, “Do I fake my own death or just block him?”
Act II: What I Learned While Overanalyzing in Sweatpants
In true millennial fashion, I turned to my coping trifecta of Spotify breakup bops, soft-serve ice cream, and overthinking. When the brain fog cleared, here’s what I realized:
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Your Online Dating Profile is Your Opening Scene, Not the Whole Movie:
I’d poured so much energy into crafting the snappiest bio and eye-catching photos that I forgot to leave room for authenticity. Sure, I wanted to showcase “cool, adventurous Kaylee” (she snowboards once every three years and loves beach sunsets), but where was space for “sweatpants-wearing, book-devouring Kaylee”? Fake perfect vibes attract other fake perfect vibes—it’s like putting on the wrong cologne and wondering why you’re attracting mosquitoes, not dates. -
Details Are Everything (Even the Mundane Ones):
While editing my dating profile mid-spiral, I swapped clichés like “loves long walks on the beach” (#eyeroll) for actual snapshots of me. “Happiest with my nose in a book and a dog at my feet” wasn’t groundbreaking, but it was me. Authentic details help your profile do the heavy lifting of weeding out people who are just Not Your People. For example, if they don’t vibe with my annual Nicholas Sparks hate-watch tradition? Sorry, it’s a dealbreaker. -
Swipe with Purpose, Not Panic:
Why did I swipe right on Ben? Because I was doing exactly what I used to do on the boardwalk arcades as a kid—throwing quarters at every claw machine without a strategy and getting annoyed when I just got a plastic whistle. When online dating, it’s about being intentional instead of mindlessly swiping for dopamine hits.
Act III: How to Turn Profiles into Partnerships
Alright, if my sweatpants revelations can make one less person suffer through a “date from base camp of Mount Cringe,” they’ll have been worth it. Here’s how my lessons translate into actionable tips for your dating profile:
1. Use Photos That Feel Like Your Life—No Filter Necessary
Overly posed pictures are so 2014. Save the photo dump of you skydiving “that one time” for Instagram. Instead, showcase pictures that mirror who you genuinely are: maybe laughing with friends at trivia night or sipping coffee in your happy place. This isn’t about “curating perfection”—it’s about giving people a quick, honest window into your world.
Tip: Don’t underestimate props! A photo that casually includes your favorite book, your rescue dog, or your surfboard can speak volumes without saying anything.
2. Write Like You’d Text Your Best Friend
Forget the pressure to be clever—it’s about being clear, concise, and you. Think of your bio as the highlight reel of conversations you actually want to have. Share three facts or quirks that make you sparkle. Example:
- “Can quote every line from The Office—try me.”
- “Looking for someone who thinks board game night = date night.”
- “My dog’s name is Captain Waffles. That should tell you everything.”
See what I mean? Authenticity > generic buzzwords.
3. Call Out Key Compatibility Clues
Attraction is great, but shared values are where the magic really happens. For me, it’s the little things: someone who’ll turn off their phone over dinner, respects beach cleanup days, and doesn’t flinch when I reference Southern Gothic novels like it’s completely normal (because it is).
Pro-tip: Make your profile a magnet for the things you want! Toss in practical clues about your favorite date vibe (“Let’s hunt for used bookstores and pet stray cats”) or your deal-breaker (“If you think flip-flops count as formal wear… no.”)
The Happily-Ever-Yet
Did I ever see Boardwalk Ben again? Absolutely not. But his ambivalence was the pivot I didn’t know I needed. That disaster of a date taught me to stop romanticizing the romanticized. Dating isn’t about polished perfection; it’s about messy, human connection with people who value you for exactly who you are (weird dog nicknames and all).
Stepping away from the filters and the swipe-right frenzy, I found the courage to embrace my quirks unapologetically. And wouldn’t you know it? The moment I got real about who I was, someone started trying to win me over with a book recommendation I hadn’t heard of—a real partner in grime to the real me.
So, to whoever’s reading this: please skip the sticky seafood shack date with your own version of Boardwalk Ben, and spend that time reimagining how you show up online. (Also? Always bring fries to debrief dates with your friends. That part of the night? No regrets.)
You’ve got this—and hey, don’t sleep on the Captain Waffles trick. Trust me, it works wonders.
