Living in Charleston comes with many perks: cobblestone streets, sunset views on Shem Creek, and the undeniable charm of running into familiar faces wherever you go. It’s got that cozy, college-town vibe — where even when you’re alone, you’re never really alone.
At first, it’s endearing. You run into your coworkers at brunch, your neighbors at the farmer’s market, and your ex… well, everywhere.
Yep — welcome to the Charleston dating scene, where the saying isn’t “small world,” it’s “you can run, but you can’t hide.”
If you’ve been in Charleston long enough to dip your toes into the dating pool, you’ll quickly realize: there’s no such thing as a clean break. Your exes will find you. Not in a scary, Lifetime-movie way — more like a cosmic prank where the city itself seems in on the joke.
Exhibit A: The Highway Walk-By
It’s been a week since the breakup. You’re healing. You’re thriving. And then — bam — you’re driving down Maybank Highway and there he is, just walking. Like a ghost of dates past.
Exhibit B: The Hurricane Happy Hour
It’s Friday night, hours after a tropical storm. You head to Share House, trying to unwind with your friends. You order an Orange Crush. And who’s standing right in front of you? None other than “Little Chico” — your once-beloved, now-barely-spoken-of ex. In your panic, you try to pivot… but end up dumping your entire drink on his white sneakers instead. Smooth.
Exhibit C: The Long-Lost Ghoster
Two and a half years post-ghosting. He’s moved away. You’ve moved on. And yet — across the dim glow of Saltwater Cowboys, there he is. He makes eye contact. He waves. He WAVES?
Charleston is small, yes. But there are times it feels like it’s shrinking just to mess with you. On any given Saturday night on King Street, you could run into four of your former flames before finishing your first espresso martini.
And then there are the moments that feel like they belong in a rom-com… or maybe a comedy of errors. Like that Tuesday morning, driving down East Bay Street. You see a jogger up ahead — hey, you used to date him! As you approach, you realize two things: 1) he’s still attractive, and 2) you’re about to hit a massive puddle.
You already know what happened. Cartoon-style splash. Head-to-toe. Direct hit.
The irony? You used to try to run into them. Back in your “scheming era,” you’d casually swing by their usual haunts, hoping fate would step in and spark a reconnection. Spoiler alert: it never worked. But now, as a reformed schemer with a therapist-approved glow-up, they keep appearing — uninvited, uncanny, and always on cue.
Is it karma? Is Charleston cursed? Is the city secretly a stage and your dating history the running gag?
Whatever the reason, one thing’s for sure: in the Holy City, the past never stays buried. But maybe that’s not such a bad thing. After all, someone’s got to keep the “GUESS who I just saw??” group chats alive and well.
And honestly? It might as well be you.
