Picture this: you’re standing in the type of place that feels plucked straight from a movie. Not the dreamy rom-com kind either—the Indiana Jones, “Did I just stumble onto a cursed artifact?” genre. The air smells like a mix of seaweed and nostalgia, the walls seem to close in around you, and the lighting is so dim you’d think it was designed by someone with a personal vendetta against visibility. This, friends, is where I found myself one sticky August afternoon—the craziest place I’ve ever been: a retro mermaid-themed dive bar buried under a pier in a small coastal town just outside Monterey.

Now, you might be thinking, “Chris, have you never left California? Surely you’ve been somewhere weirder?” And while I’ve been to my fair share of odd destinations (ask me about the time I accidentally crashed a wedding in Joshua Tree), this place was in a league of its own. Equal parts whimsy and a “Should I update my tetanus shot?” vibe. But let me set the scene properly.

Where the Ocean Meets the Unhinged

To get there, you first have to walk along the pier—one of those creaky wooden ones that’s seen better decades. Seagulls scream overhead, and the salty wind slaps across your face with a vengeance, like nature’s way of reminding you that you’re alive. The entrance to the bar was nearly hidden, marked only by a neon mermaid sign flickering like it’s in the final stages of life support.

The moment my friends and I stepped inside, it felt like we’d been swallowed by a time capsule. Think 1960s tiki bar, but underwater-themed: bamboo walls, glowing aquariums with dead-eyed fish, and vinyl booths bluer than a heartbreak playlist. There were velvet paintings of mermaids gazing longingly into the horizon, and a life-sized fiberglass dolphin suspended from the ceiling that I swear was judging me.

The clientele? A mix of aging hippies who looked like they’d been regulars since Woodstock, a few adventurous tourists, and—most surprising—a couple on what was clearly their first date. “Bold choice for a first impression,” I thought to myself, as the guy tried to explain that, “Yeah, I totally surf… I just don’t have a board right now.” She nodded politely, sipping a fluorescent blue drink from a pineapple-shaped cup. Respect.

A Study in Awkward Romance

Speaking of first dates: this place was chaos wrapped in kitsch when it came to romance. If I could bottle the energy in that room, it would be a cocktail of nervousness, tequila, and just a hint of questionable decisions. Everyone in the bar felt on the verge of something—either love or legal trouble. Take the couple I spied at the corner table, for instance. They were quietly laughing over a plate of coconut shrimp, heads leaning in close like actors in a Nicholas Sparks beach scene. Cute, right? Until, mid-laughter, she managed to knock over both their drinks and sent them cascading into his lap. Romantic tension? High. Courtesy napkins? Low. They laughed it off, but I knew they’d both be retelling that story to their friends later, each framing themselves as the hero.

Here’s the thing about odd settings—they strip away pretense. Whether you’re sitting across from someone new or just reconnecting with your crew, places like this force you to embrace the awkward. Sure, your date might see you at your least sparkly (quite literally, in that dim light), but they’ll also get a front-row seat to how quick you are to laugh it off. And isn’t that the real litmus test of compatibility?

Lessons from the Offbeat

Despite how strange and slightly sticky the experience was, leaving that space made me think: why don’t we embrace the bizarre more often? We default to the comfortable—trendy restaurants, sanitized coffee shop dates—but isn’t there a kind of magic in the unexpected? A chance to let your guard down among the oddities and say, “This is me, wading through the weirdness. What about you?”

So the next time you’re planning a date or even just an outing with friends, consider these takeaways I uncovered with my pineapple margarita in hand:

  1. Go where the script gets flipped. Unique locations prompt unique conversations. You might find yourself talking about that velvet mermaid painting instead of the weather, and that’s a win in my book.

  2. Humor over perfection. A place that’s unconventional can double as an icebreaker. Spilled drinks, bizarre decor—these become shared memories quicker than any five-star Yelp review.

  3. Be open to the unexpected. Awkwardness is inevitable, especially in love. But leaning into it instead of resisting often leads to bigger laughs—and deeper connections.

California, but a Remix

On our drive back to Santa Monica, I couldn’t stop thinking about that little bar tucked under the pier. Sure, I’ll always have a soft spot for California’s grandiose beauty—the sweeping coastal cliffs, the golden sunsets that practically beg to be Instagrammed—but there’s something to be said for its weirder side. The corners that feel less polished, more human. That bar was a microcosm of what makes connection so special: imperfect, funny, and strangely wonderful.

So, if someone ever invites you to a place that makes you raise an eyebrow, consider saying yes. It might not be your idea of romance (or even hygienic), but who knows? You could walk away with a hilarious story, a surprising insight into your date, or if you’re lucky, a shared moment under a fiberglass dolphin that turns out to be far more unforgettable than another perfect sunset view.

In relationships—and in life—it’s those left-turns into the unexpected that keep us curious, keep us laughing, and keep us learning. Because sometimes, the craziest places teach us the most about ourselves.