The Craziest Place I’ve Ever Been

Starting With a Bang: That Time I Dated a Guy in a Waffle House Parking Lot

It was a crisp Friday night in July—yes, July can be crisp in Tennessee if you catch an especially blessed night—and I found myself on a “date” that didn’t just toe the line of wild, it kicked it clean off the map. You see, I wasn’t in a dimly lit wine bar or strolling with blushed cheeks through a botanical garden. Nope. I was smack dab in the Waffle House parking lot, perched on the tailgate of a beat-up Chevy, sharing a plate of scattered, smothered, and covered hash browns with a man who insisted his nickname was “Tater.”

To be clear, this wasn’t supposed to be the plan. We’d met at a mutual friend’s backyard concert-slash-cookout—classic East Nashville through and through—and I’d agreed to let him take me out because he had this infectious laugh and a deep Southern drawl that could make any Dolly Parton song sound like scripture. But when his original dinner reservation fell through (a scheduling oversight, he claimed, though I had my doubts), his Plan B turned out to be something of a cultural pilgrimage.

“This is where the magic happens,” Tater had said, gesturing toward the greasy glow of the 24/7 diner behind us. I wasn’t sure if he meant midnight waffles, first dates, or the occasional post-bar brawl. Maybe all three.

Waffles, Wisdom, and Why Sometimes “Weird” Works

At first, I wanted to bail. What kind of guy thinks fried breakfast at 9 p.m., surrounded by moths, neon signs, and questionable life decisions, screams “romantic evening”? But then he handed me a plastic fork, grinned like a mischievous twelve-year-old, and asked, “What’s the craziest thing you’ve done lately?”

Caught off guard, I stayed. And, reader, that decision turned into an unexpectedly great evening—and gave me a lot to think about afterward.

Here’s the thing: The Waffle House parking lot humbled me in ways a five-star restaurant never could. Nothing forces you to drop pretenses quite like trying to impress your date while dodging mustard stains. Between bites of buttery toast and deep, unprompted revelations about our favorite road trip songs, I realized something crucial: It’s not about the place, it’s about the person and the vibe they bring.

There’s a surprising charm in doing something so absurd—so outside the bounds of “acceptable date norms”—that you feel yourself relax. Should a first date be slightly uncomfortable? Maybe. But it should never be boring.

What Makes “Weird and Wonderful” Dates Stick

Unconventional dates, like mine with Tater, set themselves apart for a reason. Let’s break it down:

  1. Comfort Kills Chemistry:
    Sharing a plate of hash browns isn’t exactly the stuff of Pinterest date boards, but it pushed me to ditch that inner monologue of, “Do I look like I have it together right now?” Spoiler: I did not, but neither did he. And that’s what leveled us.

When you strip away the “polished” layers—silk blouses, curated playlists, conversations like bad TED Talks—you find out who someone really is. Do they have a sense of humor? Can they roll with the punches? Tater might’ve been eccentric, but he was unapologetically himself, and that’s oddly magnetic.

  1. Shared Stories = Instant Bonding Material:
    Years later, I hardly remember the downtown dinners I’ve been on, polished as they were. But the details of parking lot confessions and lukewarm waffles? Burned into my brain forever.

A wild or unexpected setting creates stories, and stories become the foundation of early connections. You laugh about it, you call back to it, and suddenly you’ve built a little emotional shorthand.

  1. It Forces You to Be Real:
    Nothing screams “authenticity” quite like borrowing a napkin to catch grease on your chin while a man nicknamed Tater serenades you with a surprisingly soulful rendition of “Jolene.”

Lessons Learned (Over Hash Browns, Naturally)

Now, I’m not saying everyone should drop their dinner plans and head to the nearest late-night diner. (Though for the record, Waffle House does an unbeatable pecan waffle.) But I am saying there’s power in letting go of your expectations and being open to the weirdness life throws at you.

Here are a few takeaways from my parking lot escapade that might help you keep things fun—for yourself and your potential partner:

  • Loosen Up Already: We get so caught up in curating the perfect date that we forget to do the actual connecting part. Spark doesn’t come from romantic candles or whatever Spotify suggests as your “First Date Playlist.” It comes from being present. Choose someone you can laugh with over someone who plans the itinerary of the century.

  • Find the Humor in It: If your first instinct is to catastrophize (like I did at first), stop. Your nerves aren’t there to sabotage you—they’re there to remind you that you’re doing something meaningful. Take that energy and channel it into laughing about how ridiculous the situation is instead of running from it.

  • Judge the Person, Not the Plan: Did Tater plan poorly? Sure. But the guy listened when I talked, loved his dog (shoutout to Sadie, his blue heeler), and had a kindness about him that outweighed the misstep. Look for the human behind the hiccup.

Would I Do It Again?

Though Tater and I didn’t end up as a forever thing, that date gave me a story that outlives most relationship endings. More importantly, it reminded me to stop being so precious about the “perfect” date and instead focus on finding the perfect kind of fun.

So, if you’re reading this while swiping through a curated dating app bio in search of someone whose idea of adventure doesn’t include deep-fried carbs, let me offer you this: Take the chance. Say yes to something that isn’t “your normal.” You just might find that the craziest place you’ve ever been isn’t a location at all—it’s a feeling of actually, fully, foolishly connecting.

Worst case, you’ll walk away with a good story. Best case? You’ll find your Tater.