The Craziest Place I’ve Ever Been

The thing about life is that, sometimes, it demands a storyline so wild that even the best indie screenwriters would say, “Maybe tone it down a little.” And that’s how I felt one humid Wednesday night a few summers ago, standing barefoot in a kiddie pool filled with Jell-O, smack dab in the middle of a backyard in East Austin. To my left was a guy in a sequined cape trying to sell me on the virtues of kombucha (this was before it went mainstream) and to my right, a woman doing an interpretive dance with what I prayed to every deity was an actual hula hoop. In case you’re wondering, yes, I was on a date. A third one. Clearly, I’d misjudged something—or someone—along the way.

But before I get to that part, let’s rewind for context, shall we? Because every memorable fiasco has a backstory.

When Weird Is the Default Setting

Austin loves to give Portland a run for its money when it comes to the quirky Olympics. Anyone who's lived here—especially in pockets with thrift-store density and hand-poured espresso-level rents—can tell you that “Keep Austin Weird” isn’t just a bumper sticker; it’s a way of life. And I’m all for it. I once introduced myself to a musician at a farmer’s market who carried a pet rooster named Tupac. I’ve cheered at a live roller derby game that ended with a group singalong of “Bohemian Rhapsody.” So, trust me when I say: I roll with the weird beautifully. But even for me, this night felt… advanced.

There’s an old saying that how you spend your time is how you spend your life. But what’s less discussed is this: where you go really influences how you connect. Context is everything, folks. And apparently, my date—let’s call him Kyle—felt strongly that nothing revealed true compatibility like mixing performance art with gelatin-based desserts. If I’d known, I probably wouldn’t have worn my favorite gladiator sandals.

How I Got Talked Into Jiggly Performance Art

Kyle seemed normal in that charming-but-terribly-unpredictable way. Our first date was straight out of a Nora Ephron romantic comedy: iced coffees, strolling along South Congress, talking about how neither of us could commit to a houseplant but could talk passionately about the importance of composting. Date two? Equally dreamy—a dinner at this cute little spot where we shared a blue corn quesadilla and a laughably bad bottle of wine.

But then date three hit, and Kyle suggested a local “art collective gathering.” I hesitated. Art collective? That phrase in Austin has the potential for anything between tasteful pottery and rebranded Burning Man. Ever the optimist, I said, “Why not!?” Famous last words.

Twenty minutes into the backyard soirée, it became clear: Kyle was far more comfortable in this creative chaos than I was. He knew everyone. And I mean everyone. He fist-bumped the cape guy. He complimented Hula Hoop Lady on her “beautiful kinetic energy.” Meanwhile, I kept nervously circling the snack table until, inevitably, I was dragged into the kiddie pool/interactive Jell-O display. That, apparently, is what happens when you linger too long without making direct eye contact.

Readers, let me tell you, having a stranger paint your hand with Jell-O under the guise of “exploring creative textures” is not what they tell you to prepare for in dating blogs.

What I Learned While Questioning My Life Choices

Once I stopped mentally drafting my escape route (spoiler alert: I didn’t actually leave; Texas politeness runs deep), I realized this experience was less about my compatibility with Kyle and more about my compatibility with myself. People always talk about how dates test your chemistry with someone else—but rarely do they discuss how dates reveal your own boundaries, quirks, and willingness to stand in a pool of Jell-O without screaming.

Here’s what I learned that night:

  1. Say Yes… but Know Your “Hell No”
    On the surface, being open-minded is a sexy quality—everyone likes someone who’s flexible, unpredictable, down for anything. But there’s a huge difference between venturing outside your comfort zone and compromising your sense of self. For me, being adventurous didn’t mean blindly saying “yes” to an event that made me want to run home to a Netflix marathon and a bowl of carbs the second I got there. Balance is key. Give yourself permission to be discerning. Weird isn’t bad, but weird-for-you is worth respecting.

  2. How People Treat You in Chaos Says a Lot About Them
    To Kyle’s credit (or discredit, depending on your perspective), he was thriving at the art collective. Which, good for him! But while he was busy high-fiving eccentrics, I was holding onto my purse like it was a life raft and looking to him for reassurance… which never came. He didn’t check in. He didn’t ask if I was comfortable. He didn’t take a single second to include me when someone tried to explain their “spiritual Jell-O journey.” People reveal who they are in the micro-moments of discomfort. Watch for it.

  3. Your “Weird” Will Attract the Right People
    The thing is, we’re all a little strange in our own way. Personally, I geek out over obscure vinyl records, lose hours to postmodern feminist essays, and cannot resist stopping to pet every single dog I pass. I realize none of that aligns with wearable art made of recycled candy wrappers. But someone out there would swoon over me explaining why Chicana authors deserve more shelf space. Your people are your people—let them find you. Don’t contort yourself into someone else’s abstract masterpiece.

What Jell-O Taught Me About Dating

So, did Kyle and I go on a fourth date? No. Did Jell-O Girl find love? Also no. But do I regret the experience? Absolutely not. Because sometimes the craziest places—literal or metaphorical—teach you the clearest lessons about who you are and what you want.

Dating isn’t a straight path or a paint-by-numbers picture. It’s more like one of those “choose your own adventure” books: full of weird twists, occasional disappointments, and moments of pure joy. And no matter how bizarre the setting, there’s always something new to learn.

So here’s to saying yes to the unexpected, standing firm in your boundaries, and finding your version of weird that feels more like home than a backyard pool of Jell-O.