The Worst Date of My Life: A Miami DJ, His Arrogance, and My Last Shot at Summer Romance

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March 2025—oh, how I wish I could forget it. But unfortunately, I can't, because it was the month I had the worst date of my life. Yes, that’s right. The worst. Of my entire life. And I’m not talking about the usual bad date stuff: awkward silences or terrible food. No, this one was an entirely different brand of disaster that had me questioning every decision I’ve made up until that point. And if you’re thinking I’ve learned my lesson and will never attempt a Miami summer romance again, well... you're absolutely right.

This nightmare started, like most modern-day mishaps, on a dating app. I was in the mood for a little excitement, some good conversation, maybe a flirty moment or two. You know, the stuff that happens when you get an itch for something new. So, there I was, casually scrolling through profiles, when I stumbled upon him. His profile screamed "mysterious artist," which, to be honest, was kind of my thing. And let’s face it, who doesn't want to date someone who claims to be an “artist”? He was a DJ (and yes, he made sure I knew it right away), and something about his pictures caught my attention. They weren't like the finance bro profiles I usually swipe left on. They were a little different, a little cooler. He wasn’t wearing a suit and tie; he was behind a DJ booth, looking intense, making his whole “I’m too cool for this” vibe clear. I thought, “Hey, let’s go for something different. Could be fun.”

Our conversation started as any other dating app chat does—small talk about music, hobbies, and what we liked to do for fun. As the conversation unfolded, he casually mentioned how he “wasn’t like the others,” that he “couldn’t deal with the average crowd,” and how “Miami’s nightlife was kind of tame for him.” Uh, okay. Not the humble brag I was expecting, but I let it slide. This guy was obviously full of himself, but maybe I was just being too harsh. I mean, maybe I was in the mood for someone who wasn’t a carbon copy of my usual type, the finance bros who drone on about their portfolios and golf swing stats. And besides, he was cute enough. He could buy me a drink and I could judge from there, right?

So, we agreed to meet at a trendy bar in Wynwood. Of course, it was one of those places where the ambiance is more important than the actual food or drinks, but I thought, why not? I was ready for a night of fun. He texted me as I arrived, and I was greeted by a vague message: "I’m outside, don’t get lost." Um, okay, I won’t. But thanks for the clarity. I walked up to him, and... let me tell you, the vibe was off from the start. I’m not sure what I was expecting, but this guy wasn’t even looking up from his phone when I walked over. Like, is this supposed to be charming? I wasn’t sure. But I smiled, hoping maybe he was just busy.

“Hey,” I said, offering a friendly smile. He barely acknowledged me, muttering something about “just being in the zone” and how he’s always “working.” Um, okay, buddy. We’re on a date, not at your "studio."

The night only went downhill from there. As we made our way into the venue, it was clear this man didn’t know what “normal” human interaction was. He began talking at me—not to me—about how he was a “visionary DJ” and how he was basically destined to change the Miami nightlife scene. I nodded along, pretending to care while secretly wondering how quickly I could escape. The kicker? He dropped his “humble” line about his “connections” and how he was friends with “the people who run Miami,” which, to be honest, I didn’t even understand. Was I supposed to be impressed?

And then it happened. The thing that solidified this date as the worst I’d ever been on. After a few more attempts to engage in conversation, he casually said, “So, I’m gonna need you to pay for parking. It’s Miami, you know how it is.” Wait, WHAT? He asked me to pay for parking? As if I wasn’t already reeling from his condescending attitude and utter lack of charm. I was speechless. Did he think I was there to support his supposed artistic genius by literally giving him money for a spot he’d probably never have to worry about in his “billionaire DJ” world? But no, this guy was too busy being "too cool" to even offer to cover parking. So, there I was, out $10 for parking just to keep the night going.

But it didn’t stop there. No, of course not. After I grudgingly paid, he went on to make more statements about his “crazy connections” in the industry, while I sat there, trying not to strangle myself with my drink napkin. At one point, I actually tuned out entirely and started making mental notes for this very article. "Worst date of my life," was already written in my head.

By the end of the night, I couldn’t get out of there fast enough. He offered me a handshake (yes, a handshake!) as though he was doing me some kind of favor, and I was out the door before he could say “See you later.” I didn’t get a text, I didn’t get an apology—hell, I didn’t even get a “thanks for covering my parking.”

And that, ladies and gentlemen, was the last time I ever sought out a “Miami summer romance.” It wasn’t just that the date was awful, or that I was stuck with someone who thought he was God’s gift to nightlife—it was that this man couldn’t have been more out of touch with basic human decency. You know what’s sexy? Paying for parking, being kind, and treating someone with respect. But no, this DJ didn’t get the memo.

So here’s my advice: Ladies, if you meet a guy who makes you pay for parking on a date, run. I don't care if he’s a DJ, a millionaire, or a self-proclaimed “visionary”—if he can’t even cover parking, he’s probably not worth your time. I’m hanging up my summer romance dreams, because clearly, not everyone is ready for a real connection. And that’s my new rule. As for the DJ? He can stay in his studio, because I’m good. Very good.