My Big Fat Misadventurous Dinner Date

Let me start by saying this: I had good intentions. They say the path to hell is paved with those, and as it turns out, so is the path to a thoroughly disastrous first date.

A few years ago, I decided I’d take a girl—let’s call her Ana—out to experience the pinnacle of Cuban cuisine. You know, show her my roots. This wasn’t your Miami touristy version with fried plantains brought out under strobe lighting. No, I wanted this to feel like a Christina Aguilera belting-out-“Mi Tierra” level of authenticity. We were in Chicago at the time, far removed from Miami's familiar pastelitos and cafecitos, so I’d researched high and low to find the Cuban spot. I had one shot to impress her, and I aimed high. Spoiler: Maybe a bit too high.

Act I: The Perfect Plan (Or So I Thought)

Ana was someone who knew her way around good food. When she talked about wine pairing notes, I just nodded like the supportive boyfriend in a rom-com who has no clue what tannins are. It was adorable when Paul Rudd did it, so why not me?

I wanted this date to be a humble brag about my culture: the ropa vieja, the yuca con mojo, the soul of Cuban cooking that was simmered and slow-cooked in abuela kitchens and family gatherings. I could practically hear my abuela’s voice cheering me on from the Miami sidelines: “Sí, mijo! Show her where you come from!”

So, on a cold February evening, I booked us a table at a tiny, off-the-beaten-path Cuban restaurant that had rave reviews and one of those menus where everything has five adjectives. Chic. Authentic. Really expensive. Because what screams “I have my life together” like a candlelit dinner at a place where the waiter disapproves of how you pronounce malanga?

Act II: Let Chaos Reign

The night started great. We walked into the restaurant, escorted to a cozy little table near a string of fairy lights. It was straight out of a Pinterest board: romantic and intimate, with just the right amount of “I’m trying but being casual about it.”

Then, our waiter recommended the tasting menu. “It’s a beautiful journey through Cuba’s rich culinary legacy,” he said, which sounded like a solid choice for someone trying to impress a date and an imaginary panel of Cuban ancestors at the same time.

But here’s the thing about tasting menus—they’re a gamble. And, like foolish optimists at a casino who don’t know the house always wins, I said yes. First came the appetizers: pastelitos that were somehow both too sweet and too dry (like a text from your ex after a long silence). Then came the yuca fries. Tragically, they ate like sad beige sticks of regret.

The kicker? Ana, bless her foodie heart, noticed immediately. She took a courteous bite of her food, smiled at me like a champ, and said, “This is interesting!” For those who don’t know, “interesting” is the dating code word for “I’m too polite to tell you something tastes like cardboard.”

By the time the arroz con pollo arrived, we both knew this was a sinking ship. There was no salvaging it. I could no longer pretend the flan wasn’t aggressively eggy or that the mojitos weren’t somehow both watery and sharp. The dream of impressing her? Dead on arrival—covered in too much overcooked black bean sauce.

Act III: My Internal Meltdown, External Cool

You have to understand: for someone who grew up in a loud Cuban family, pride in your food is like pride in your flag. Every dish is an edible love letter to your identity. So sitting there with subpar plates of what should’ve been my cultural magnum opus felt like someone had AutoTuned Celia Cruz.

I could feel myself spiraling. Ana, being perceptive, noticed my mood shift from suave-Confident-Martin to anxious-Are-You-Still-Having-Okay level 10. She dipped her croqueta into a sauce that, honestly, looked like it came from a gas station ketchup packet, and as she chewed, she gently asked, “You okay?” That’s when I realized—I was the mess here, not the yucca fries.

Act IV: What I Learned About the “Perfect Date”

Here’s the thing no one tells you about planning a date: trying too hard is the same as trying wrong. I wanted Ana to not only like me but to like where I came from—to have some transcendent “Eat Pray Love” experience with my culture. But at its core, dating isn’t about putting on a Broadway show. It’s about connection.

That night, my focus had been all wrong. I’d put so much pressure on the plan that I forgot about the fun—the part where you laugh over how bad the food is, or how the waiter has been pretending to like you but is actually plotting your demise because you ordered “Cuba Libre” too enthusiastically. (In my defense, it was charming at the time.)

What saved the date wasn’t the food or my awkward half-apology about the “authentic Cuban experience.” It was Ana herself. She picked up her rock-like pastelito, broke it in half, and joked, "It’s a culinary workout—lifting weights in tiny dough form!” We laughed—hard. Because bad dates? They can still be great stories.

Tips for Avoiding “Date Overload” (From Someone Who Blundered Big)

  1. Go Simple, Not Spectacle: Sure, grand gestures work in Netflix rom-coms, but in real life, you don’t need Cuban tasting menus or soaring string quartets. Go for places where you can hear each other talk instead of deciphering the wine glossary.

  2. Read the Room—and the Mood: Does your date really need the tasting menu? Maybe they’d vibe more with tacos by the lake or a chill pizza night. Fancy doesn’t mean better.

  3. Embrace Chaos: If things go sideways—and they probably will—lean into it. Bad dates happen, but shared laughs over soggy fries make great memories.

  4. Connection Over Curated Perfection: It’s less about how impressive the plan is and more about how comfortable and happy you both feel. Dates aren’t auditions; they’re collaborations.

Conclusion: From Misadventure to Memoir

That night ended with us heading to a late-night taco spot, laughing in the car over how I tried so hard and failed. It was one of those moments where you realize people (and dates) aren’t perfect, and that’s okay. Ana loved the tacos more than the fancy restaurant, by the way.

Some time later, when she asked me to teach her how to make Cuban coffee, I showed her the process with pride. At least I had my café game down.

Turns out, the real magic wasn’t in the perfect plan, the overpriced plates, or the heavenly setting. It was in letting go of the need for everything to go right and savoring the messy, human moments—in all their pastelito-gone-wrong glory.