My Most Awkward First Date Ever

First dates are supposed to be magical, right? You get dressed up, put on your best smile, and hope sparks fly. Mine, however, turned into the kind of night you only talk about when you’re trying to make people laugh—or when enough time has passed for you to stop cringing at the memory.

I remember getting ready like it was a job interview. I stood in front of the mirror rehearsing things to say, testing out different smiles, even practicing how I would casually laugh at her jokes. I told myself over and over again, “Just be cool. Don’t overthink it.” But I am an overthinker by nature, so I was doomed from the start.

We had agreed to meet at this small café downtown, the kind of place with dim lighting, indie music in the background, and baristas who look like they’ve read more novels than you’ll ever own. She walked in, looking way better than I expected, and instantly my confidence took a nosedive. I suddenly became hyper-aware of everything: my posture, my handshake, even how loudly I was breathing.

The first ten minutes weren’t too bad. We talked about school, hobbies, and favorite movies. I was sweating like I’d just run a marathon, but somehow, I was holding it together. Then the food arrived, and that’s when the universe decided to have some fun at my expense.

Out of all the things on the menu, why on earth did I order spaghetti? I don’t even like spaghetti that much, but in that moment, I panicked and just picked something random. As soon as the plate landed on the table, I knew I had made a terrible mistake. Trying to look smooth, I twirled the pasta around my fork, only for a rogue noodle to snap off and catapult sauce across my shirt. Bright red. Dead center. It looked like a crime scene.

I tried to laugh it off and made some dumb comment like, “Guess I’m saving some for later,” but inside I was praying for the floor to open up and swallow me whole. She gave me a polite giggle, the kind that says, “I don’t want to make you feel worse, but wow, this is awkward.”

Desperate to recover, I decided humor was the way out. So I told a joke. I don’t even remember what it was now, but I do remember it being painfully unfunny. She stared at me, clearly confused, and I panicked again. Instead of dropping it, I made the ultimate rookie mistake—I started explaining the joke. Nothing kills a moment faster than dissecting something that wasn’t funny in the first place. By the time I finished rambling, she gave me the tightest, most forced smile I’ve ever seen.

At that point, the night was already a disaster, but the grand finale was still waiting. When the check arrived, I confidently reached into my bag, only to pull out the wrong wallet. Instead of my actual wallet, I had grabbed my old one from high school. Inside were three crumpled bills, an expired student ID, and a smoothie loyalty card with two punches left. My heart sank.

I tried to play it cool, but my face gave me away. She realized what had happened and, to my eternal shame, she ended up paying for the meal. I offered to pay her back, of course, but the damage was done. The first date ended with her footing the bill, while I sat there feeling like the world’s biggest clown.

Needless to say, there was no second date. For weeks after, I couldn’t even walk past that café without feeling embarrassed. Every detail replayed in my mind on a loop: the sauce stain, the bad joke, the empty wallet. At night, I’d cringe so hard I’d bury my face in the pillow just thinking about it.

But with time, I’ve learned to laugh about it. That night taught me a couple of important lessons. First, never order spaghetti on a first date. Second, always double-check your wallet before leaving the house. And maybe most importantly, sometimes the worst experiences make the best stories.

Even now, when I tell people about my most awkward first date, they always end up laughing harder than I do. And honestly, that’s fine with me. If nothing else, at least my disaster of an evening turned into a memory worth sharing. It may not have been romantic, but it sure was unforgettable.