My First Date With Her

I had planned it out a dozen different ways. A walk in the park? Too cliché. Dinner and a movie? Too safe. Karaoke? Too bold. After hours of overthinking and two calls to my best friend, I finally settled on a little rooftop café downtown that I’d seen on Instagram. It looked like the kind of place where first dates turned into long-term love stories. Or so I hoped.

Her name was Riya. We’d met at a mutual friend’s birthday party, where she laughed at my lame joke about the cake being "a lie." She was effortlessly funny, charming in the way she talked with her hands, and beautiful—like, stop-time beautiful. When I asked her out, I half-expected her to say she was busy forever. But she smiled and said, “Sure, let’s see what you’ve got.”

And now, here I was, ten minutes early, nervously adjusting my shirt collar and rehearsing lines in my head like I was auditioning for a rom-com. I ordered a coffee just to have something to hold. My palms were sweating, but the cup made me look occupied. I kept checking my phone, pretending not to care, pretending I wasn’t on the verge of a heart attack.

She arrived exactly on time, wearing a simple blue dress that somehow made her look like she belonged on that rooftop more than anyone else. She smiled, waved, and all of a sudden, the background noise faded.

"Hey," she said, pulling me into a friendly hug. "You look nervous."

I laughed, because it was true. “Only a little. Okay, a lot.”

The waiter led us to a table near the edge of the rooftop, city lights twinkling like we were sitting in the middle of a postcard. The sky was kind enough to stay clear, with just enough breeze to feel cinematic. I mentally high-fived myself for the choice.

We talked. About everything and nothing. Her love for Korean dramas, my secret obsession with chess, her job at a publishing house, my ongoing attempt to write a short story I hadn’t let anyone read. The words flowed easier than I’d feared. She had this way of making you feel like your words mattered, even when they were awkward or silly.

Then I knocked over my drink.

One second, I was explaining why pineapple on pizza is underrated, and the next, my iced tea was a puddle spreading toward her side of the table. I jumped up, knocking my chair over in the process.

“Oh God, I’m so sorry!”

She stared at the mess, then at me—and burst out laughing.

“Relax,” she said, grabbing a handful of napkins and helping me clean up. “It’s just tea. Unless you were going to propose with that glass?”

I smiled sheepishly, and she winked. “Now I’ll always remember our first date as the one where you tried to drown me.”

After the cleanup, we ordered dessert—two slices of cheesecake that arrived with little sparkler candles in them. The waiter winked and said it was “for good luck.”

“Think we’ll need it?” I asked.

She looked at me thoughtfully, then leaned in just a bit. “Maybe not. I think you’re doing okay.”

The night went on. The city got quieter, and the stars finally showed up, like they were late to the party. When it was time to leave, I walked her to her ride, not really wanting the night to end.

“I had fun,” she said, tucking her hair behind her ear.

“Even after the iced tea incident?”

“Especially after that,” she grinned. “It was real.”

There was a pause. That nervous kind of pause where you don’t know if you’re supposed to lean in or step back.

So I said, “Would you want to do this again sometime?”

She nodded. “I was hoping you’d ask.”

Her ride pulled up. She got in, rolled down the window, and said, “Next time, though, let’s skip the drink shower.”

I laughed and waved as the car pulled away. As I stood there in the soft glow of the streetlight, I realized something: it hadn’t been perfect. But maybe that’s what made it great.

It wasn’t a movie. It was better. It was real.

And I couldn’t wait for the sequel.