Ever since I saw Shania, my heart started performing acrobatics that would put Cirque du Soleil to shame. And her brother, Barry, as adorable as a 6-year-old could be, always trailing along, was just part of the package. There was only one problem – I, Caesar, had the social skills of a particularly timid sloth. Enter Gary, my best friend, more outgoing than a salesman at a networking event, and with enough crazy schemes to fill a sitcom.

Plan 1: The Classic. Flowers and chocolate, I mean, who could resist that? The delivery seemed simple enough: stroll up to Shania, present gifts, and then ask her out. Yet, somehow, in our execution, Barry ended up with a face full of pollen and chocolate smeared all over his SpongeBob shirt. His surprise morphed into a sneeze, firing the flowers back at my face. We’d made an impression alright. Just not the one we’d planned.

Plan 2: Serenade under the stars. We borrowed a guitar, learned to play “All You Need Is Love,” and sneakily placed ourselves under Shania’s window one late evening. However, we failed to account for Barry’s acute bat-like hearing. Just as we hit the first chord, out came Barry, ready for battle, brandishing his toy lightsaber. Gary frightened out of his wits, swung the guitar right into a beehive. Poor Barry. If we weren’t on Shania’s blacklist before, we certainly were now.

Plan 3: Showcase athletic prowess. We decided to demonstrate our soccer skills right when Shania was passing by the field. Barry was supposed to be our star audience member. Everything was going as planned until Gary, inspired by David Beckham, launched a powerful kick that sent the ball flying… straight into Barry’s ice cream. Result? Barry: 0, Ice cream: 1, My chances with Shania: rapidly dwindling.

After every disaster, we’d find ourselves in my basement, nursing our wounded pride (and occasionally, physical wounds). But, the sight of Shania laughing, even if it was at our expense, was enough fuel for the next catastrophe.

The final blow came when Shania confronted us. “Why are you constantly tormenting my little brother?” she demanded, concern etched on her face. There I was, standing in front of the girl I was desperately trying to impress, accused of brother-bullying.

I looked at Gary. He shrugged and mouthed, “Now or never, man.” I took a deep breath and confessed. I told her about our botched attempts to impress her, about the flowers, the serenade, and the soccer showcase. How everything had been for her and how, unfortunately, Barry had been the unintentional victim of our endeavors.

For a moment, Shania was silent. Then, to my utter astonishment, she began to laugh. A soft, melodious laugh that sent my heart doing somersaults. “You guys are the biggest dorks I’ve ever met,” she said, wiping away tears of laughter. “And I can’t believe I’m saying this, but yes, Caesar, I’d love to go out with you.”

“But,” she added, “only on one condition. You both will spend an entire day with Barry, making him feel like the superhero he loves to be.”

We agreed, how could we not? And let me tell you, a day with Barry wasn’t easy. He had the energy of a nuclear reactor and the fearlessness of a lion. We built forts, fought invisible enemies, and even hosted a faux cooking show. In the end, we had an absolute blast. And Shania, she watched us, her laughter ringing out every time Barry made us do something particularly crazy.

I’m not sure when we’ll embark on our next adventure. But one thing’s for certain, if you ever see us coming your way, I’d hold on to your ice cream. You’ve been warned.