A short story for mature readers.

“A crusty, middle-aged loser is afforded a second chance at love, with tragi-comic (and self-actualized) consequences.”

Which window was hers’? The left or the right?
He threw the rock in the air & caught it: once, then twice, then over again; thinking it over, the thud against his hand cracking through the silent night air. He had seen this done a million times in the movies before, and he didn’t recall one single time that it didn’t work. He was going to give it a shot.
Any second now.
Thud, thud, thud…
Em would love it, he was sure. The gesture. Classically-romantic. Chivalrous. Well, not really. There was no way to climb up to her window except if he was Spider-Man; or if he lowered himself down from the roof, which he could see himself getting to via a Mouse Trap-esque Rube Goldberg setup that nature & suburbia had blended together over generations, like that tree in the neighbor’s front lawn with the long-reaching branch, that he could use to get to the neighbor’s roof, and then a hop over. He didn’t care about the neighbor so much. He was a goof.
No, forget it. Forget it! It was ridiculous! He expected himself to what, clip the carabiner that held his water bottle to his bicycle out-front to the laundry line? Tyrolene-traverse himself across, like he was James Bond? That would be pretty cool. But what was more likely to happen was him falling pathetically from the tree – after only getting maybe halfway up, barely passed the stump – and break something. His ankle, perhaps. But that was all hypothetical. Right now, he was trying to get laid, in the most dignified way possible.
Left or right window?
Crap… he dropped the rock. It tumbled a few times away from him in the grass before coming to a halt. Suddenly, things didn’t seem so quiet anymore. He was wasting time… pick one! Before somebody calls the cops. Some nosy, restless goof up at two AM on a Saturday morning! He picked the rock up and noticed it was damp now from the dew on the knoll. He looked back up at the windows, and threw the rock at the left one.
Left. He was sure that was the one. Too late now, as it tapped violently against the dormer, ricocheting off the glass & coming back at him on the ground by his feet. Why not pick it up and try again? OK, he will. He picked the same rock up and threw it back against the same window.
It sailed through the glass making a perfect hole, like a bullet. And as a gunshot would, the sound rang long & far, and it was a matter of moments before every dog in a two-block radius was getting in on the clamor. Crap! That wasn’t supposed to happen! That never happened in the movies!
What should he do? Should he stay? Should he go? Like that song… get the damn song out of your head right now, man! This is serious stuff! A light turned on through the left window – what was left of it – as a man’s silhouette approached & lifted the busted shutter. “Are you fucking nuts? Who’s out there? There’s no use hiding: I can see you from behind the shed!”
“…Hi Derrick!”
“How do you know my name? Do I have to come down there and kick your ass?”
“It’s George!”
“George? As in, Emma’s George?”
“Yes! I’m sorry I broke your window!”
“She’s not even here tonight, dude! You’re just lucky our parents are out too! What the fuck are you doing?”
“…I was trying to be romantic.”
“What?”
“I was trying to be romantic!”
“Did you think the rock was just going to bounce off like it was ‘Romeo & Juliet’? Did you even see the size of this rock?”
“I was sure it was a small one!”
“A small one? Look!” Derrick bent down and picked the rock up, holding it high up: “This thing is fucking enormous!”
“Well, it didn’t seem that big a second ago!”
“It’s huge!”
“I’ve been out here a while, OK?”
“What the Hell is going on out here?” It was the next-door goof patrol, sticking almost his entire upper body out his upstairs bedroom window, “Hey Clear-mont, do I need to be calling the cops or what?”
“No, it’s good Bob, thanks! I’m taking care of it.”
“Well take care of it faster, cause some of us are trying to sleep!”
“George, go away. I’ll call you tomorrow.” Derrick closed the shutter and the impact against the sill broke some more glass from the frame. You could hear the shards rolling down the eave, with some making it to the edge, pitter-pattering on the concrete below like rainfall. George was pretty happy with how the whole experience went, really. It could have been way worse, like, if he didn’t get along with Em’s brother. Or if Em really was home, and he got the window right after all, but it broke her glass and scared her. And then he would be explaining to her why he thought it was romantic to break her bedroom window at two o’clock in the morning.
He walked around the front of the house only to find that his bike was missing. Where did it go? Wasn’t this where he left it? How long had he been standing there?