It was a Friday. Dean was leaning against a building, and the damp, crusty walls would have given him chills if it weren't for his father's leather jacket.
His eyes roamed the cold city streets, and he ignored the "No Loitering" sign just halfway down the block, but he did take note of the guy hunkered down on the sidewalk a few yards away from him. It was dark out, except for the incessant flicker of neon billboards advertising "The Best Girls in Town!", as well as the sign of the corroding motel where Sam lay fast asleep.
Dean slipped his hand into his pocket and pulled out a half-empty box of cigarettes he jacked from some jerk that pushed a girl with dimples and a cheap push-up bra. He stuck his hand deeper into his pocket and felt his way past some loose change as he looked for the lighter he found on the ground somewhere, but it must have fallen out sometime during the day. Dean smirked. It was probably somewhere in the janitor's closet at school.
Dean was about to close the pack and put it away when the bum slouched against the wall reached out his lanky arm with a Bic lighter in his bony hand.
"Here," the man mumbled through his grungy beard. Dean blinked a couple times, but took the lighter. "Just don't steal it…" the old man grumbled.
Dean looked away, flipped open the pack again, and after a couple clicks lit a cigarette.
"Thanks," Dean said as he gave the man a slight nod and threw the lighter back to him. The homeless guy barely caught it by the tips of his fingers, and only shrugged in reply as he readjusted the grimy blanket that he had wrapped around his narrow shoulders. He pulled out his own box of cigarettes from his torn shirt pocket and emptied the contents into his hand - a penny that flew up at him from the bottom of someone's show as they walked by, and just one cigarette. He gave it a long look before he lit it.
Dean tried not to think about where else that lighter had been as he brought the lit cigarette to his shiny, but chapped lips. He breathed in, then coughed up the smoke and frowned.
"First smoke?" the old man asked as his crummy eyes looked up at Dean. He nodded at the man as he lazily waved the smoke away from his verdant eyes. Dean took another drag and tried to not look like he was about to choke. He stared at the stolen cigarette, then let it fall to the wet concrete beneath his feet before he stomped it out with the heel of his boot. His eyes followed the last bit of smoke as it left with a biting gust of wind - then Dean noticed the old man was watching.
"It's bad for you, anyway," Dean said. He refused to let a homeless man make him feel guilty about a wasted cigarette.
The man scoffed. "Like I ever cared…" he answered. He left the cigarette in his mouth for a second to rub his hands together.
Dean looked down at the man. His eyebrows went up a little as he reached into his pocket again, and his hand returned with the now almost-empty box of cigarettes. Dean gave it to the man along with a few quarters. But the bum didn't say anything, he just squinted as Dean walked off, rounded the corner, and disappeared into the night.