Set early in season 2, after No Exit.
"So . . . what? No, you're gonna have to go over that again man." Dean laughed as he tried to keep his green eyes focused on the road ahead.
Sam sat huddled up in the passengers seat of the Impala as if hoping the leather interior would give him a little more precious heat – even with the heater on full blast the car had a strong resemblance to an ice box.
"These people . . ."
"Nut Jobs!"
"DEAN! Quit it!" Sam's angry voice silenced his brother momentarily.
"Sorry, sorry. Please, continue." Dean threw his little brother a teasing wink.
"Anyway these people all became . . . well, stalkers." Sam's face screwed up.
Dean grunted, sounding less than impressed and not letting his concentration leave the icy winding road.
Sam was clearly getting fed up of his sibling's lack of enthusiasm. It wasn't like Sam really wanted to be lost on a back road in the middle of a blizzard either. Sometimes their job really sucked!
Sensing his brother had gotten to the end of his rather short tether Dean picked up the run-down.
"And they all blame Cupid?" He exploded with laughter, which – thanks to the freezing cold air – was quickly turned into a dry cough. Damn weather.
"Yeah, well, the ones that are still alive do." Sam turned to face the window, knowing full well that the mention of death would spark his brother's interest. Sam could almost time how long it would take before Dean wanted more info.
The boys had been put onto the bizarre case thanks to a sketchy phone message from Ellen. She'd heard talk of a series of suspicious deaths in Applewood, Colorado. People seemingly becoming obsessed with their partner and eventually ending their lives. After a quick stop off at the Roadhouse (and an awkward stand off between Jo and Dean) the boys were on the case. Until the mention of Cupid they hadn't been interested but they couldn't let it go. It was certainly a first for them. Dean still couldn't say the word without laughing.
"So is there any kind of lore?" Dean asked as they sat in a roadside cafe, nursing 2 cups of stale coffee.
Sam shook his head.
"No, this isn't our usual gig though. I mean how often do you hear about an Evil matchmaker? It doesn't exactly sound terrifying though does it."
The younger of the two men was now visibly shaking with the cold.
Maybe the Impala had been warm after all. Everywhere seemed freezing at the moment. Sam made a mental note to avoid holidays to Colorado in the future. That was if he ever got a holiday!
By the time the Winchesters left the cafe it was nearing midnight. Now, half an hour later there was complete silence inside the car. Sammy had fallen asleep shortly after sitting down. He had somehow managed to get comfortable and curled up under a blanket. Most likely stolen from a past motel.
As Dean looked across at his lanky sibling he smiled. Or at least he would have, had his face been warm enough to move! Even in the most unpleasant times they were a team. Sam might never know how much his company meant to Dean.
After another moment Dean shook his head. Was he going soft?
To prove otherwise he pushed one of his favourite Blue Oyster Cult cassettes into the tape player. As soon as the music came blasting out of the antique speakers Sam sat up straight. He was none the wiser to Dean's momentary relaxing of emotions.
Finally, a little after 2am, a snow-caked Chevy Impala pulled into the Sacred heart motel parking lot. Two young men protected from the elements by layers of clothing climbed out. Immediately both boys regretted taking Ellen's job as they looked around the sleeping town. This sure wasn't shaping up to be a fun job.