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It was the night after a particularly peculiar case; a killer goldfish had been terrorizing a family in Cannon Beach, Oregan. Dean had gone out for drinks, not bothering to shower the stench of rotting fish off him, while Sam stayed back at the motel. Cas had dipped shortly after they got back for some ‘heavenly business’, which sounded like a second-hand angel circle jerk to Dean. Sam mostly stayed back to pack their things back into a somewhat decluttered pile by the door for the next day, but also to get some peace and quiet so he could watch random flicks on the shitty cable tv. Gone in the Wind, Jurassic Park, Mean Girls? It wasn’t until around 2:40 am that Dean fiddled with the motel door lock and stumbled through the door, clearly hammered to the 9s.
“Looks like you had a good night,” Sam said, giving him a once over with a smirk.
Dean didn’t even bother to look at Sammy, huffed, and simply flipped him off for good measure. He started to tear off his coat but struggled to do so. Sam stood up from his bed and attempted to help him, but was shrugged off by his brother. In Dean’s scuffle, he managed to trip over his feet and fall on the ground.
“See, got it off,” Dean replied, holding the jacket above him. Sam reached his hand out and Dean took it and teetered up.
“Are you alright?” Sam asked, knowing full-well this wasn’t the normal drunk Dean he knew. Too grumpy.
“Fuckin’ peachy, Sammy,”
“Okay well, do you wanna watch the rest of this with me?” Sam asked, nodding to the tv, which was currently showing a guy with a mohawk and facial piercings talking about pissing on the Pope.
“Eh, why not,” Dean replied, flopping down on his respective bed. Sam took off his brother’s shoes and belt, throwing them on the table by the covered window. Sam then hopped into bed, turning up the volume, and resting his head on a pillow. Sam suddenly heard whimpering coming from his right, which announced itself with a loud sob. Dean was crying, hugging a pillow, and watching the (previously outcasted) guy get the beautiful girl on screen.
“Hey hey, Dean, what’s up?” Sam purred as he paused the show, and padded over to where the older Winchester wept. Dean smothered his head in the pillow, avoiding any eye contact with his younger brother. He felt the bed lower as a presence sat beside him.
“No, it’s nothin,” Dean remarked, trying to shake off his brother’s attempts at comforting him.
“Dean, it’s obviously not,” Sam said, huffing. As he got no response in return, he decided to try to figure out with a game of ‘let’s-guess-what-the-fucks-going-on-in-dean’s-head-today’.
“Does it have to do with the case?” Dean shook his head, face still hidden in the pillow, like a young child hiding from the boogeyman.
“Was it the bar? Did something happen?”
“It’s more like, what didn’t happen,”
“Could you not pick up a single girl?” Sam said, slightly smirking. He’d absolutely cackle if Dean were crying over losing his ‘charm’. Dean lifted up his head from out of the pillow. “Look it’s not about some stupid girl. I just- I had plans with someone and they never showed, okay,”
Sam took this time to think. Was Dean ‘The Meat Man’ Winchester crying over being stood up? Is this why he’s so pissed drunk?
“Who was it? Do I know them?” Sam asked, trying to find some answer in Dean’s solemn green orbs.
“Dean, come on. You can tell me. It’s not like I’m going to talk to her behind your back-”
“It’s Cas,” Dean blurted out, obviously annoyed by Sam’s belligerent nagging. “I asked Cas out for drinks after the case, he said he’d come after his business upstairs. He never fuckin showed. I thought maybe he felt the same way but ya know, apparently not,” Dean slurred, wiping a hand over his tear stricken face.
“The same way? About what?” Sam questioned, a confused expression on his face. ‘Jesus, is he really that fuckin clueless?’ Dean thought as he sighed.
“I love him, okay Sammy? For fuckin years, ever since purgatory I just- I thought maybe now, he might feel the same way,”
Dean threw his head back into the pillow, wallowing in self-pity.
Sam suddenly bursted out laughing, full-on belly chuckle. “Jesus, what now? C’mon I know I said no chick flick moments but I just spilled out my guts to you. Now you're just being a dick about it,” Dean blurted out, clearly frustrated by his younger brother’s childish antics.
“Dean, you poor idiot,” Sam said, trying to gasp for air after his laugh attack. “What?” Dean replied, now being the confused one.
“Have you seen the way Cas looks at you? Those puppy dog eyes with that doe-eyed stare? He clearly loves you, man. One time he actually told me that he was going to try to ask you on a date, but then we went on this case. He swore me to secrecy,” Sam explained, clearly amused by the new expression upon his brother’s puffy face. Hope (and a little bit of kamikaze eyes to even it out).
“You’re serious? Cuz’ if you’re kidding with me, I’m gonna lock you in the trunk and make you stay there til’ we get home. I’m not fuckin around,”
“No Dean, I’m being serious,” Sam replied, in a serious tone, knowing Dean was being perniciously deadass.
“Alright, well then, what the hell do I do?”
“In normal circumstances, I’d tell you to sleep off the alcohol and wait till morning. But I mean, this is nowhere near normal. We're talking about an angel, man. I’d say go for it.” Sam cheered, putting an encouraging hand on his brother’s shoulder.
“But how, the guy never showed up the first time, whats the chances he’ll come when I actually need to talk?” Dean muttered, sitting up to put his belt on.
“Uhm, I dunno, maybe pray to him?” This whole ramble was interrupted by a door opening and a trenchcoated figure with chestnut brown hair and sparkling blue eyes walking through it.
“Well, I’d say this is my cue to leave,” Sam said, grabbing his coat before murmuring out, “I’m gonna take a walk,” sticking a thumbs up in Dean’s direction and disappearing through the motel door.
Cas tilts his head in clear confusion and looks to Dean for an answer.
“Cas, sit down. There's somethin I gotta tell ya, and you’re probably gonna need a whole liquor store afterward.” Dean stammered, closing the motel door, and turning off the tv.