Dean hates Monopoly. Correction: Dean used to hate monopoly. Watching Castiel turn purple because he lost the spot he’d been aiming for the entire game to one manipulating Sam is the best thing in the world. Almost better than pie.
Castiel is boiling over like a kettle, and he still refuses to stop playing. Sam is being a bitch – when isn’t he? – and took that spot not only to have an unfair advantage (it’s that really expensive one people hardly land on but when they do they never survive) but to rub it in the angel’s face.
And really, Dean is on Castiel’s side for this one. The angel mentioned it once, maybe, and Sam stored the statement away like the criminal lawyer he should have been, and used it against the poor guy. This is his first time playing. Why in the hell would Castiel ever want to play again after this?
Dean pats Castiel’s shoulder because it seems like the right thing to do. Castiel’s fake unaffected expression disappears at that, and his eyes soften like Dean’s only seen a few times. The angel looks like he’s begging to be put out of his misery. It’s just a goddamn game; Dean shouldn’t be feeling so bad.
Sam sighs when he notices the pathetic expression on Castiel’s face. “I call break. I’m going to find something to eat.”
They’ve been playing for three hours already. Dean can agree with that.
Digging through his wallet for a credit card, Dean hands it to Sam. “Get me some grub, too. I’ll stay here and plot against you with Cas.” He nudges Castiel with his shoulder, and Castiel slumps against the chair, looking about ready to cry.
“I’ll…be back in a bit.” Sam says carefully low. Maybe hearing Sam’s voice will set off Castiel’s angel-rampage-mode, or worse, his tears.
Dean leans against Castiel to get his attention when Sam is on the other side of the door. “Are you really this upset over a game?”
“He knew of my intention, and yet he still bought it.” Castiel shifts away from Dean.
And is that sniffling? That’s not something Dean has ever been good with handling.
“Well, that’s part of the game, Cas. And everyone always tries to get the really expensive places.” Dean winces when Castiel’s teary eyes dart up to him.
“How can I win now?” Castiel asks, crossing his arms. “The best property has been taken.”
“It’s not always about price. You have a ton more places spread across the board. It’s like Cas land-mind world. He’s going to be in trouble once you guys start buying houses and hotels. Trust me, man.” Dean reaches for Castiel’s shoulder again, rubbing invisible patterns against his coat.
“I trust you with my life, Dean,” Castiel admits, “but not with this game.”
Dean hates Monopoly – again.
Dean secretly cheers on Sam when he gets back, not bothering to console Castiel when he looks defeated on each roll of the die. As Dean correctly guessed, Castiel wins because Sam doesn’t have enough safe zones on the board.
Castiel asks to play again, but Dean drinks until he passes out to not have to deal with watching them.