The Premise: Everyone is in high school. Cas and Dean are dating, or have an epic bromance like usual, and have gotten into a fight. Sam takes advantage of this.
"Are you sure this will be successful?" Cas asks, looking so much like a wounded puppy dog that Sam wonders how on Earth such an angel ever got with Dean Winchester of all people.
"Just… Just trust me, Cas. He'll forgive you, I promise." Sam gives Cas a reassuring pat on the back and gives him the winning Winchester smile that never failed to win over many a heart.
"I do not know this Peter Gabriel person, though. He was not one of the artists Dean said were…" Castiel searches through his memory for the term, "Gods of rock."
"It's okay, he'll know it." Sam smiles reassuringly, and Castiel misses the mischievous glint in his eyes. "Now just press play and lift the boombox over your head."
Sam runs to the side of the house as Cas complies with his orders, and smirks as the boy stands there, boombox lifted over his head, in his signature trenchcoat.
"Your Eyes" starts playing loudly, loud enough to wake Dean from sleep, but not allowed to drown out the "What the fuck!" Dean lets out as he is woken up.
Sam watches the scene unfold, a lost Cas unknowingly impersonating Say Anything's John Cusack, Dean looking out the window like the swearing damsel he was. Sam knows he's in the clear when Dean bursts out into laughter and all is forgiven. It was a petty fight in the first place, nothing Cas' big blue eyes couldn't fix. Dean had a weakness for big puppy eyes.
Sam just couldn't resist.
The trenchcoat was asking for it.