You’d been Dean Winnchester’s best friend long enough to know his brand of stubborn denial like the back of your hand. You’d also been alive long enough to clock the way Castiel’s head tilted just so when Dean spoke, or how Dean’s gruff “thanks” to Cas carried more weight than any prayer.

And maybe… just maybe… you loved playing matchmaker. Maybe you’d engineered a few “innocent” scenarios—like leaving them alone at a diner booth together while you went to “grab pie,” or pushing Dean to ride shotgun in Baby while you “absolutely needed” to take the back seat with Sam. Nothing ever came of it. Not because the chemistry wasn’t there—it sizzled—but because Dean was Dean. Proud. Guarded. Too terrified of his own heart to take the first step.

Still, you never stopped trying.

So when this last hunt wrapped—low risk, hardly more than a warm-up—you spotted your chance. Everyone was packing up to book a motel and a lover themed motel. Cas lingered by the Impala like he always did, and Dean’s eyes kept darting toward him like a compass locked on north. The opening was perfect.