Gosh....this idea is so retro, but I need a crossover where Dean Winchester ends up in Faerun (maybe instead of Purgatory or something) and he spends the entirety of the first two acts having to be held back from knifing Astarion and bonding with Wyll and comparing Gale to his "nerdy little brother" and looking for his angel. And everyone just assumes he's looking for his partner and they point him towards the Nightsong (he thinks Cas' picked up a new moniker) and trying to avoid the gay panic Astarion's sending him into (all while denying to himself that he and Cas are more than Just Friends (TM)).

Then he goes down to the Gauntlet of Shar and there's some body double angst and he meets Dame Aylin. He realizes that she's not *his* angel, but is *someone's* angel....and *oh.* all the denials about Cas suddenly seem different.

(then maybe Cas gets rescued from the pods with Zevlor or he's whisked off with the Duke to be turned into a puppet for the Absolute and Dean has to keep adventuring to get him back.)