Sorry this took so long, I was pretty stumped.
DCJ. Canonverse. Divergent…. somewhere around season 6/7/8-ish.
Jimmy’s been riding shotgun in his own body long enough to know what’s going on unspoken between Dean and Cas. He knows the look in Dean’s eyes and he knows the churning emotions Castiel is developing aren’t just about the bigger picture of heaven and hell and humanity. There’s not a whole lot he can do about it, though.
That is until after the whole Godstiel fiasco. After he wakes up in the home of a strange woman, completely alone in his own body, he’s not sure what he should do. He finds Amelia and Claire, happy without him and he doesn’t even bother barging in and ruining their lives… again. The only thing left to do, really, is find Dean and figure out what the hell happened to Cas. That’s easier said than done, though, because Castiel isn’t answering and Dean…
Jimmy understands. He knows their baggage, their lingering looks, their longing. He’s lived it, after all. It just doesn’t help that Dean still looks at him like he’s the angel, or that Jimmy finds himself wishing that he could either make it stop or make a move. He’s not sure if whether or not it’s a mistake when they tumble into bed together, desperately wishing things were different.
And then, wouldn’t you know it, Castiel pops back in, a whisp of his former angelic glory, desperate for a safe haven. Heaven isn’t pleased and they’re looking for him. Jimmy says yes once more, and in doing so subjects all three of them to a brand new level of hellish longing.