Left alone to fend for himself in a completely unknown place, surrounded by the tortured souls of the things Dean usually hunts, Dean ends up teaming up with someone new— Benny (Ty Olsson). And when Castiel comes face-to-face with this new dynamic duo in Purgatory, he isn’t happy about it:

“He’s wary of Benny from the get-go, and I think he’s possibly a bit jealous, too, of the friendship or camaraderie that happens between Dean and Benny. Cas doesn’t have a lot of other friends in Purgatory!” Collins pointed out.