Lily Sunder Has Some Regrets is an odd title for a Supernatural episode. It sounds like something I might pick for a big bang fic that I can’t figure out how to title, because it’s unusual and might make people go, huh, I wonder what that one’s about? I sometimes really miss the days of classic rock episode titles. But other than the unusual title, this was a solid episode. I will always prefer the Winchesters onscreen 100% of the time (Jared and Jensen do not appreciate my preference, but this hasn’t deterred me), and I haven’t always been a fan of the angels/heaven storyline in the past, but this episode was less about angels in general and more about the one angel I care about – Cas.
Much as we’ve been witness to the evolution of Sam and Dean’s views on when killing is justified and when it’s not, increasingly falling into the gray areas instead of black and white, we were able to see some growth in Castiel’s views in this episode. I was chilled by his coldness in the flashback scenes to the execution of Lily’s husband and child (though even then Cas was the only angel who flinched when the human in the house cried out). But other than that flinch, Castiel was at that time truly the ‘good little soldier’ that Dean has often been disparagingly called. The events of the present were a sharp contrast to that way of being, a reminder of how far Cas has come – and that, in contrast to what Ishim believed – that change is in large part due to his relationship with the Winchesters.