When an angel in his former battalion cries out for help, Castiel must find out who's responsible and stop them before they come for him.
While there is still no word on the whereabouts of Kelly Kline, Dean and Castiel aren't on the best of terms with one another at the moment. Castiel is sure that he did the right things but Dean isn't so sure due to Billie's foreboding mention of cosmic consequences if the deal was broken – which it was. Rather than stay in the bunker to talk it out, Castiel intends to go and speak with his former brothers in arms. Sam insists that they go with him and Dean reluctantly agrees. After they arrive, Castiel tells the Winchesters that he needs to meet with the angels, Isham and Mirabelle, alone as Isham detests humans. The boys agree but that only holds up for a total of five minutes before Dean goes barging in with Sam in tow. Castiel and Isham explain that Benjamin was skilled fighter and could not have easily been killed. Mirabelle leaves to make sure they weren't followed but is killed in the alley behind the restaurant by a red headed woman with an eye patch. The other leave and find Mirabelle dead when suddenly Isham is attacked and wounded by the woman and only manages to survive with Castiel's help. Sam and Dean join the fight but the woman mentions that she has no fight against humans and manages to escape. Later on at Isham's safe house, Castiel mentions how he recognized the woman as Lily Sunder. Castiel and his team were sent to her family's home in 1901 to destroy her child - a nephilim child born from a human and an angel. Their Somehow, more than a hundred years later, Lily Sunder is alive and is taking revenge on those responsible for her daughter's murder.
Evenly paced and giving us more angel backstory, Lily Sunder Has Some Regrets was a solid episode from Supernatural with some faults. Hearkening back to the Castiel of old in season four, Isham, Mirabelle, and Benjamin reminded us of the soldier that Castiel used to be several years ago. It's all too easy to forget that Castiel was the one that pulled Dean from perdition and the one that threatened to throw him back. The result of Lily Sunder Has Some Regrets was that it further illustrated the character arc that Castiel has had over the years and shows just how much the character has grown. Where Lily Sunder Has Some Regrets definitely struggled was in the flashbacks and how on the nose the dialogue was. The show had limited time to tell the story but for how important the flashback was, it seemed like an afterthought as the entire relationship between Isham and Lily was revealed and solved within three lines. Had there been more flashbacks that focused on Isham's obsession with Lily and how she ultimately rejected him there would have been a much deeper connection to the characters and what Lily experienced and what drove Isham to his actions.
Another point that felt like a missed opportunity was the idea/morality behind killing a nephilim child. Neither Sam nor Dean really took a stance on this when it was brought up by Castiel when he asked if he deserved punishment. It's not the suggestion that they should have either way but it is a question worth asking. Was it right for them to kill a child knowing what it could become but not being certain if that would actually happen? It was a good point when Castiel said that he would not have questioned it before but he certainly would now. Do Sam and Dean feel the same way? It felt like a great character moment that was missed in the excitement.
Overall, Lily Sunder Has Some Regrets was a good episode that gave us more Castiel backstory while still bringing something new to the table. One question though: if the angels all lost their wings because of Castiel, why do they still have them when they die? Hopefully Supernatural follows up with another good episode in next week's Regarding Dean.