In this episode we get to see more of Deanmon Winchester developing into a full black eyed monster that Crowley has been working on. He wants Dean to be his right hand henchman collecting souls for hell, but Dean just wants to be left alone and enjoy himself with fast women and cheap beer. Sam is still at the warehouse with the mysterious hunter getting a beat down trying to get the whereabouts of his brother. We now know that the mystery man is Cole, a man on a mission of vengeance towards the Dean who killed his father eleven years ago. 
During that time, Dean was hunting a demon and came across Cole’s father. They struggled and he killed him in front of Cole. He is on a mission to find Dean and kill him. Sam tries to reason with him, that Dean is something he has never seen. He begins to tell him about the ongoing battle with demons, vampires, and monsters. Cole is unfazed; he has seen his share of monsters when was in the military. Sam tells him these are a lot worse. While torturing Sam, Cole gets a phone from his family, and Sam takes the opportunity to slip away and escape.
Meantime, Dean is enjoying an exotic dancer in a strip joint in Killdeer, NC. Dean gets too frisky with the dancer and the bouncer steps in. He fights with the bouncer, but it is no contest. Dean seems to enjoy hurting people way too much. Crowley appears and offers him a job. He refuses, but Crowley tells him that he is going through some sort of addiction towards death. That if he leaves it untreated he will do something he might regret. Crowley wants him to be his soul hunter. To satisfy his lust for death, Dean will be Crowley’s reaper to his client. Dean’s first job is a husband who wants his ex-wife to die and deliver her soul to Crowley for payment. Dean meets with the husband and decides to kill the husband instead for being a cheating loser. Crowley is not happy about this. Never in his experience did a demon disobey him. He doesn’t care and tells Crowley that he will not be his delivery boy. With that being said, Crowley realizes that it is a mistake to try to mold Dean into something he’s been hunting all his life.
While Dean is having demon issues, Sam tracks down a lead to the location of his brother. He needs help, so he calls Castiel. Even though he is not thrilled that Dean is a demon, he reluctantly agrees to help Sam. Anna and Castiel head off to where Sam is at. Still weakened by the failing borrowed grace, he struggles to stay conscious, but fails and crashes the car they are in. Somehow they are able to call a tow truck and get it towed to the next town. The truck owner notices that Castiel is injured and offers them to stay the night in her house. Waking up on a couch, a little girl is sitting next to him, he strikes up a conversation with her and they laugh. Anna notices that and so does the mother of the child. The mother tells Anna that she has good man there. Before correcting her she stops and says nothing. Ready to leave the truck owner’s house, Anna suddenly slips away and ascends to heaven. 
She meets with Metatron and tries to convince him to give back Castiel’s grace. He offers to help her in exchange for total freedom. Castiel finds her and stops her from making a huge mistake. Anna doesn’t understand, but he tells her that he has accepted his fate. She leaves while Castiel stays behind to chat with Metatron. He still offers Castiel his grace, but still refuses and tells him that he‘s very satisfied knowing that he will be in prison for all eternity. Metatron vows to get out and destroy everything. Castiel walks away.
Sam finds Dean with Crowley’s help in exchange for the First Blade. Little did Sam know is that Cole is right behind his trail. Sam confronts Dean to try to bring him home to the bunker. Unfortunately, he is more than willing to kill Sam to in order for him to be left alone, but he decides to just walk away. Cole is waiting for Dean outside the bar to end the man who murdered his father. They fight each other and Dean beats Cole badly. Sam uses the fight to blindside him and put him in handcuffs.
On the drive back to the bunker, Sam tries again to reach the human side of Dean. He tells Dean that he is still a good man. By not killing Cole proves that he still has mercy toward others, Dean disagrees. He said what he did to Cole is a lot worse than offering him mercy, but what he is going to do to Sam is going to be much worse than Cole’s. The next scene shows Cole looking through books about demons. It is not over him, not for a long shot.
Do you think Dean will be good again? How far will Sam go to save his brother? Is Castiel dying? Are Anna and Castiel going to express their feelings toward one another? So many questions, not enough answers.
