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|At a hospital, a woman, Anna Milton, is staring off into space. The doctor asks if she knows where she is and if she remembers what she did. Anna says she was trying to warn everyone but realizes it was stupid. The doctor pursues the matter and Anna insists it's all true: the Apocalypse is coming. Anna explains that Lilith is trying to free Lucifer but then seems to hear something. Anna explains there are 600 seals but Lilith only has to break 66, so the angels are losing and they're all going to die.Later, an orderly brings Anna her meds but she wonders what happened to his face. His eyes turn black and the orderly comes in. Anna concentrates and shoves a case into him, slamming him into the wall. She slips out the door and into the night.
A seemingly drunken Sam is playing pool for money and losing. He turns it around, but notices Ruby at the bar and leaves the money to go talk to her. Dean is less than thrilled for her to be there. She tips them off that Anna has escaped and the demons are looking for her… with orders to take her along. Dean isn't interested in anything from Ruby, but Sam decides to pursue the matter. As they make the three-day drive to the hospital, Dean wonders what Sam has been doing getting involved with a demon. Sam doesn't want to discuss it and brings up Dean's reluctance to talk about his time in Hell. Dean backs off, but Sam remembers…
Six Months Earlier
Sam summons a crossroads demon and it insists on seeing the demon-killing knife first. It refuses to bargain for Dean's life and Sam stabs it through the hand. Sam demands it take him for Dean but the demon says they have Dean right where they want him.
Sam and Dean arrive at the hospital and talk to Anna's doctor, who says the orderly doesn't remember anything that happened. The brothers are skeptical and the doctor explains that Anna simply flipped one day, overtaken by delusions that she saw demons everywhere. Among Anna's papers are references to "Raising the Witnesses" and the freeing of Samhain.The guys go to see Anna's parents and find them dead, their throats slit. Dean recognizes some of Anna's sketches as the window from her church. They go to the church and find Anna hiding there. They try to talk to her and she knows who they are. She's heard the angels talk about them and knows that some of them think Dean can save them, and don't like Dean at all. She explains that she can overhear angels in her head. The voices started the day Dean was released from Hell. They figure the demons want her so they can listen in on their enemies. As Anna asks if her parents are okay, Ruby comes in and Anna retreats in terror. She warns a big-time demon is coming but Dean thinks she's lying. Ruby says the demon follow them, and they see a statue of Jesus start bleeding. Ruby says the demon is there and Dean examines the statue while Sam gets Anna into a nearby room for safety. Ruby says that Sam has no choice but to use his powers. The demon, Alastair, bursts in and Sam tries to stop it but it shrugs off his powers and tosses Sam down the stairs. Dean attacks it with the knife and the demon asks Dean if he recognizes him, saying they were close in Hell. Ruby gets Anna out while Dean finally recognizes Alastair. Sam tries to stab Alastair but doesn't deliver a killing blow. The brothers realize that Ruby has left with Anna and leap out a window to make their escape, leaving the knife behind.
Dean and Sam get to their motel to tend to their wounds and Sam wonders who the demon was. Dean doesn't answer and wonders if Ruby can be trusted. Sam insists they can and figures Ruby hasn't called because Alastair is watching them. Sam says they have to lay low and Dean wonders why Sam trusts her so much. He says that Ruby saved his life.
Six Months Earlier
A drunken Sam returns to his hotel room and two demons attack him. One of them is Ruby, in a new body. She takes the knife and explains that Lilith gave her one last chance in return for killing Sam. Sam tells her to do it and Ruby stabs her fellow demon instead. She tells him they have to go and they hit the road. Ruby wants to get something to eat but Sam isn't interested. Ruby explains she's a fugitive on Sam's behalf and Dean wants to know if she can help him save Dean. She admits she doesn't know anything powerful enough. He stops the car and orders her out. He asks her whose body she's wearing and she admits it belongs to a secretary. He tells her to leave it or he'll send her back to Hell.In a hospital, a young Jane Doe is dying. The doctors disconnect her from life support, but she suddenly revives and asks for food. Sam is at a new place when Ruby arrives in her new (present day) body. She has a medical record proving her body was brain-dead, and she says she has something else for him. She offers him Lilith and he's eager to use his powers. However, she explains that Lilith is up to something big and they need to take the time to get it right this time. Ruby tells him to sober up and she'll teach him everything she knows. He practices on a captive demon but fails, and Lilith kills it with the knife. Ruby assures him he'll get over losing Dean but Sam refuses to talk about it. She reminds him she used to be human and remembers what it means to lose someone. She apologizes and then kisses him. He shoves her away, but she continues to come on to him and he finally gives in.
Dean is less than thrilled to hear about Sam's sexual escapades. Sam continues with ho he found signs indicating Lilith was in town…
Five Months Earlier
Ruby warns that they're not ready to confront Lilith. When Sam insists on going, Ruby realizes he's on a suicide run but Sam shoves her aside and goes anyway. Sam goes to the house and finds a young girl at a table. The girl begs him to go home and two demons attack Sam. They say Lilith couldn't make it and knock the knife away. However, Ruby arrives and attacks the demons, and tells Sam to get the girl to safety. She kills one but the remaining demon overpowers her. Sam returns and uses his power, successfully forcing the demon out of its host body and sending it back to Hell.
Sam says that he couldn't have made it without Ruby. They're interrupted when a maid arrives with clean towels. She gives an address to Sam, who realizes she's Ruby temporarily in a new body. They sneak out the back and go to the address, where Ruby has Anna. Dean is forced to reconsider Ruby and admits he owes her for Sam. Anna wants to call her parents and Sam finally tells her the truth. She starts sobbing but then says that they're coming. They retreat to a backroom and Ruby realizes that they've lost the knife. There's a knock on the door and then it bursts open… and Castiel and Uriel enter. They're there for Anna and Castiel explains she has to die.
(to be continued)