Sam and Dean are trying to hustle a guy in a bar at a game of pool when Ruby shows up. She tells them about Anna and that the demons are on a mad chase to find her and keep her alive. She tells Sam and Dean that they may want to find her and see why she is so important. Dean is not happy and tells Sam that he is treating her like she is family now. Sam tells Dean that Ruby saved him and if he wants to trade stories, Dean can go first.
Sam flashes back to 6 months earlier when he summons the crossroads demon. Man, am I glad that they didn’t go there with that story line. He called Sam his “co-worker”, that is not a good sign. Of course, Sam wants him to free Dean, which is impossible for him to do. Sam tells him to trade for Dean. The demon tells Sam that they have everything exactly the way they want it.
They arrive at the hospital Anna escaped from and talked to her doctor. She is convinced that she is schizophrenic. Sam and Dean go to talk to her parents and find them dead. They see a picture of Anna at church and remember the window from one of her drawings. They believe she is there, hiding. They get to the church and find Anna hiding. When they tell her who they are, she has heard of them. She tells them that the angels talk about Dean and that they believe that he will save them all. And that they don’t like Sam. She tells them that she can hear angels and it just so happened that she started hearing them the day Dean was pulled out of Hell. The first thing she heard was “Dean Winchester is saved.” Ruby shows up and says there is a demon after them. They hide Anna and Sam tries to exorcise the demon, but cannot. The demon knows Dean; it was someone he knew in Hell. Ruby manages to get Anna out as Sam and Dean get their butts kicked. Sam stabs the demon with the knife, but it does nothing. They jump out the window to get away, but leave the knife behind.
Dean is really nervous why Sam trusts Ruby so much. Sam finally tells him what happened while Dean was gone. Sam was jumped by a demon and Ruby (different body) just happened to be the other one. She played along that she was going to kill Sam and killed a demon instead. Sam kicks Ruby out of the car after they talk and he tells her to let the body go. So, she jumps to a body of a girl who is about to die. She shows up and tells Sam she can give him Lillith. She teaches him how to use his powers. Then, she comes onto him. Now I know why Sam likes her so much.
Dean is a little freaked out that Sam did the deed with her. He goes on to tell Dean that Lillith showed up in town and Ruby begged him not to go after her. He did anyway. It ended up being a trap, but Ruby showed up to save him. Sam ends up saving her by killing the demon who had her pinned up against the wall. While they are talking, “Ruby” shows up in the form of a housekeeping lady to tell them to leave. She is at a cabin with Anna. They arrive and Dean apologizes to Ruby, in a round about way. Anna is still worries about her parents, and they tell her that her parents are dead. She is upset and stops to say, “they are coming.” But the they are the Castile and Uriel. They say that they are there for Anna and she has to die. And then the thing that I dread the most………. TO BE CONTINUED! NOOOOO!