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Want to know what Sam did last summer? Find out in this episode.

The story begins with the introduction of Anna Milton, a young woman institutionalized for visions which sound surprisingly familiar – including a demon named Lilith aimed at breaking sixty-six seals to unleash Lucifer. That night a guard comes to her room but Lilith recognizes the man by sight to be a demon. When the possessed attendant moves towards her she knocks him out by psychically pushing a dresser right into him.

While hustling a pool game at a bar, Sam and Dean are met by Ruby, who tells them about Anna’s escape and how she is a person of great interest to the demons of Hell. They quickly take off on a long drive to the mental hospital, but Dean is none too happy to be following a lead from Ruby – someone Sam has little trouble trusting. When Dean probes Sam about his connection to Ruby we are met with a flashback to Sam’s six months without Dean.

As hinted at in the season premiere, Sam tries to make a deal at the crossroads for Dean’s return. But the drunken Sam meets with a far too confident demon not the least bit interested in Sam’s soul – not when they have Dean right where they want him. Sam kills the demon where he stands, but not before the demon admits he has made his peace with “his lord.”

There is even further evidence to Ruby’s claims at the mental hospital, where they discover Anna had visions of everything from the raising of the dead and the release of Samhain. They next stop at Anna’s parents for more information, only to find them murdered with the crime scene covered in sulfur. However, they do find a clue to Anna’s whereabouts – her father was a pastor and many of her drawings contained etchings of the stain-glass windows. Checking at the local church, the Winchesters are shocked to find not only is Anna there, but she knows both of them very well.

Anna explains she can overhear the conversations of angels, hence why she knows Sam and Dean (who are often the subject of their conversations) so well. And that’s why the demons are after her. Ruby bursts in the room and Anna is immediately afraid. She is able to see, like Dean briefly could, the true appearance of demons. Ruby explains that another powerful demon is right on their trail. Despite Dean’s reluctance, Sam goes to “pull” the demon the moment he enters the room. His psychic power barely causes the tickle. The demon easily tosses Sam down a flight of stairs and then proceeds to gleefully pound into Dean – who is on a first name basis with the demon, named Alastair. Sam saves Dean by stabbing Alastair in the shoulder with the knife while Ruby and Anna make a run for it. Shortly after distracting Alastair both Sam and Dean make their own run – right outside a stained glass window.

Back at a hotel the Winchesters are a little worst for wear. Sam is still pulling glass out of his arm and Dean has a dislocated shoulder. With no choice but to wait for Ruby’s call, Dean continues to probe Sam on his reliance on her. Sam explains, through flashback, that Ruby saved his life. Still locked in drunken abandon six months past, Sam was confronted by Ruby – in another body – and another demon. They took his knife, with Ruby revealing Lilith had cut her loose to redeem herself. But Ruby, not surprisingly, kills the other demon. Sam, however, is not too grateful and seems to have preferred death. He is also disgusted by Ruby’s waitress body. Later, a comatose Jane Doe awakens – with Ruby’s voracious hunger intact. She then tells Sam she took the body without another human’s spirit to please him. They start their physical relationship not soon after, though Sam still has a lot of trouble mastering his psychic ability.

Though he’s not thrilled to hear the intimate details of Sam and Ruby’s relationship, Dean isn’t convinced Ruby can be trusted. Five months ago Sam insisted on attacking Lilith head on and even held Ruby at knife-point when she tried to stop him.

Entering a suburban house Sam sees the same child in the blue dress, but soon discovers the child isn’t possessed – it’s a trap. Ruby comes to his rescue while Sam saves the girl, and later, exorcises his first demon psychically. Just then, the maid – a heavyset African-American woman – demands entry to bring fresh towels, which she hurriedly shoves to Dean and gives Sam her address. It’s Ruby – temporarily possessing the maid in order to warn Sam and Dean of the demons outside.

At a cabin in the woods Dean thanks Ruby for watching over Sam, though he’s a little light on the apology (which he considers “awkward”). Anna receives a vision, with Sam, Dean and Ruby waiting for the impending onslaught of demon. They are instead greeted by Castiel and Uriel – the latter none too happy to the see “the stain” that is Ruby. But Castiel confirms they aren’t here to help Anna. They are here to kill her.

This was a good building episode, overall, but is missing something. It seems this season has plenty of funny episodes, but some of the episodes are just too light on humor and too heavy on plot. Still, I like what this story did with the unresolved issues surrounding Ruby, and I’m especially interested in the character of Anna Milton, who seems far more realistic and intriguing than either Ruby or Bela were last season. Unlike the debut of these characters, Anna seems believable in that blue-collar small-town girl rather than overly spectacular Ruby and Bela, who stood out instead of blending in last season.

How does Dean know Alastair, and how will Kripke and company show Dean’s time in hell without actually showing, y’know, hell? We’ll just have to tune in next Thursday to find out!

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