This is the first half of a two-parter, so I'm going to leave you hanging, but it's Kripke's fault, not mine. Here we go. Anna Milton is in a psychiatric facility, because she claims to hear angels and has been warning mankind about the impending apocalypse, which on this show means she's perfectly sane and one of the few guest stars who plays a character more intelligent than a turkey. She can see demons' true faces, too, so when her orderly's eyes go all black, she uses telekinesis (which she also can do -- just go with it; she has pretty red hair), to knock him out and make her escape.
Meanwhile, Sam is pretending to be drunk, but he's really just a pool shark. Heh. Just when Sam is about to make a killing, Ruby shows up at the pub where he's playing, and ruins his game. She tells the boys about Anna. Sam is receptive. Dean is not. Sam convinces Dean. You know the drill. On the road, Dean wants to know why Sam trusts Ruby. Sam pretty much plays I'm Not Tellin' Na Na Na Na Na Na, in retaliation for Dean not telling him about Hell, but he flashes back to his dark days after Dean's death -- including his botched attempt to make a deal with a (male!) crossroads demon.
At the psychiatric facility, Sam and Dean learn Anna Milton was a normal, happy well-adjusted journalism major until a couple of months ago. Her official diagnosis is schizophrenia, but when our intrepid heroes learn her "delusions" include thinking demons are everywhere, and that the Devil is about to rise up and take over the world, and then see Anna's sketchbook, which includes writing like, "Raising of the Witnesses" and "Samhain the next seal is broken," they check themselves in, too, for a little R&R. Or maybe they just realize she's not crazy. They investigate Anna's house and find her parents dead, and traces of sulfur. On the Milton mantle are family pictures. One was taken in front of their church where her Daddy was a deacon. It has a stained glass window that looks just like one in Anna's sketchbook. They find Anna at the church, and it seems she got her powers on September 18, 2008 -- the same day Castiel gripped Dean tight and raised him from perdition. Ruby finds Sam, Dean and Anna at the church. Anna can see Ruby's true face and freaks. Dean doesn't trust Ruby's warning that there's a demon on their tails, but then a statue of the Blessed Virgin Mary starts crying tears of blood, and he reconsiders, which I can see. However, it's too late...
The demon who finds them is a powerful critter named Alastair, who has a history with Dean -- in Hell. Sam can't exorcise him, and the Knife That Can Kill Anything And Actually Does can't kill him. Ruby secrets Anna away, while the Winchesters and Alastair fight. When Sam loses the knife to (well, in) Alastair, it's clear the Winchesters can't win. They take a dive out the church window, and retire to their motel room, to lick their wounds (well, actually, Sam sews up his own, and pops Dean's shoulder back into its socket). Dean worries for Anna -- certain that Ruby will turn her over to the demon horde seeking her out for angel intel. Sam knows Ruby won't let them down, and finally, Dean convinces Sam that he's got some 'splainin' to do, if he wants Dean to trust Ruby.
Sam explains how Ruby saved his life over the summer -- once from a Lilith-ordered hit, and once from his own foolish kamikaze mission. And he explains how Ruby got herself the body of a girl who was on life-support, whose spirit had already exited the premises, thus shutting down the fangirls' cries of "RAPE" (and replacing them with complaints of "NECROPHILIA"). He explains how Ruby taught him to use his Pimp Hand of Ipecac on demons. And he explains how HE AND RUBY HAD SEX! Not "that" they had sex -- how they had sex. Dean yells, "TMI!" I yell, "I knew it!" And my word, the Padalecki's shoulders ought to be bronzed. Ahem. Anyhow, Ruby appears briefly as motel housekeeping to tell the boys they're surrounded by demons and where they can find Anna, and where they can find Ruby in her regular body.
The boys find Anna and Ruby at the hideout. Dean comes as close to apologizing to/thanking Ruby as he's able and Sam breaks the news to Anna about her parents' death. In the midst of sobbing, she looks up, says, "They're coming," and the lights dim. Sam hides her in a back room, while Ruby tries to secure the door, and Dean and Sam arm themselves and prepare for the onslaught of...
...angels! It's not demons, sillies -- of course, because Anna hears angels, not demons. It's Castiel and Uriel, who calls Ruby a "stain" -- which makes "mud-monkey" sound like a term of endearment. Dean hopes they're there to help. Castiel says they're there for Anna. Sam asks if they're going to help her. Castiel says, "No. She has to die." And damn it, we fade to black and get slapped with a "TO BE CONTINUED..." title card.
Coming up next week; we get to see another Winchester have sex, and it's not with Ruby. Oh, boys, don't you know these things never end well?
NOW! which rhymes with Wow, which is what we get in "I Know What You Did Last Summer." Anna Milton is at the Connor Beverly Behavioral Medicine Center. She sits on her bed and listens to unintelligible whispers, until her therapist calls her name. The therapist exposits for us that Anna is there because she became hysterical and it took four people to restrain her. Anna says that she understands everyone thinks she's nuts, but "It's all true." The therapist says, "It's okay. You can tell me. I'm here to listen." Don't do it, Anna. Anna can't keep her peace any longer. "The END is coming. The apocalypse." She tells her Lilith is trying to break the 66 seals necessary to free Lucifer from Hell, and he will bring the apocalypse. She adds, "So? Smoke 'em if you've got 'em." She goes back to listening to the angels. You'll never get out girl, if you let them know the truth. They can't handle the truth. The therapist calls her back to earth, and Anna apologizes, saying she was just listening. The therapist says, "So you were saying there are 66 of these seals in the world?" Anna says, "No, there are about 600 possible seals." (The closed-captioning reads 6000.) "And Lilith only has to break 66 of them, and no one knows which 66 she's going to break. That's why it's nearly impossible to stop her. That's why the angels are losing. That's why we're all going to die." You're gonna die in that ward, girl.