I Know What You Did Last Summer is the 9th episode of Season 4. It aired on November 13th, 2008.


Dean Purgatory Blade.png There was something about being there... It felt pure.

This episode summary is an official CW press release. It may contain errors.

Ruby (guest star Genevieve Cortese) tells Sam and Dean that a powerful demon named Alastair (guest star Mark Rolston) is searching for a girl named Anna (guest star Julie McNiven) who can hear the angels' conversations. The three set out to find Anna but once they do, Alastair attacks them and Ruby escapes with the girl. Believing they were set up, Dean lashes out at Sam for trusting Ruby, so Sam tells him what happened during those months Dean was in Hell and how Ruby saved his life. Castiel (guest star Misha Collins) and Uriel (guest star Robert Wisdom) return and demand to be taken to Anna but not for the reason Dean thinks.



Anna was suddenly tuned to "angel radio".

The episode begins with an interview between Anna Milton and her psychiatric counselor at the Connor Beverley Behavioral Medicine Center where Anna is being held because she hears voices and has attempted to warn people that The Apocalypse is coming. She states that there are over 600 seals, and Lilith only needs to break 66 seals to release Lucifer, and that the angels are losing because they don't know which 66 seals Lilith will break. When a demon tries to accost her, she manages to escape, throwing a dresser at the demon using some form of psychic power.

Sam and Dean are at a bar. Sam is pretending to be drunk and he and Dean are running a hustle at pool. Sam makes a great break, but when he sees Ruby sitting at the bar, he tells the guy he's playing against to keep the $500 he wagered and makes his way over to Ruby. "Keep the money?!" Dean asks Sam incredulously. Dean follows Sam over to Ruby.


Dean is not happy to see Ruby again.

"You got a lot of nerve showing up anywhere near me," Dean says when he sees Ruby. Ruby tells him that she's just here to drop off some information then she's leaving. Ruby informs Sam and Dean that a woman called Anna Milton is being pursued by demons and that the girl must be pretty important because the demons orders are to bring Anna back alive.

Dean doesn't believe Ruby because he doesn't trust her whatsoever. He doesn't think Anna is real. They take off to find her, despite Dean's reluctance. Sam finds out that Anna is in fact real, but Dean says that doesn't mean the case is. Dean complains that its a three-day drive to the hospital, and Sam replies that he's driven a lot farther for less. Sam tells Dean that he's not pissed about going after the case, he's pissed about the fact that Ruby gave him the tip. "Right, cause as far as you're concerned, the hell bitch is practically family! Something must have happened while I was downstairs because I come back and you're BFFs with a demon?" Sam tells Dean that Ruby helped him go after Lilith, so he trusts her. Dean asks if he wants to elaborate, but Sam says "Sure Dean, let's trade stories! You first, how was hell? Don't spare the details." Dean shuts up.

Flashback to six months earlier, and Sam is at the crossroads, summoning the Crossroad Demon. The demon appears, saying he was reluctant to come because Sam shot one of his co-workers a few months back. The demon asks to see Ruby's Knife, and Sam pulls it out and puts it down. "No devils traps either," Sam says. "I'm not here to play games." Sam continues.


Sam tries to force his hand at the crossroads

"Let me guess, you want to make a deal? Round and round, The Winchesters go. Sorry, Sam, that's not gonna happen." The demon taunts. Sam visibly angers and quickly picks up Ruby's knife and stabs the demon in the hand with it. "I want to trade places with Dean!" Sam tells him. The Demon refuses. "JUST TAKE ME! ITS A FAIR TRADE!" Sam yells. The demon refuses again, and Sam asks why. "Don't you understand, Sam? It's not about your soul, Dean's in hell, right where we want him. We've got everything exactly the way we want it! You wanna kill me? Go ahead. I've made peace with my lord." The flashback ends.


The boys get Anna's sketchbook from her psychologist.

They speak to her doctor at the hospital, and find out she had been talking about demons and the apocalypse. Her sketch book reveals she knew about the breaking of the seals. Dean and Sam head off to Anna's house, only to find both her parents dead and sulfer residue on the ground. "What ever the deal with this Anna girl is..." Sam says. "...They want her and they're not screwing around." Dean finishes. Sam sees a picture on the fireplace mantle and asks to see Anna's sketches. "Check this out," Sam says. They realize that in one of Anna's sketches she was drawing the window of her church over and over. "If you were religious and scared, and had demons on your ass, where would you most feel safe?' Sam asks.


Alastair is tickled by Sam's attempt to exorcise him.

The brothers track her to her church. Anna recognizes them, the voices she hears are those of the angels and she has heard them talking about Dean, as the one who may save them. She reveals some of them don't like Sam. Alastair then appears. He is immune to Sam's powers, and beats Dean, who had encountered him in Hell. In the chaos, Ruby takes Anna to safety, even though Anna is scared because she can see Ruby's demon face. She can see the real face of every demon. Sam and Dean manage to escape by jumping out of a second-story window.

Back at the hotel, the boys tend to their wounds. Dean demands Sam tell him why he trusts Ruby. In flashback we find out that Sam tried to trade himself for Dean with a Crossroads Demon. Lilith then released Ruby from Hell, on the condition that she kill Sam. She instead kills the demon with her and tells Sam she is there to help him. A grief-stricken Sam rejects her help, and demands she vacate the body she is possessing.


Sam and Ruby reach a new level.

Ruby then possesses the body of a woman in a coma who is brain dead, and whose soul has left her body, and returns to Sam. She offers to help Sam use his powers so he can take revenge on Lilith and he accepts. He is unsuccessful at first in exorcising demons, and becomes even more despairing. Ruby tells him things will get better with time, and seduces him. Despite attempting to resist, Sam has sex with her (much to Dean's disgust). After that, Sam finds omens that lead him to Lilith and he pursues her despite Ruby's warning not to. Sam walks into a trap, and he's attacked by two demons until he is rescued by Ruby. She kills one with her knife and Sam successfully exorcises the other. Ruby saved his life, Sam tells Dean.


Ruby jumps the houskeeper to deliver a warning.

Back in the present, Ruby possesses the body of a maid at the hotel where Sam and Dean are staying in order to warn them that demons are closing in on them. She passes them the address of the cabin where she left Anna, tells them to exit through the bathroom window and to leave the car, then departs.

Once again, the angels drop in to deliver a death notice

Shortly thereafter, Sam and Dean meet up with Ruby and Anna at the cabin. When they sense someone approaching they assume it is Alastair, and Ruby asks Sam and Dean where the knife is—they have to admit that it was lost in the previous fight with Alastair. However, to their surprise, instead of a demon, Castiel and Uriel appear with Dean hoping they are here to help since they had demon problems. Uriel remarks he's sees that as he notices Ruby and insults her. The angels soon demand that they hand over Anna, with Castiel announcing, "We're here for Anna... she has to die."



Main CastEdit

Recurring CastEdit


Featured Supernatural BeingsEdit



  • The name of the episode is a reference to the 1997 horror movie of the same name.
  • Ruby enters a church (hallowed ground) in this episode, which—as established in Season 1's "Salvation"—isn't something "minor-league" demons can do. This indicates she's stronger than she lets on.
  • Alastair makes his first appearance.
  • Anna reveals that Dean is a symbol of hope among angels.
    • It is later revealed Dean is the true vessel of Michael who is destined to kill Lucifer.
  • This episode gave the name as well as the movie to the game genre named "I know what you did last summer" where the events that happen in later sessions are based on other sessions played before.
  • The building that serves as the exterior of the church where Anna goes to hide is St. Paul's Indian Catholic Church in North Vancouver. The same church is used in "Sin City."


  • Ruby: This body is 100% socially conscious. I recycle. Al Gore would be proud.

[When Sam reveals his sexual encounters with Ruby]

  • Dean: Sam.
  • Sam: Yeah.
  • Dean: Too much information!
  • Sam: Hey I told you I was coming clean.
  • Dean: Yeah, but now I feel dirty. Okay, well. Brain stabbing imagery aside, so far all you've told me about is a manipulative bitch who uh screwed you, played mind games with you and did everything in the book to get you to go bad.
  • Sam: Yeah, well there's more to the story.
  • Dean: Just skip the nudity please.

[Talking about the pros and cons of humanity]

  • Dean: Pain.
  • Anna: Chocolate cake.
  • Dean: Guilt.
  • Anna: Sex.
  • Dean: ... Ya you got me there.

  • Anna: Dean, do you know how many angels have actually seen God? Seen his face?
  • Dean: All of you?
  • Anna: Four angels. Four. And I'm not one of them.
  • Dean: That's it? Well, then how do you even know that there is a God?
  • Anna: We have to take it on faith. Which we're killed if we don't have.


  • Dean is chafed Ruby's presence, even more so by Sam's attention to her.
  • Sam casts a long shadow at the crossroads.
  • Sam warns Ruby to release the secretary she's wearing, or else he'll send her right back to Hell.
  • Ruby reenters Sam's life with "proof" that her vessel was vacant when she moved in.
  • Sam decides to follow Ruby's instruction to use his ability, to Dean's dismay.
  • Dean recognizes his tormentor.
  • Sam finds that the knife slows Alastair down only sightly.
  • Sam responds to Ruby's attempt to stop him from going after Lilith.
  • Dean tries to choke out a sliver of gratitude after finding that Ruby saved Sam's life.

International TitlesEdit

  • German: Ich weiß was du letzten Sommer getan hast (I Know What You Did Last Summer)


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