Dean and Sam are holed up in a hotel room. After Dean dozes off, Sam slips out and meets with Ruby outside. As they drive away, Ruby wonders if Sam's ready and Dean insists he's definitely ready.
Dean is having a dream of his time in Hell and wakes up to find Castiel sitting on the bed next to him. Castiel asks what he's dreaming about, and then tells Dean there's something he needs to stop. The angel then touches Dean's forehead and he passes out.
Dean wakes up on a park bench in an old-fashioned town. He doesn't have any luck picking up a signal on his cell phone and goes to a nearby diner. He runs into a teenager and asks for his help, but they guy doesn't know what a cell phone is. Dean determines he's in Lawrence, KS: his home town. Dean starts to notices discrepancies: everyone is dressed in clothing from the 1970s. Finally he spot a newspaper and realizes the date is April 30, 1973. An older man come in and talks to the teenager, and calls him "John Winchester." Dean realizes that the teenager is his father… 35 years in the past.
John notices Dean staring and wonders if they know each other. Dean denies it and thanks John for his help. The teenager leaves and Dean follows him, and runs into Castiel. Castile confirms that Dean has been transported through time and repeats that there's something Dean needs to stop. The angel disappears and Dean follows John to a used car lot where he's buying a VW van. Dean redirects him to a familiar-looking Impala and apologizes, but then starts asking if anything strange is happening in Lancaster. Creeped out, John tells him to go away but Dean apologizes and recommends he buy the Impala. Dean then steals a car and follows John as he picks up is girlfriend: Mary Campbell, Dean's future mother.
Dean follows them to a diner and listens in as they talk about their future together and the fact Mary's father Samuel disapproves of John. Mary leaves for the restroom and John gets out the engagement ring he has for her. However, Mary attacks Dean outside and clearly has fighting experience. He finally manages to get the upper hand... and sees a charm bracelet on her wrist. He realizes that she's a Hunter.
John drops Mary off at home and Dean is waiting for her. He's told her he's a Hunter and wants to meet Samuel. Samuel tests Dean on his knowledge of vampires, and Dean passes. However, Samuel orders him out anywhere, disliking Hunters. Mary's mother Deanna asks Dean to stay for dinner where he starts to get along with Samuel. Dean finally explains that he thought something was after John but it turns out he's wrong. Mary defends John, who Samuel considers a "civilian." Dean asks if anything unusual is going on and Samuel says he's working a local case of Tom Wiltshire, who fell into his combine and died. Dean suggests they team up to investigate but Samuel refuses.
The next day, Samuel goes to the Whitshire farm disguised as a priest and brings Mary along. She talks to Tom's son Charlie outside while Samuel goes to the door to talk to Beth Wiltshire. However, Dean is already there, disguised as a priest. After a few awkward moments, they talk to Beth together and she doesn't know of anything strange. However, Dean goes to find Mary and discovers that she's talked to Charlie and learned that he made a wish with a stranger to stop his father from beating him. In exchange, the stranger asked Charlie permission to visit him in 10 years. Dean thinks that Charlie sold his soul while Mary has Charlie describe the stranger. Dean realizes what's going on when Charlie says the stranger had yellow eyes.
Realizing that Azazel is involved Dean goes back to the Campbell house and warns them that they're all in danger. Going through John's future journal that he had with him, Dean finds the Colt with Daniel Elkins, a Hunter. The journal also documents Azazel's travels and his next victim is Liddy Walsh, who lives nearby. Samuel notices that Tom's death is listed and Dean lies that his father could see the future. Dean insists on killing Azazel even though Samuel thinks he's nuts.
As he leaves, Dean talks to Mary and says that she's destined to be with John. She admits that she loves John, and wants to be with someone who isn't a Hunter and will take her out of the life even if they have to elope. Dean, nervous, makes her promise to stay in her bed on November 2, 1983.
As Dean drives to Elkins' house, Castiel appears in the car with him and explains that Sam is busy in the future and won't miss Dean. The angel warns that if Dean alter the future, every person they saved will die. Dean doesn't care, refusing to let his parents die. He gets to Elkins' house but the Hunter confronts him with a shotgun. Dean begs to borrow the Colt and Elkins agrees.
Samuel and Mary are loading weapons when Samuel mentions that Dean is going after Azazel, who is targeting Liddy Walsh. Mary knows Liddy and insists on going to help.
Liddy is meeting with Azazel, who offers to cure her father in return for permission to visit her in ten years. She starts to agree… and Samuel comes in and blasts Azazel down with a shotgun. Unimpressed, Azazel telekinetically disarms and paralyzes him. Mary tries to attack and Azazel is impressed with her spunk. Dean arrives and tries to shoot Azazel, but the demon holds Mary as a hostage. She manages to break his hold but the demon leaves the host body in a cloud of black smoke before Dean can shoot.
Back at the Campbells' house, Dean tries to explain to Samuel that Azazel will kill marry if they don't kill it first. They're both unaware that Mary is outside, leaving with Dean.
Dean finally has to explain to the skeptical Samuel that he's Mary's son, Samuel's grandson, from the future. Samuel starts to believe him and they start to go over John's list. Samuel asks to see the Colt but Dean slides it away from him, inherently suspicious. Angry, "Samuel's" eyes glow yellow and he immobilizes Dean telekinetically. Azazel realizes that only an angel could have transported Dean through time. Smelling him, Azazel realizes that Dean isn't one of "his children," but has a brother who is. Sam is one of his personal psychic soldiers, and Dean realizes that Azazel is making his deals so he can give the children some of is blood and thus psychic powers. Azazel plans to make Mary one of his target. Dean notices Deanna trying to get to the Colt and keeps Azazel talking. He boasts that in the future he'll be the one that kills Azazel. Azazel is momentarily taken aback but boasts that his "endgame" is perfect and he has no intention of telling Dean what it is while angels are potentially listening in. Azazel then stabs his host body with a fatal wound: only his demonic essence is keeping it alive. Deanna, startled, screams and then runs for the Colt. Azazel telekinetically slams her into the wall. As she tries to crawl to the Colt, Azazel grabs her and breaks her neck. He releases his telekinetic grip on Dean and escapes, and Dean knows where he's heading.
John and Mary are parked on a street and John offers her the engagement ring. Azazel arrives, still in Samuel's body, and demands to know what's going on. He yanks John out of the car and then breaks his neck. Azazel then negotiates with Mary, offering to resurrect John in return for permission to visit her in 10 years. She demands to know why, and tries to get him to resurrect her parents, but he refuses. Azazel does promise that if no one interferes with him in 10 years, then no one will get hurt. She can make the deal and have the Hunter-free life she always wanted.
Dean arrives and finds Azazel kissing Mary. Before Dean can shoot, Azazel leaves Samuel's body, which collapses dead from the mortal wound. John comes back to life and Dean can only look at the reunited couple. Castiel appears behind Dean and transports him away. Dean wakes up back in the present, in his own bed. Dean wonders what the point of it all was and Castiel explains that the past can't be changed. He sent Dean back so he could learn the truth of Azazel's endgame plans and how it involves Sam. The angel tells Dean where his brother is and then warns that Sam is involved in something dangerous. Either Dean stops Sam… or Castiel and his fellow angels will.
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