When he was sixteen, Dean met her while at reform school run by Sonny. Robin played the guitar and gave a few lessons to the boys at Sonny’s place and took an interest in Dean. With Robin, Dean confided in her about his dream of being a rock-star but admitted he might follow in the family business like his father wanted. She understood and revealed that while she had dreams of becoming a photographer, her own father wanted her to run their diner. Ever since he was four years old, Dean’s been charged with protecting Sam. After their mother was killed by a demon, Dean was forced to grow up quickly to accommodate their often absent father, and thus was thrust into the role of surrogate parent to Sam.
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While trying to protect Anna Milton, Dean unknowingly encountered Alastair again, this time in a vessel. Alastair reminded Dean of their time together in Hell, prompting the hunter to recall his name and look at him in disgust. It was this encounter that drove Dean to eventually reveal to Sam that he did in fact remember Hell. Dean later rescued Castiel from Alastair’s clutches when the latter tried to expel the angel from his vessel.
His Death
Appointment In Samarra – Dean died for seven minutes to contact Death in order to get Sam’s soul back. He was resuscitated by Dr. Robert as pre-planned though Doctor Robert almost couldn’t bring him back. No Rest for the Wicked – Dean is viciously mauled by Lilith’s hellhounds and dragged down to Hell due to a deal with a crossroads demon to resurrect Sam.
Even Crowley commented on his skills, stating that he knew Cain would be impressed by them and give Dean the Mark of Cain when Crowley himself wouldn’t be able to get it from him. In Lebanon, Dean meets an Alternate Castiel who was created by a timeline where John Winchester was brought to the future. This Castiel appeared on Earth with Alternate Zachariah, who was angry about the fact that somebody’s been messing with time.
Castiel also attempted to comfort Dean when they learn Benny was killed by vampires for his betrayal but Dean wouldn’t have it. Losing his patience, Castiel confronts Dean on his previous behavior about Mary and Jack, while Dean stayed firm in his behavior. However they are soon betrayed by the Leviathan who is determined to bring Castiel to Eve for his part in the Leviathan and killing the Alphas. Dean is knocked out and finds Castiel gone and looks for him almost forgoing leaving the realm on time. Losing himself in his grief, Dean starts to pray and apologize to Castiel about everything, and declared him as his best friend.
Dean thought Michael could open the God’s death book, so they could know how to defeat him. Both Dean and Michael are wary about the resurrected Lucifer siding with them. Michael even questioned if the Winchesters are seriously thinking about trusting his brother. After Lucifer reveals that he’s actually working for God and that he’s “sort of the new favorite now”. Dean watches him taunt Michael and watches the Archangels fight until Michael stabs Lucifer with an archangel blade, killing him once again. Dean first met Cassie in Athens, Ohio, where she was at college and he was on a hunting mission.
In Blood Brother, Sam tells Dean that Dean doesn’t have any friends because all of them are dead. Notably, Dean is responsible for the deaths of half the people listed here. In Destiny’s Child, Dean believes that due to the balance being off after Jack kills God, he should kill Amara.
Dean’s desperation continues to show even after Amara arrives and takes possession of Lucifer, who she proves is too weak to defeat her. He shouts for Castiel moments before Amara zaps herself and Lucifer away from the location. This failed attempt at rescuing Castiel does not, however, deter Dean’s resolve to help him. After a pause, Dean stabs a book next to Castiel’s head, then turns and walks out of the room, with a warning for Sam and Castiel to stay away from him, because next time he wouldn’t miss.
In Who We Are, Dean focuses on rescuing his brainwashed Mary and uses Toni’s reluctant help to do so. After speaking with his mother directly through her mind, Dean awakens to find Toni dead and Ketch standing above him. Dean shows no sign of calling Arthur until he becomes worried about Mary’s absence.
From her the brothers learn of the angel’s name, although seeing Castiel’s true visage resulted in her eyes being burnt out of her skull. Prior to this unfortunate event, Castiel had tried to communicate with Dean, but his true voice is beyond a human being’s capacity to hear and thus, failed to establish any meaningful contact. So yes, Dean’s relationship with his brother Sam might be a little codependent but one thing is for sure. The controversy still swirling around Castiel’s death partly derives from the ambiguity Cass’ “I love you” carries – somethingSupernatural’s cast has since muddied further.
Characters
In Caged Heat, Castiel exhibits more human urges, inadvertently watching porn, and later passionately kissing Meg, both to Dean’s discomfort. Castiel warns Dean that bringing Sam’s soul back could permanently damage the younger Winchester psychologically, but Dean remains firm on retrieving the soul. Castiel is banished with a sigil when they lay siege to Crowley’s warehouse, but later returns with Crowley’s bones, which he promptly incinerates when Crowley admits he can’t retrieve Sam’s soul from the cage. Later, when Castiel admits to Dean that he is on the losing side of the civil war in Heaven, Dean assures his friend that if he needs help, all he has to do is ask. In this season, Dean and Castiel’s friendship becomes strained, due to the war with Raphael, Castiel’s allegiance with Crowley and Sam’s soulless nature.
Neither of the facts was Dean aware of, and he suffered torture at Alastair’s hands for thirty long years, while resisting the offer each and every day to torture souls himself. mysinglefriend It is unknown if Azazel of the present remembered Dean, or if he ever met a time traveled Dean. What’s clear is that Azazel’s disregard for Dean led to his demise.
Dean soon joins Castiel on the hunt, but is displeased to find him working with Crowley. The four head to Los Angeles to try and prevent Lucifer from killing people while posing as the rock star Vince Vincente. Dean’s displeasure in Castiel and Crowley’s partnership shows when he complains about Castiel a few times. Castiel eventually encourages Dean to wear leather and fit in, by calling him “a lumberjack”. When they discover Lucifer’s plan to host a concert and where, Dean is visibly unhappy with Castiel’s decision to join Crowley in stalling Lucifer while Dean and Sam chase out the fans. Dean finds Castiel near a river and is happy to see his old friend who is now sane again.