This page is comprised of Dean Winchester's relationships over the years.
Dean meets Anna during the fourth season, and protects her from angels and demons and soon discovers that she is an angel herself. Anna is empathetic and sympathetic towards Dean for his undeserved suffering within Hell, and he feels he can relate to her unease of taking orders from an absent father. During Heaven and Hell, they have a moment together and hook up for the night. Dean protects her until the moment Uriel threaten Sam. Whenever Anna pops in, Dean is surprised to see her, but treats her kindly, even going so far as to compliment her appearance on one such occasion. They were on friendly terms until Anna goes back in time to kill Mary and John so that Sam could never born. Dean later witnesses her death at the hands of Michael.
Dean first met Cassie in Athens, Ohio, where she was at college and he was on a hunting mission. They dated a few times and became close enough for Dean to trust her with his biggest secret - what he did for a living. Confused and slightly freaked out, she ended their relationship, despite still being in love with him. When her father was killed, she contacted Dean for help and they eventually renewed their relationship by sleeping together, now that she saw the supernatural. However, their relationship could not progress because Dean soon left town again.
In Dean's fantasy world, Carmen was his live-in girlfriend. She was essentially what he wanted at the time. She knew almost everything about him (his favorite beer and foods). She also worked as a nurse and Dean was surprised he was dating a respectable woman. In the real world, she was a model in a magazine for his favorite beer.
Dying from an inoperable brain tumor, Layla and her mother were frequent visitors to Roy Le Grange's church in the hope that he would heal her. She met Dean and formed a friendship with him after he was healed, but Dean and Sam had to stop the 'miraculous' healing before Layla was cured. Had their situations been different, there was a chance of a relationship between the two.
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. She was his first romantic partner, as well as his first kiss. 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.
Dean promised to take her to the homecoming dance, though Dean's father forced him to leave the area. Dean also reluctantly broke up with Robin who was devastated by this.
Years later, Dean visited Cus's Place and was surprised to see Robin, who pretended she did not recognize him and he was sad by this knowledge. While visiting Sonny's place, Dean found Robin with Timmy, a boy who was being haunted by a ghost. Dean asked Robin to trust her of the danger but she was reluctant to have anything to do with Dean and revealed she remembered him but Dean forced her to cooperate as he tried - with Timmy's help - to convince the spirit of Timmy's mother to move on. Robin was shocked by the sight of an actual ghost and that Dean fights monsters everyday. She was nearly attacked but watched as Dean protected her and convince Timmy to have the ghost move on and was successful.
Before they parted ways again, Robin remarked on Dean's job and realized why he left. When he tried to apologize, she revealed her support of his activities after seeing his effect on Timmy and states that he is living an interesting life. She forgives him for the past and kissed Dean on the lips, and bid him farewell.
Dean spent more than two decades training as a hunter in order to defeat Azazel and avenge the death of his mother Mary. Once Dean's father John got his hands on the Colt, Azazel sent Meg after them in order to retrieve it, while Tom kidnapped John. Dean and Sam managed to trap Meg and exorcise her while Dean killed Tom with the Colt.
After Dean and Sam rescued John, Azazel revealed himself to be in possession of their father and pinned the two of them to opposite walls. Azazel expressed a desire to murder Dean with John's own hands in retaliation for what Dean did to Meg and Tom, revealing the pair to be his own children. Azazel even admitted that he could have killed Dean a thousand ways prior to this meeting.
Azazel eventually fled John, but came back when John himself offered his own soul in exchange for resurrecting Dean, who had ended up in a coma. Azazel's rage towards Dean for what he did to his children made Azazel hesitate. Upon accepting the deal, Azazel possessed Tessa and resurrected Dean, calling it his "lucky day". Azazel's agreement to bring back Dean was partially due to the belief that Dean was not a threat.
This act would come to haunt Azazel when, in their final confrontation at Wyoming, Azazel intended to kill Dean using the Colt, only for John's spirit to distract him long enough for Dean to retrieve the Colt and shoot him in the chest, killing the demon and avenging his mother.
At the behest of Castiel, Dean was later sent to the past where he encountered Azazel again. Unaware that Azazel had taken possession of his grandfather Samuel, Dean revealed that he had time traveled from the future, that he was Samuel's grandson and that he intended to kill Azazel. When Azazel finally revealed himself, Dean swore that he was the one that was going to kill the demon, though like his present counterpart, Azazel simply brushed him off.
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 would not see Azazel again until two years after his travel, when djinn poison made him hallucinate seeing the demon one last time.
Dean met Alastair after he was dragged off to Hell by a hellhound. The demon had been assigned to torture Dean and convince him to torture other souls in order to break the first seal binding Lucifer to his prison, the very thing Alastair had done to John a year earlier. 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.
After thirty years, Dean gave in and tortured souls, with Alastair teaching him how to perfect the art during the ten years Dean was with him. After that, the angel Castiel rescued Dean from Hell, bringing Dean with him the horrid memories of his suffering and the suffering he caused to others. According to Dean, he enjoyed torturing souls and it left him feeling a great deal of shame towards himself.
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. In response, Alastair suffocated Dean and Sam.
Dean encountered Alastair again briefly at a cemetery, and would come face to face again in an effort to prevent Alastair from breaking another seal by killing two reapers. Sam and Dean managed to rescue one reaper while the angels captured Alastair. Much to Dean's horror, he was asked by the angels to torture information out of Alastair, despite Dean's insistence that he did not believe he would come back out the same. Alastair resisted the torture and went on to inform Dean of the purpose of his suffering in Hell, and what had happened to John during his own time being tortured.
This broke Dean, who after ending up in hospital due to wounds inflicted by Alastair, refused to have anything more to do with Heaven. The guilt of what he had caused by breaking the first seal drove him to tears. By then, Alastair had been killed by Sam, thus freeing Dean from anymore chances of running into his torturer.
Upon their first meeting, Dean and Abaddon developed a hatred for each other, with Dean attempting to kill Abaddon with the demon-killing knife to no effect. After defeating Abaddon with his grandfather's help, Dean is shown to enjoy the idea that Abaddon will be forever trapped due to their inability to kill her. His hatred may have intensified since she killed his grandfather.
After Abaddon escapes, she tries to get Dean to give her the location of Crowley and tells him that she finds Dean a worthy vessel. Dean remains defiant in the face of her threats and afterwards, grows somewhat obsessed with the idea of killing her, particularly as it will give him access to the First Blade and allow him to "feed" the Mark of Cain. After holding the First Blade for the first time, Dean begins to obsessively search for Abaddon to feel the Blade's power again. During their final battle, Dean snarls as he kills Abaddon with the First Blade and then viciously attacks and mutilates her body after she's dead before being snapped out of it by Sam. By doing this, Dean avenged his grandfather as well as getting the satisfaction of ending her threat.
Dean meets Arthur Ketch for the first time in LOTUS, unaware that Arthur had been stalking him for the past couple of days, though Dean did notice Arthur's motorcycle. Due to Dean's conflict with Toni, who is a co-worker of Arthur, a few weeks back, Dean is suspicious of Arthur's motives and does not open up to him, though Arthur does attempt to intrigue him with his own weaponry. Although he is indeed fascinated, Dean's distrust drives him to ask Castiel to confirm whether Arthur is lying or not.
Dean and Sam decide to borrow one of Arthur's gadgets in order to deal with Lucifer. Shortly after, Dean and Sam are captured and taken prisoner for six weeks by the Secret Service. They manage to escape with Billie's help, and Dean meets Arthur again when the latter shows up with Castiel and Mary, who had come to take the brothers home. Dean remains distrustful of Arthur despite his help.
The two meet again in The Raid, when Arthur arrives at the Bunker and offers a drink, despite Dean's unwillingness to let him in. Arthur offers to take Dean on a hunt, and Dean agrees on the account that he is bored. However, while they are trying to hunt down a vampire nest, Dean witnesses Arthur's enjoyment in the act of torture, when Arthur beats on a single, defenseless vampire whom Dean is forced to kill, since he knows Arthur will hunt her down and hurt her some more if he lets her go.
Arthur believes that both he and Dean are killers with a shared passion for shedding blood. Dean doesn't think so, and his disgust in Arthur only grows massively after this encounter. Arthur's purpose for meeting Dean however, is to try and recruit him. The lack of success is blamed on Mick Davies.
After Mick is killed for failing again to recruit Sam and Dean and any American hunter to the Brits' cause, Arthur takes over as a medium between the Winchesters and the organization. At first, he pretends to be Mick and installs wiretapes inside the bunker, as Sam and Dean are now targets. He searches Dean's room and steals a photo of Dean and Mary.
When Arthur lies about Mick going back to London and announcing himself as the man they must contact now, Dean is visibly not pleased by the news. In fact, Dean's dislike in Arthur drives him to insult Arthur's motorbike, an insult Arthur hears through the wiretapes.
Dean shows no sign of calling Arthur until he becomes worried about Mary's absence. When Dean finds out from a letter from Eileen Leahy that there might be wiretapes in the bunker, Dean and Sam search for it and use it to lure the Brits into a trap. The brothers capture Lady Toni Bevell at the location. Much to Dean's disgust, Toni reveals that Arthur had "the best sex of his life" with Mary. When the trio return to the bunker, Arthur arrives and begins a shooting match, which ends in Arthur's defeat, until a brainwashed Mary rescues Arthur.
Seeing Toni as expendable, Arthur leaves her to die with the Winchester brothers while he sets the bunker to gradually drain of oxygen, effectively killing the trio while he traps them insde. Arthur leaves with Mary, a sight that devastates Dean. 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.
The two get into a brutal fight. Ketch taunts Dean while he beats on the injured hunter. Dean retaliates, and admits to knowing Ketch was a psycho but never thought him stupid. Ketch denies being stupid, but before he shoot Dean, Mary awakens from her trance and shoots Ketch in the shoulder, saving Dean. Ketch confesses that he knew both of them were killers, something which Dean agrees upon before Mary shoots Ketch dead.
After Arthur's resurrection, Dean is the most suspicious and untrustworthy of "Alexander's" story based upon what he knew of Arthur. Dean continually questions Arthur's story and the validity of it and refuses to trust him at all. Dean's past experiences with Arthur ultimately let him see through his lies and expose "Alexander" as Arthur after all. Even when Arthur saves his and Sam's life and appears to try to make amends, Dean refuses to hear Arthur out and makes an immediate failed attempt to kill him once more.
During the search for Lucifer, Dean encounters Arthur again and shrugs his offer to team up before Castiel incapacitates him and he is loaded up in the trunk. Dean wanted to question him and kill him after he gets answers. When Lucifer nearly killed Team Free Will, Arthur escaped the trunk and came to their aid and the archangel retreated from the area. The Winchesters questioned Arthur on his help, as he explains he has to draw the line somewhere and again offers to help them. To prove his sincerity, he reveals he is working for Asmodeus and can act as a double agent for the Winchesters since he knew of Lucifer and the invading Michael's threat. He even tells them to murder him once they resolve both problems and everything is safe and sound.
When questions are raised over Arthur's true intentions, Dean makes it clear he will kill Arthur if he tries to betray them and appears intent to kill him when they are done working with Arthur anyway.
In The Thing, after returning to the bunker with Seal of Solomon, Dean and Sam find Arthur waiting for them. They hold him at gunpoint but he reveals the battered Gabriel, which shocks the brothers. Dean accused Arthur of hurting the angel but he explains Gabriel's captivity by Asmodeus until Arthur rescued him. Arthur proved useful in this moment as he supplied the brothers with an archangel for the spell, as they needed Gabriel's grace. Arthur presented Asmodeus' next dose of Gabriel's grace, stolen along with the archangel blade both of which he offers for sanctuary at the bunker since Asmodeus will chase him to the ends of the Earth for his actions. Dean agrees to Arthur's proposal since it can potentially help them get their mother and Jack back. His decision shocked Arthur who silently accepts.
As the Winchesters prepare to open the rift to Apocalypse World, Arthur arrives and announces that he'll join Dean. To Sam's surprise, Dean agrees to allow Arthur to join him when he won't allow Sam. Dean tells Sam that he doesn't care if Arthur survives or not unlike Sam and in fact hopes he doesn't, something that Arthur takes in stride.
In Bring 'em Back Alive, working together in Apocalypse World appears to change Dean's opinion of Arthur. While initially hostile towards the man, Dean intervenes to save him from a bounty hunter and in return, Arthur saves Dean's life from the bounty hunter's poison. Dean goes so far as to open up to Arthur about his guilt over the murder of Charlie Bradbury and Arthur returns the favor by explaining his own guilt and remorse over not trying to save his friends. During the Liberation of the Silo, Dean fights side-by-side with Arthur, trusting Arthur to have his back without hesitation. When Arthur chooses to remain in Apocalypse World, Dean is noticeably reluctant to leave him behind.
In Exodus, Dean kills an angel that has been torturing Arthur and supports him when Arthur is too weak to stand up on his own. Arthur warmly greets Dean and cracks a joke about how "its about bloody time" that Dean rescued him instead of the other way around. Aside from being a bit off-put by their close proximity, Dean otherwise doesn't react. Dean shows no hesitation to work with Arthur and trusts him to the point that he sends Arthur and Castiel to lead the way through the rift back to the bunker without hesitation.
Dean is like a father to Ben, who shares many similarities with him. At first Dean thinks Ben is his son, but Lisa tells him otherwise. Later on, Dean shows Ben how to take down a bully and rescues him from changelings. Ben is shown to look up to Dean a lot.
A couple years later, Dean comes to live with Lisa and Ben, saying that when he sees himself happy, it's with them. Dean lives with Ben for a year. Dean also fears that Ben is too much like him. Dean makes sure Ben doesn't get near anything related to hunting. Dean even gets angry and yells at him when Ben touches his guns. Ben continues to admire Dean, calling him for advice when he breaks something and doesn't want to tell his mom. Dean advises him to man up and take responsibility for his actions. When Dean, then a vampire comes to say goodbye, Ben is excited to see him, but Dean shoves him against a wall as he's afraid of feeding on him. Ben is unable to even talk about the experience with Lisa, though he seems to forgive Dean. Dean shoving Ben contributes to his and Lisa's breakup. When Lisa starts to go on dates, Ben tricks Dean into coming back to try to get them back together and is upset when they don't. Ben tells Dean that he is abandoning his family by leaving them, showing that he probably sees Dean as a father. Dean does leave again, but is upset by the state he left Ben in, telling Sam that he left Ben heartbroken.
When demons arrive to kidnap him and his mother, Ben quickly calls Dean who becomes obsessed with rescuing them. During the rescue, Dean hesitates to do anything when the demon-possessed Lisa uses Ben as a hostage, but manages to free him by throwing holy water in her face. Dean also tells Ben to ignore the demon's taunts that Lisa doesn't love him. Despite this, Dean nearly suffered from a taunt when the demon said he was Ben's real father before stating Lisa doesn't even know. Eventually, Dean goes against his beliefs and lets Ben use a shotgun to hold the demons off so he can carry Lisa to safety. Later at the hospital, Ben is so distraught and traumatized by what happened that he coldly ignores Dean's attempts to console him. Wanting to protect him and Lisa, Dean has Castiel remove their memories of him after healing Lisa. Ben thus completely forgets who Dean is.
Dean Winchester and the vampire Benny became brothers in arms in Purgatory. At first meeting, Dean didn't trust Benny despite the fact that Benny saved his life until the latter told him of a way to escape. Dean forced Benny to help him find Castiel first before they escape. Together, they located him and began to fight their way out and Benny earned Dean's trust afterwards. Upon reaching the portal out, Dean keeps his end of the bargain and takes Benny's soul with him back to earth. Outside, they agree to go their separate ways, and that Benny should keep his nose clean to stay out of trouble.
In Blood Brother, Benny calls Dean for help and he helps him take down his old nest. While Dean initially distrusted Benny, he grew to trust him absolutely at some point, presumably after he saves Castiel from a Leviathan despite his dislike for him. By the time they are ready to escape Purgatory, Dean tells Benny that he has earned a lot of trust from him. At one point he tells Sam that Benny is the only person who has never let him down. Dean's trust in Benny goes so far that he defends Benny when it looks like he fed on humans, believing his story even when he catches him red-handed burying another victim about it being another vampire. He goes so far as to send a fake text from Amelia Richardson to Sam to get him out of the way and defends Benny's killing of Martin Creaser as self-defense, knowing that the mentally-unstable Martin had been after Benny and having gotten the story from his great-granddaughter. However, when Sam made Dean choose between them, Dean ultimately chose Sam over Benny and cut all ties with him, something Benny was understanding of despite his deteriorating situation.
In Taxi Driver, after learning that Sam is trapped in Purgatory, Dean calls Benny to rescue him. Dean's plan is to kill Benny to send him back so he can lead Sam and Bobby out the same way he did Dean and come back with Sam. Dean knows that he is asking a lot, but Benny agrees without hesitation, telling Dean he doesn't fit in on Earth anymore. Benny agrees to come back with Sam, but secretly plans not to return, keeping this from Dean. Dean kills Benny who rescues Sam and Bobby as planned, but stays behind to hold off other vampires. Dean is devastated to learn that Benny didn't come back with Sam and buries his body instead of burning it so he can possibly bring Benny back in the future. Benny's sacrifice earns him Sam's trust and he agrees to Dean's action, ending the animosity between Sam and Dean about Benny.
In The Werther Project, when under the influence of the Werther Box, Dean hallucinates that he is back in Purgatory with Benny who he is glad to see until he realizes that Benny isn't real. Dean kills his hallucination of Benny to return to the real world, though he does this knowing full well that it is not his friend that he is killing.
|“|| Dean: Tell me, I don't have to do this! Tell me you can stop!|
Cain: I will never stop.
— Dean's last conversation with Cain
in The Executioner's Song
Dean learned he was a descendant of Cain from Michael. He also learned because of this lineage anyone related to him can serve as a vessel to the Archangel.
However, he first meets Cain while hunting for the First Blade and was shocked to hear he was alive. He is further shocked when Cain prevents his and Crowley's escape. Dean then hears of Cain's reputation as a demon and was shocked that he knew of who he was in their meeting.
Dean is also put off by him sacrificing his own brother Abel and is disgruntled by the demon's unwillingness to help at first. However, he was sympathetic towards Cain's loss but is undeterred in his attempts to get the First Blade from Cain to kill Abaddon. On Cain's end, he is intrigued by Dean, having heard stories of him and admires his skill and determination. Eventually, Cain agrees to give Dean the Mark of Cain and asks in return that Dean kills him someday after killing Abaddon. Dean watched in awe, as Cain slaughtered Abaddon Loyalists single-handedly.
After learning that Cain has returned to his old ways, Dean becomes determined to kill Cain despite the fact that doing so could result in him falling completely under the Mark's influence. When Dean and Cain come face to face, Dean notes that Cain had asked Dean to kill him in the future, but Cain is dismissive of this and tells Dean he believes he is doing Dean a favor by killing him. Cain states he cares for Dean but stated a prediction of what he thinks is to come for Dean rattles him and after defeating Cain. Though Dean could have immediately ended it, he asks his ancestor if he can stop so he doesn't have to kill him. When Cain refuses to stop, Dean kills him but is left conflicted by Cain's predictions about him killing Crowley, Castiel and Sam due to the Mark if left unchecked.
Dean first meets the Leviathan in the form of Dick Roman when they are investigating the so-called Jersey Devil and realize Dick is a Leviathan. They first meet face to face when Sam and Dean rescue Bobby from him which results in Bobby getting fatally wounded. While Bobby is in the hospital dying, Dean confronts Dick outside, promising to kill him and pointing out that Dick can't kill him there as there is a crowd. Dick is simply amused by his threats.
Bobby's death sends Dean into an obsession with Dick and finding a way to kill him, which is apparently impossible. Dean spends three weeks learning all he can about Dick and his activities and hires Frank Devereaux to track his movements. Dean's obsession with Dick takes over his life to the point that when he's not working on a case, he focuses solely on Dick rather than his usual pursuits, worrying Sam. However, when confronted by Dick while rescuing Charlie Bradbury, Dean chooses to flee rather than fight as he can't kill him yet. After learning how to kill Dick from The Word of God, Dean grows more obsessed with getting him as he finally has a way. After Bobby turns into a Vengeful Spirit over his own obsession with killing Dick in revenge for his murder, he tells Dean to kill Dick, but not for vengeance, but for the job. Dean finally loses his obsession on the matter, but is still determined to kill Dick in order to stop the Leviathans and save the world.
When finally face to face with Dick armed with the one weapon that can kill him, Dean keeps his cool despite Dick's taunts, having apparently taken Bobby's request to heart and uses his smarts against him rather than brute force. Thanks to this method of confronting his most hated enemy, Dean is able to catch Dick off-guard and finally kill him with the help of Castiel who restrains Dick for him. However, as a side-effect of killing Dick, Dean and Castiel are dragged to Purgatory themselves with his essence where Dean remains trapped for a year. Despite encountering several Leviathans in Purgatory, Dean apparently never encounters Dick again after his death. Dean killing Dick also effectively ends the threat of the Leviathans as it leaves them completely disorganized as Dick is the only leader they have ever had. The Leviathans revert into ordinary monsters, just harder to defeat and at least most of them are brought down by demons under the command of Crowley once Dean has dispatched their leader.
|“||Please don't let him hurt me.||”|
— Emma's last words to Dean
Dean's only known biological child is an Amazon by the name of Emma. During a case, Dean had unwittingly conceived her with her mother Lydia. As an Amazon, Emma grew quickly and was born within two days after conception. Dean had the fortune of meeting the girl while she was still a toddler, but he didn't know at the time that Emma was his until he did an investigation on Amazons. Dean was shocked to realize he produced a child and didn't like Sam's jokes about being a father.
Once Emma turned sixteen, she was assigned with the task of killing her father and uncle. Emma lied to Dean about running away from the Amazon leaders so he would drop his guard, but Dean knew it was a trap and held her at gun point before she could stab him. Emma was impressed with him as she was told that he was a challenge.
Both Emma and Dean knew that Dean was too soft and could not bring himself to kill Emma, his own child, leading Sam to shoot Emma in order to save Dean. This left Dean noticeably upset in the following weeks, but he soon came to forget, or simply not think about, his daughter. It is unknown if Dean considers her to be a family member or just another monster, given Dean's unforgiving attitude towards monsters in general. However, he has made it so he won't hook up with random women and make another child.
Dean first meets Gadreel when he prays for help to save Sam and the angel comes to answer his prayer. Dean kills an angel that beats down Gadreel, saving him, but not trusting him, Dean traps him in Holy Fire. After Gadreel identifies himself as Ezekiel and Castiel confirms that "Ezekiel" can be trusted, Dean lets Gadreel work on saving Sam. Eventually, desperate, Dean tricks Sam into saying "Yes" to Gadreel so the angel can heal him from the inside. Though Gadreel allows Sam to have control, he periodically emerges to aid Dean at times though Dean covers these times up so Sam won't expel Gadreel and die. Dean calls on Gadreel to help locate Castiel when he is being hunted by Reapers and Gadreel resurrects Castiel and Charlie Bradbury for Dean despite knowing it will weaken him because their deaths affected Dean badly. However, over time, Dean grows less trusting of Gadreel, especially after encountering Chef Leo who allowed something in and it ended badly when he lost control and due to Gadreel's reaction to Castiel's presence. After Gadreel promises him that there is not much time left before Sam is healed, Dean pushes him to hurry up and grows more and more suspicious as Gadreel tells him that Castiel is a threat because angels are after him when Dean knows that no one knows that Gadreel is in Sam. However, he has no choice but to comply with the angel's demands as he will leave Sam otherwise and he might die.
When Dean learns that the real Ezekiel is dead from Castiel, his suspicions are confirmed and he uses a sigil to try to suppress Gadreel so Sam can expel him. This backfires and Dean is forced to watch as Gadreel takes full control of Sam, murders Kevin and leaves. Dean ends up having to team up with Crowley to save Sam, again going to desperate measures to get rid of the angel he once trusted despite Gadreel's threats to harm Sam if they attempt to expel him. Dean goes as far as allowing Crowley to torture Gadreel and even possess Sam to force the angel out. Finally, Crowley succeeds and Gadreel is expelled but Dean's relationship with Sam is severely damaged by the event and Dean decides to hunt by himself to prevent anyone else from getting hurt by him, something Sam doesn't even try to stop. After Gadreel is captured, Dean tortures and nearly kills him under the Mark of Cain's influence, but ultimately spares his life and trades him for Castiel. When Gadreel changes sides and asks for a second chance, Dean pretends to forgive him, but his own anger augmented by the Mark of Cain causes him to try to kill Gadreel with the First Blade, leaving Gadreel seriously wounded. Despite Sam's insistence that Gadreel is their one chance to beat Metatron, Dean shows no remorse for his actions.
Dean met Garth in Season Seven, Time for a Wedding! when Bobby sends the latter to help. Dean is not too impressed by Garth's clumsiness and his apparent inept attitude. However, he changes his perspective when Garth protects someone from the demon Jackson and successfully trapping Guy in a devil's trap. After the conflict was resolved, Dean told Garth that he didn't suck though is dismayed by a hug from him. Dean was also annoyed by Sam's remark on making a friend.
In later seasons, Dean continues to rely on Garth in cases such as having him protect Linda Tran and her son Kevin Tran as well as for finding his grandfather Henry Winchester who time traveled to the future. Dean now seems to regard Garth as a friend as he was worried when he went missing and was sad to see he was now a Werewolf. However, Dean accepted Garth and believed he could keep himself under control. He even allowed Garth to hug him before he changed his mind, while being pleased Garth found happiness with his new family.
In Who We Are, Dean contacts Garth and warns him about the threat from the British Men of Letters. Knowing that Garth would be a prime target because of his status as a werewolf, Dean orders him and Bess to hide until its safe.
During The Spear, Dean was worried for Garth's safety when he heard Sam act as a mole in Michael's army. Garth also told Michael that he still is Dean's friend when the latter recognized as such. After learning Garth took Michael's grace, Dean wondered if they could truly save him.
|“||My mom is my hero, and I miss her, and I will miss her every day of my life, but she would not want this. (...) This isn't just a story; it's our lives! So God or no God, you go to Hell!||”|
For most of his life, Dean lacked faith in God, he felt this way after his mother's death and for all the pain that befalls people with the supernatural. Though he noted that the freak death of a human criminal seemed like "an act of God." After Castiel resurrected Dean and told him that God had ordered it, Dean was shocked but continued to lack faith as he didn't believe he was worthy of saving and couldn't understand why God would do it. He even stated his reasons to Sam and Bobby but only calmed down after they informed he was lucky to be alive again. After the failure of their plan to kill Lucifer with the Colt, Dean placed his faith into Castiel's plan to defeat Lucifer by finding God but lost his faith in everything when God, after sending Joshua to save them, told Sam and Dean through Joshua that he had no intention to help them further.
Before this, as stated by Joshua, God had helped the Winchesters by teleporting them onto an airplane as Lucifer rose, resurrected Castiel to help them in the battle and granted them salvation in Heaven after Walt and Roy killed them. After the Apocalypse is stopped, Dean is disgusted when Castiel has a renewed faith in God and states "if you see him tell him I'm coming for him next." Castiel realizes that Dean is angry which he confirms he is since God resurrected Castiel again but Dean just ended up with "my brother in a hole."
As Chuck Shurley, Dean was at first aggressive towards God before he was revealed as a Prophet and at first disbelieving about his prophetic books. However, he later turned to Chuck as a source of information for finding the locations of where Sam was confronting Lilith and the final battle between Michael and Lucifer. Despite this though, he threatened Chuck about not making anymore books during a fan convention.
After Chuck reveals himself to be God to the Winchesters, Dean refuses to believe it's actually him until God teleports them to the Bunker and calls in the spirit of Kevin Tran before he sends him to Heaven, proving his claims.
Dean was very shocked to actually meet God being silent in the meeting with him but unlike Sam who is awed by God's presence, Dean is a little more bitter due to God's refusal to help with problems in the past and his apparent lack of care about humanity. As God explains his reasons, Dean gets visibly emotional and starts crying. God eventually tells Dean to stop putting his abandonment issues with his father on him, as the latter looked at him with a sad expression. When God steps out as Sam and Dean talk about a plan for Amara, he states he always had faith in them before he pokes fun at Dean's previous lack of faith.
After learning from Metatron of God's plans to sacrifice himself to Amara, Dean tries to talk him out of it and is shocked to learn that God sees him as the "firewall" between Light and Darkness. Dean tried to say he couldn't handle such a thing but God tells him he knows he can since that was why he had Castiel save Dean from his torment, causing Dean to have a different perspective of him.
After God is mortally wounded, Dean manages to save him in the end by convincing Amara that revenge isn't worth it. Rather than killing Amara, Dean is able to get her to finally reconcile with her brother and end her long-standing grudge against him. In doing so, Dean uses his own relationship with Sam as an example of why Amara should forgive God. After God is healed by Amara, he removes the soul bomb in Dean and departs Earth with her, telling a curious Dean that he knows the Earth will be fine without him because it's got Dean to protect it.
Dean's opinion of God seems positive up until he loses his mother, Crowley and Castiel during a confrontation with Lucifer. Dean tries to get God to help and bring the three people back, and blames God for putting everything on his and Sam's shoulders. When God doesn't answer, Dean believes that God just doesn't care.
It appears he has still hasn't gotten over this as seen in A Most Holy Man where he tells Father Lucca Camilleri that he knows that God exists, but believes that God doesn't care about any of them and won't help. Lucca explains to Dean that he doesn't literally expect God to show up and perform a miracle but that he sees good acts as being God's work. This seems to cause Dean to let go some of his old pain.
Dean and Gordon meet in Season 2's Bloodlust. At first, Dean and Gordon hit it off pretty well, they even do a hunt together, though once Dean realizes how psychotic Gordon is, they become enemies. This is especially true when Gordon begins to hunt Sam down in Hunted. In that episode Gordon takes Dean prisoner. They remain enemies until Fresh Blood, when Sam kills Gordon. Dean later mentions Gordon's death to Lenore with a pleased tone, much to Sam's annoyance.
Henry is Dean's paternal grandfather. Dean first met him in As Time Goes By, when the latter time traveled to get away from a demon named Abaddon. After learning who he is, Dean was shocked to meet him as the latter was to meet him and Sam. Like with Samuel, Dean was distrustful of him and resented him for not being there for his father and does not accept Sam's belief that it wasn't his fault. Dean is also annoyed that Henry is disappointed in him and Sam not being in Men of Letters before criticizing him for abandoning his family.
After Henry reads John Winchester's Journal, he tries to undo his mistake and traveled back to his son. Aware that this would alter history, Dean stops him and admits to him that he was wrong to believe that he ditched his father after finally seeing that he was not entirely at fault. He forgave Henry in John's place.
When Dean learns Abaddon has taken Sam hostage in exchange for Henry, Dean immediately wanted to save his brother and knocked out his grandfather to bring him along. On the way, Dean earned Henry's respect by going out of his way to save Sam and calling him his only real family. This causes Henry to make a plan, though Dean was worried for Henry's safety as a result but the latter was insistent. The two were able to defeat Abaddon but at the cost of Henry who uses his final moment to express pride in them and their father.
The brothers then bury their grandfather in the cemetery of his fellow deceased Men of Letters, and realize the significance of all Heaven positioning the brainy Winchesters and brawny Campbells together to produce them.
Whether intentionally, Dean later avenged his grandfather by killing Abaddon under the influence of the Mark of Cain.
During Lebanon, Dean spoke fondly of his grandfather when talking to John who was pulled into the future and remarked he'd be proud that John made it to the bunker and learn of his legacy.
Dean first meets Kevin Tran when he comes to the hospital where an insane Castiel is incarcerated. Dean banishes Hester, Inias and Castiel to protect him and encourages him when he has trouble translating the Leviathan Tablet. After returning from Purgatory, Dean is upset to learn that Sam abandoned Kevin when he needed them, feeling that Kevin was their responsibility. However, Dean loses Kevin's trust when he is willing to sacrifice his mother to kill Crowley.
After he, Sam and Castiel rescue Kevin however, he seems to regain it. Dean keeps up with Kevin at Garth's houseboat, bringing him food and seeking his help with matters relating to the Trials of God and other things. Dean is also slightly stunned at the fact that Kevin cut his own mother off to be alone. When Kevin translates the first trial, Dean pushes him a bit hard in his efforts to close up Hell despite Kevin's clearly stressed condition, giving him pills to help keep him awake. When Kevin starts hallucinating Crowley, Dean encourages him and grows frustrated by his hiding of the demon tablet.
After Kevin's kidnapping and believed death, Dean grows upset, saying that they should've brought Kevin to the Men of Letters Bunker for his protection and berating Metatron for staying out of things, using Kevin's story to push him into action which results in Kevin's rescue. After getting the angel tablet, Dean again pushes Kevin hard to translate needed information and this and Crowley later result in Kevin nearly leaving the Bunker before Dean convinces him he considers Kevin to be family. Dean grows to rely on Kevin for information from the Bunker when needed, but doesn't let him in on the secret of Sam's possession when he learns that the angel possessing Sam is not Ezekiel and turns to Kevin for help in suppressing the angel so Sam can expel him. Dean can only watch, horrified, as Gadreel murders Kevin and later gives him a hunter's funeral. Dean swears to Sam that he will get revenge on Gadreel for Kevin's death, but also states that it is his fault and he believes he is going to Hell for letting Kevin die like that.
When Kevin returns as a ghost, Dean waits for him to manifest and does his best to apologize, something Kevin complains about when he finally becomes visible. Kevin asks Sam and Dean to rescue his mother from Crowley, telling Dean that its how he can make it up to him. After Linda is rescued, Kevin tells Sam and Dean he doesn't blame them and asks them to get Gadreel for him which they agree to. Kevin asks them to put aside their differences and be brothers again which Dean agrees to and seems about to try after Kevin's departure, but Sam simply walks away from him despite promising Kevin the same.
Dean and Kevin meet briefly in All in the Family, when God reveals that Kevin had been residing in the Veil for the last two years. Kevin tells them he has always trusted the brothers. God then delivers Kevin's soul to Heaven where it belongs.
During Devil's Bargain, Dean was shocked to hear from Castiel that an Alternate Kevin used a spell that allowed Lucifer to return and that the latter worked for Alternate Michael who wants to invade their world.
Dean was predestined to be the archangel Michael's true vessel, however Dean hated Michael, as Michael wanted to battle Lucifer, which would have led to the end of the world and the death of his brother. In return, Michael didn't really hate Dean, although he considered him inferior since he was a human. During Changing Channels, Dean learned he was Michael's vessel because his relationship to his father was similar to the latter's with his father. They first met when Anna Milton time traveled to kill Dean's parents and Michael possessed Dean's father John Winchester which allowed Michael to kill Anna. Dean realized who he was as they spoke and demanded he heal Sam (who was wounded by Anna), Michael stated he would after they talk. He went so far as explaining himself to Dean in an attempt to convince him to become his vessel, comparing his love for Lucifer to Dean's love for Sam. For a time, Dean considered letting Michael use him, but changed his mind as he didn't want to let Sam down. This forced Michael to take Dean's half-brother Adam Milligan as a vessel instead.
When Dean later saw Michael possessing Adam, he wished to apologized to his brother for his fate but Michael coldly told Dean that Adam "wasn't home right now". Dean then warned Michael that he was coming after him next, something Michael didn't take seriously. Because of Dean's refusal to play his part, Michael insulted him as he deemed him no longer part of the story, and attempted to remove him from Stull Cemetery. He was stopped by Castiel. Dean then watched as Sam tossed both himself, Lucifer, Adam and Michael into Lucifer's Cage.
Dean would not hear of Michael for several years aside from hearing from God and Lucifer that he went insane.
Dean and Alternate MichaelEdit
During Devil's Bargain, Dean has learned from Castiel that an Alternate Michael is coming to invade his world and was shocked to hear that his mother Mary Winchester and Jack are in danger. He has decided to find a way to save them before Michael harms them.
When going back to Apocalypse World in Bring 'em Back Alive, Dean witnesses the angels subjugating the humans to their will in Michael's name. He was angry to see the ruthlessness of angels in this world and likely detested the alternate Michael for his tyrannical rule.
In Exodus, Dean finally met this Michael and was shocked to see him even more so as he watched him easily tossed aside Lucifer. Dean's disdain for him most likely increased after he witnessed him kill Gabriel.
In Let the Good Times Roll, Dean was shocked when Michael managed to invade his world but knowing his threat level, Dean urged Sam and Castiel to run from him as he held him off with holy fire. Michael invaded the bunker as Dean and Sam shot at him but to no avail, Dean was attacked by him. Michael voiced his intentions to kill Dean first but Dean remained defiant against the Archangel by mocking him. Dean was rescued by Jack and watched him torture Michael. After Lucifer became super-charged and took Sam and Jack Dean turned to Michael for help as Michael was the only being left strong enough to defeat Lucifer. Remembering that he was Michael's true vessel, the Michael Sword, Dean offered a deal to Michael where he would say "yes" in exchange for Dean remaining in control while Michael powered him to fight Lucifer.
Thanks to their deal, Dean was finally able to kill Lucifer with an archangel blade. However, afterwards, Michael went back on their deal, took full control of Dean's body and took off to exact his own reign of terror on Earth.
In Gods and Monsters, Dean was possessed for weeks before he manages to manifest himself in a mirror and orders the archangel to get out his body. However, Michael was surprised at his act but bluntly refused and shatters the mirror, while telling Dean that he owns him. Despite that, Michael soon left on his own for an unknown reason.
During The Scar, Dean is still resentful of Michael for using him and seeks to kill him after learning of the spear wielded by Alternate Kaia that could harm him. Dean also revealed his guilt that Michael is now building an army of Monsters because Dean let him in and how Michael treated him in his possession by leaving him trapped and clawing for a way to gain control. He also shows a strong desire to obtain Kaia's spear and kill Michael. Dean is also angry at being compared to Michael as seen when he reacted to Alternate Kaia's taunts.
In Mint Condition, Dean's guilt over saying yes to Michael appears to have worsened as he hasn't come out of his room in almost a week, according to Sam. After Sam assures him that he did it to save Sam and Jack and that Michael taking control over Dean afterwards isn't his fault, it is unknown if Dean will be able to let go of his guilt.
Dean is also searching for the Archangel though is skeptical on how to defeat him as seen in Nightmare Logic.
In The Spear, Dean expresses a desire for revenge against Michael and when facing him, made sure to pay him back for using him as the latter states that all the imminent deaths will be because of Dean. The hunter tries to kill the archangel but fails as he is repossessed. Michael announces that his plan all along had been to break Dean's spirit and that it has worked with Dean trapped in his subconscious.
As of Nihilism, Michael kept Dean in a imaginary bar that Dean dreamed of owning with Pamela Barnes. While in reality, he tried to turn everyone against Dean by telling them his thoughts. Michael also regarded Dean as a gnat that he controls. After Sam and Castiel enter his mind, they warned Dean of the loop and he is reluctant to believe it until they remind him of his memories. When Michael appears, Dean orders him out but he refuses and a fight breaks out. Michael had the upper-hand though his boasting gave Dean an idea where he decides rather than eject him but keep him locked away, as he did to Dean. With help from the others, Dean puts Michael behind a locked door while he regains control of himself. Dean kept Michael in his subconscious, though senses Michael continuously screaming to be released. Dean seems unsure if he can keep him trapped, as seen when Billie warns Dean that Michael most likely won't stay trapped for long because of his potential release. According to Billie, in all but one possible version of Dean's ultimate fate, Michael escapes and uses Dean's body to destroy the world, worrying him particularly when Billie reveals what it is he must do to stop Michael.
In Damaged Goods, Dean builds a Ma'lak Box to trap himself and Michael at the bottom of the ocean forever as per the information he was given by Billie, seeing no other option for dealing with the threat of Michael who continues to try to break free of Dean's mind.
In Prophet and Loss, Sam and Castiel convince Dean to try to find another way first, though he plans to keep the Ma'lak Box as a last resort.
In Ouroboros, Dean reveals to Castiel that Michael is continuing to try to break free from his mind with Dean telling Castiel that its taking all of his concentration to keep Michael contained. As a result, Dean is barely even sleeping anymore, showing how stressed he was. After being knocked out by a Gorgon, Dean lost concentration and Michael escaped his mind. However, Michael no longer wanted to possess Dean but instead get revenge on him for humiliating him by taking Rowena as alternative vessel, stating it didn't work out between them. After Dean woke up, he questioned where Michael was before witnessing him slaughter the hunters in the bunker in Rowena's body. Michael taunted Dean on not sealing him away in the box but Dean wanted to do so anyway though Michael tortured Dean and his friends. Dean was saved by Jack and witnessed him fight Michael and expel him from Rowena, before incinerating him and taking his grace to replenish his own. With this, Dean was forever freed of Michael's influence and the world was spared being destroyed by the corrupt Archangel.
Dean met Mick Davies while under interrogation and torture by Mick's co-worker Toni. Unlike Toni, Mick presented himself as a friend and even took Toni away back to England.
Dean met Mick again while escaping Site 94. Mary and Castiel had asked help from Mick and Arthur in locating Sam and Dean. They did not interact and Dean only showed distrust in Arthur.
Dean was made aware Sam allied with them after Sam revealed this fact to him, Dean agreed to join the Brits out of trust for Mick. In order to gain field experience, Mick joined the brothers on a werewolf hunt, however, Mick's loyalty to the British Men of Letters code drove him to kill a teenager who was turning. This upset Sam so much he refused to speak to Mick or listen to any excuses, though Mick proved useful when he had a means to locate Claire Novak and cure her of her transformation.
Their relationship clearly improving, Mick was able to pay Sam and Dean a visit at the Men of Letters bunker and share a drink with them while they discussed Jack. Mick slept there for the night and joined them on a hunt for Kelly Kline, the child's mother. While Mick and his associate Renny Rawlings wanted the child aborted, Dean argued, preferring to deal with the baby differently. They were soon interrupted by Dagon, who came to take Kelly away. Eileen accidentally killed Renny in an attempt to kill Dagon, and Mick - ever loyal to the code - tried to kill Eileen. Although Mick was talked out of killing Eileen, his newfound dislike in the code led to his own death. The same happened to Max and Magda.
Dean does not find out about Mick's death until weeks later, when a captured Lady Toni Bevell casually tells him and Sam the truth. She even admits he was killed because he held sympathies for the Winchesters. Dean is visibly unhappy about Mick's death, having thought him alive and in London as told by Arthur Ketch.
Upon first hearing of Metatron, Dean misunderstood his name to be Megatron from Transformers and sought him briefly as a source of information on the Leviathan Tablet. Upon their first meeting, Dean was surprised by Metatron's physical appearance and grew angry with Metatron's inaction, yelling at Metatron and resulting in him rescuing Kevin Tran. Following Metatron expelling all the angels from Heaven, Dean became determined to stop him and was disgusted by Metatron's actions in turning a whole homeless camp to worshipping him to the point that they'd murder another angel. He also saw Metatron as only being "Bernie Madoff with wings." Following his death at Metatron's hands, Dean became vengeful towards Metatron, particularly under the influence of the Mark of Cain.
As a result, Dean nearly tortured Metatron to death. He was later angry at the fact that Castiel let the now-human Metatron go after capturing him again. Despite this, Dean was willing, albeit reluctantly, to hear Metatron out when he called them about God's autobiography. He later only let Metatron into the Men of Letters bunker when Metatron annoyed him into it with texts and emojis. When Metatron proposed working together to rescue Lucifer and explained his motives, Dean agreed to let him work with them and explained their plan to him. After Metatron's death, Dean expressed shock at his sacrifice for him but didn't seem too bothered by it.
The witch Rowena, like her son Crowley, has an on-and-off relationship with Dean and they usually work together only when it is absolutely necessary. Dean had attempted to kill Rowena during their earliest encounters, and it was Dean who encouraged Crowley to stop obeying his mother, leading Crowley to expel Rowena from his palace and forcing her to find a place for herself elsewhere.
Rowena was a key figure in removing the Mark of Cain from Dean's arm. It was she who was able to read the Book of the Damned that contained the spell. Shortly after the Mark was removed, Rowena fled, leaving Castiel trapped under a spell until Sam dragged her back and forced her to remove it.
Dean and Sam contacted Rowena again when Dean finally agreed to have Sam talk to Lucifer, in response to Sam's visions presumably from God. Dean inquired Rowena for a way to allow Sam and Lucifer to speak that would not pose any danger to Sam. To Dean's dismay, Rowena was already in alliance with Lucifer. This forced Dean to bind her with a witchcatcher and order her to send Lucifer back to his Cage. Dean went to confront Lucifer himself in hopes of buying Rowena time to complete the spell.
Weeks later, Dean discovered that Lucifer had escaped, taken Castiel as a vessel, and killed Rowena. However, the witch managed to bring herself back to life and had come to ally herself with the Winchesters in retaliation against the archangel. Their combined efforts failed to free Castiel of possession, and Rowena's short-lived alliance with Amara brought Amara to their location, who then kidnapped Lucifer along with Castiel.
Rowena returned to work with the Winchesters again after God enlisted witches as part of his team against Amara. Rowena remained loyal throughout the conflict with Amara, mainly due to her attachment to God. After his departure from Earth, Rowena left, only to come back once more to offer help in re-imprisoning Lucifer, which she ultimately succeeded in doing. Weeks after that, Sam called in Rowena to cure Dean of a curse that was slowly taking away Dean's memories.
During this time, Rowena and Dean got along, with Dean complimenting Rowena's "bouncy hair" and Rowena feeling hesitant about fixing Dean because of the way he now was. After she and Sam were captured by the Loughlins, Dean came to their rescue and save Rowena from being killed. Rowena then cured Dean of the curse, with Dean not remembering a single moment of his time while under the curse. However, he and Rowena shared a laugh at Sam's expense.
In Various & Sundry Villains, Rowena appeared and lifted the love spell off Dean, while he was shocked to see her alive.
Samuel is Dean's maternal grandfather. They first meet in In The Beginning when Castiel send's Dean back in time. Dean was amazed to learn his grandfather was a hunter and his mother was one as well. Samuel gives Dean a test to prove whether or not Dean is a real hunter and was pleased that he passed the hunter's test. Dean was surprised Samuel and his wife were his and Sam's namesakes. It appears Dean respected him, as Dean later tells "Samuel" that he is Samuel's grandson, unaware that he was being possessed at the time. He was also horrified to watch Azazel kill him.
Samuel later returns in season 6 and Dean is surprised to see him alive before he is hugged by him. Samuel explained his resurrection to Dean, which further surprised him. Samuel later saves Dean when he turns into a vampire by bringing him the cure that can turn him back instead of killing Dean as he expected. Samuel later noted Dean had Campbell blood in him after he destroyed a nest of vampires on his own and seemed proud. He spoke to him and realized Dean wanted a normal life with Lisa and Ben like his mother did with John.
Although, soon after, Dean begins to question Samuel and his morals. This soon turns to mistrust and Dean believes that he and Samuel don't hold family the same. Samuel later betrays Dean by selling them out to Crowley so the latter would resurrect Mary for him. Samuel spoke to Dean and told him he was a stranger as Dean tells his grandfather the next time he sees him, Dean will be there to kill Samuel, something that left Samuel shaken.
Dean later tries to act on his promise, in their next meeting but Sam stops him. Dean is still distrustful of Samuel and leaves out for alone time. After returning and calming down, Dean questions him on his actions, implying he would forgive him if the latter admitted his error. Samuel is unrepentant in his choice, though he seemed to have regretted his choice and understand why they want to kill him but refused to apologized. Dean promises to make good on his threat after the case. However, he was never able to finish Samuel off though, since Sam is the one to kill Samuel.
Despite his resentment of him, Dean was somewhat conflicted about his grandfather's death though he told Sam of what it means to be family and Samuel's actions did not warrant him as such.
It is unknown if he or Sam ever told his mother who was resurrected about Samuel's resurrection and his actions.
Dean first encountered the reaper Tessa in In My Time of Dying, while he was in a coma and Tessa intended to reap Dean's soul. Tessa pretended to be a young woman whose mother was dying, to earn sympathy from Dean, but Dean eventually saw through her disguise. Nevertheless, Tessa continued to pursue him into leaving his life, and almost succeeded before Azazel interrupted them. The possessed reaper then healed Dean and returned him to his body.
Dean would not remember this encounter after he woke up. It wasn't until two years later in Death Takes A Holiday that Dean met Tessa again. In a bid to stop a seal from breaking, Dean ventured into the Veil with Sam. Upon meeting the reaper, Dean asked who she was after Tessa acknowledged him before she kissed him which granted him back the memories of their first encounter. Dean and Tessa talk about his resurrection by Castiel. He later proceeded to rescue her from Alastair. Tessa also gave Dean a vague warning about the angel's intentions, which left him pondering.
In Appointment In Samarra, Dean attempted to summon Death to get Sam's soul back, but Tessa arrived to reprimand him. Death however, agreed to retrieve Sam's soul if Dean became Death for a day. Tessa was the one to guide Dean throughout this period.
They do not meet again for a long while. Dean, in a bid to capture Metatron and stop the suicide-bombings, captured a group of reapers along with Tessa and interrogated them in Stairway to Heaven. Suffering from grief over the souls that were stuck in the Veil due to Metatron's spell, Tessa committed suicide using the First Blade while Dean was holding it. Dean was momentarily shocked by this, while the angels began to dislike him, blaming him for the reaper's death.
Dean was responsible for releasing The Darkness, after having the Mark of Cain removed from his arm. When The Darkness manifested, Dean was the first person she spoke to. He was also spared from the Rabid infection that struck a nearby town when The Darkness was unleashed.
Knowing he had to get rid of her, Dean and Sam hunted her down at Crowley's lair in Our Little World, but found he could not go through with it. Amara claimed that the two of them would always help each other. He was surprised when Amara rescued him from Crowley and ordered the demon to give Dean safe passage back. Castiel later informed Dean that The Darkness was God's sister, and he used this as an excuse for why he failed to kill her.
In O Brother, Where Art Thou?, after getting distracted by a case he and Sam believed was caused by The Darkness, Dean spotted Amara in a park, who then took him away to some place private. Dean berated Amara for taking innocent lives, but Amara pointed out that she did not kill them, but consumed them, and wished for Dean to be a part of that, to experience eternal bliss, as she claimed he does whenever they're together.
Amara kisses Dean, who initially returns it before pulling away, awestruck. Amara tells Dean that they're bonded, and that Dean releasing her was no accident, but destiny. When the angels interrupt their meeting, Amara reluctantly sends Dean away.
Dean gradually becomes distraught over his apparent connection to Amara, and reveals to Sam in Love Hurts that he does not think he can truly resist her, and therefore he is incapable of harming her. In the same episode, a Qareen takes the form of Amara, believing her to be Dean's darkest desire.
Dean and Amara meet again in Hell's Angel, when a plan to expel Lucifer from Castiel's vessel fails and Lucifer begins torturing him and Sam. Amara arrives and frees the Winchesters. Miraculously, Dean shows greater concern for Castiel than interest in Amara, which causes Amara to look momentarily upset, before she kidnaps Castiel, along with Lucifer.
Amara continues to hold Dean as someone special, as shown when Dean was immune to her fog while everyone else gets infected. According to one of the victims, The Darkness plans for the two of them to be all there is left of the world. Even Sam, in his infected state, believes Dean to favor Amara.
In hopes that Lucifer can help them defeat Amara, Dean forms a plan to rescue him. Dean distracts Amara by meeting with her in a forest. He admits he cannot resist her, and it scares him. Amara encourages him to let go, but realizes God has hidden his thoughts from her, leading her to feel betrayed.
This act seemingly causes Amara to disregard Dean, as during the battle in We Happy Few, she knocks Dean aside when he attempts to stop her from hurting God. Notably, Dean was shown trying to approach her when she arrived at his location, broken and battered, but Sam stopped him. While plotting how to defeat Amara, Dean is also shown to be reluctant to harm her which both God and Sam note.
In Alpha and Omega, with no other way to save the Universe, Dean agrees to sacrifice himself to kill Amara with a Soul Bomb despite his reservations towards harming her. After God sends him to the park where Amara is located, Dean finds her questioning her actions and instead of killing her, uses her doubts to try to convince her that her conflict with God doesn't have to end the way she intends it. Dean helps Amara to see that revenge just isn't worth it and that all she really wants is her brother back. Dean also suggests that Amara's attraction to him comes out of loneliness and what she really wants is God. Listening to Dean, Amara brings God to their location and finally reconciles with her brother before healing him, ending the situation non-violently.
|“|| Dean : Now you might be a -- an all-powerful being... but I think you're human where it counts. You simply need your brother. |
Amara : Just stop.
Dean : You don't want to be alone. Not really. I mean, hell. Maybe that's why you wanted me. But deep down, you didn't really want me... 'cause I'm not him.
— Dean to The Darkness
in Alpha and Omega
Following her reconciliation with God, Amara departs the Earth with him but not before telling Dean that Dean had given her what she'd truly wanted all along so she would return the favor for him. Awhile later, Dean finds that Amara resurrected his mother to repay his actions.
Dean first meets the angel when he's posing as his boss after manipulating Dean's memory to show Dean that he belongs as a hunter. While Zachariah helps Dean see this, Dean is angry at his way of doing it and threatens to stab him in the face.
When Zachariah later transports Dean to the Green Room to keep him from preventing Sam from killing Lilith, he tries to accommodate Dean by giving his favorite food and drinks. Dean was sickened to hear that the angels wanted the Apocalypse to start so Michael will defeat Lucifer. Dean considered smashing a statue bust over his head after learning this, despite Zachariah warning him of the ineffectiveness of the action and is enraged by the angels' true plans. Dean was freed from Zachariah's grasp when Castiel rebelled by banishing him long enough for Dean to try and reach Sam but to no avail as Lucifer was freed.
After the Apocalypse starts, Dean is especially angry to see Zachariah again given Castiel's death and them keeping him from stopping Lucifer's liberation, he refuses to side with them. Out of revenge for his manipulations, he gleefully banishes Zachariah and his followers. They meet again at the storage unit and Zachariah reveals that Dean is Michael's true vessel and he needs to lead them against Lucifer. Dean was shocked to hear this but refuses to say "yes" after realizing they need his permission. He also refuses to give into Zachariah's torture, which stops after a resurrected Castiel threatens Zachariah.
Throughout Season 5, Zachariah would hunt the brothers after they are both revealed to be Michael and Lucifer's vessels. Dean is especially annoyed when Zachariah takes him to an alternate future but is saved by Castiel after returning to his time. Despite this, he is left somewhat thankful for it as Zachariah's trip taught him he's stronger with Sam than without him and returns to hunting with his brother.
When Dean is in Heaven, Zachariah relentlessly chases him and Sam and torments Dean with a bastardized version of his mother. Zachariah would take out his frustration on Dean for ruining his reputation by punching him repeatedly. He would only stopped from torturing them by Joshua's intervention on God's orders but the trip results in Dean losing his faith in everything.
After Adam is raised by Zachariah as a trap to get Dean to say "yes". Dean confronts Zachariah who tortures both Sam and Adam to coerce Dean into submitting to his demands. Seeing both his brothers in pain, Dean finally gives in as the angel had planned all along, but decides not to go through with it and let Sam down. Dean announces to Zachariah that the first condition that Michael must meet to possess him is that he has to kill Zachariah and then takes great glee in taunting Zachariah at how unimportant he is now. Dean uses the opportunity to taunt Zachariah into getting right in his face before finally killing him with an angel blade moments after announcing his intention to kill Zachariah himself. This forever gets rid of the relentless angel's hunt for Dean.
In 2019, Dean is shocked to see Zachariah alive in the alternate timeline created by Dean inadvertently using the Baozhu to bring his father forward in time from 2003. Dean doesn't interact with Zachariah much as Dean faces off with the alternate Castiel while Sam faces and kills the alternate Zachariah. However, before he is killed, Zachariah orders Castiel to kill Sam and Dean, something that he nearly succeeds in doing.
Dean and John - Dean and John's Relationship.
Dean and Mary - Dean and Mary's Relationship.
Dean and Sam - Dean and Sam's Relationship.
Dean and Adam - Dean and Adam's Relationship.
Dean and Castiel - Dean and Castiel's Relationship.
Dean and Bobby - Dean and Bobby's Relationship.
Dean and Crowley - Dean and Crowley's Relationship.
Dean and Jody - Dean and Jody's Relationship.
Dean and Charlie - Dean and Charlie's Relationship.
Dean and Ellen - Dean and Ellen's Relationship.
Dean and Jo - Dean and Jo's Relationship.
Dean and Jack - Dean and Jack's Relationship.
Dean and Gabriel - Dean and Gabriel's Relationship.
Dean and Death - Dean and Death's Relationship.
Dean and Lisa - Dean and Lisa's Relationship.
Dean and Ruby - Dean and Ruby's Relationship.
Dean and Bela - Dean and Bela's Relationship.
Dean and Lucifer - Dean and Lucifer's Relationship
- Notably, Dean is responsible for the deaths of half the people listed here.
- In Blood Brother, Sam tells Dean that Dean doesn't have any friends because all of them are dead.