Editing Dean's Relationships

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|tab1 = Overview
|tab2 = Synopsis
|tab3 = Abilities and Weaknesses
|tab4 = [[Killed by Dean Winchester|Major Kills]]
|tab5 = [[Dean's Relationships|Relationships]]
|tab6 = Quotes
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This page is comprised of Dean Winchester's relationships over the years.

==Romantic relationships==
===[[Anna Milton]]===
[[File:Snmain111908.jpg|thumb|left]]
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 be born. Dean later witnesses her death at the hands of Michael.

===[[Cassie Robinson]]===
[[Image:Dean and Cassie.jpg|thumb|200px]]
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.

===[[Carmen Porter]]===
[[File:Carmen.jpg|thumb|left]]
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.

===[[Layla Rourke]]===
[[Image:Dean and Layla.jpg|thumb|166px]]
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.

===[[Robin (Bad Boys)|Robin]]===
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 [[Hunter|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.[[File:Bad Boys 01.jpg|left|thumb|206x206px]]Dean promised to take her to the homecoming dance, though [[John Winchester|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.
[[File:Dean and LIsa.webp|thumb|247x247px]]
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.

=== [[Lisa Braeden|Lisa]] ===
'''[[Dean Winchester]]''' and '''[[Lisa Braeden]]''' have shared a complicated, romantic relationship. They're almost like family, which includes Lisa's son [[Ben Braeden|Ben]], due to Dean's relationship with the two. Dean deeply cares for Lisa and Ben and would hate to see them hurt. On multiple occasions, Dean has shown that - of all the women he has slept with - he truly loves Lisa. Before and during the first few episodes of, season 6, Dean lives with the Braedens for a full year, He has a monogamous relationship with Lisa and takes on a paternal role with Ben.

==Other relationships==
===[[Azazel]]===
[[File:Azazel telling Dean that he killed his son Tom 1.PNG|thumb|288px|Azazel possessing Dean's father.]]
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.

===[[Alastair]]===
[[File:AlDeanPayback2.jpg|thumb|left|288px|Dean tortures Alastair.]]
Dean met Alastair after he was dragged off to Hell by a [[Hellhounds|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 [[Alastair's first vessel|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 [[Tessa|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.

===[[Abaddon]]===
[[File:AbaddonDeath.jpg|thumb|275px|Dean kills Abaddon with the First Blade.]]
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 [[Henry Winchester|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 [[Battle of the Humboldt Hotel|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.

===[[Arthur Ketch]]===
[[File:Bring 'em Back Alive 13.jpeg|thumb|left|220x220px|Arthur and Dean working together to save Mary and Jack]]
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 Ketch's motorcycle|Arthur's motorcycle]]. Due to Dean's conflict with [[Lady Toni Bevell|Toni]], who is a co-worker of Arthur, [[Mamma Mia|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 Winchester|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 Ketch's motorcycle|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.

[[War of the Worlds|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.

[[Devil's Bargain|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 [[Mary Winchester|their mother]] and [[Jack Kline (Nephilim)|Jack]] back. His decision shocked Arthur who silently accepts.

As the Winchesters prepare to [[Portal Creation|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 [[Bounty Hunter (Bring 'em Back Alive)|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 [[Murder of Charlie Bradbury|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 [[Arthur and Charlie's Captors|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.

In ''[[Stranger in a Strange Land]]'', Arthur is shown to care for Dean enough to search for the [[Hyperbolic pulse generator]] to expel Michael from him but failed.

In ''[[Jack in the Box]]'', Dean appears to have lost all disgust towards Ketch's attraction to Mary, as he invited him to come to her funeral and didn't hold it against him for not coming and drank the scotch he gave him.

In ''[[Raising Hell]]'', Dean is forced to shoot Ketch to free him from Francis's possession and apologized for it but humored him when Ketch stated Dean wanted to kill him again and told him to take care. Unfortunately, Dean's refusal to have Arthur kill Belphegor turns disasterous as Ardat, Arthur's hirer, kills him. Dean is clearly upset by his death.

===[[Benjamin Braeden]]===
[[File:Dean and Ben.jpg|thumb|Ben and Dean.|187x187px]]
Dean is like a father to [[Benjamin Braeden|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.

===[[Benny Lafitte]]===
[[File:DeanBenny-600x337.jpg|thumb|left|322px|Dean and Benny in Purgatory.]]
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.

In ''[[Mamma Mia]]'', [[Lady Toni Bevell]] attempts to question Dean about his relationship with Benny. Dean is obviously startled to have Benny brought up again but doesn't answer her questions.

Upon returning to Purgatory, Dean finally learns that Benny has been killed by his own kind for his actions and was devastated by his friend's death, stating how he couldn't even repay the debt he owed to Benny for saving his and Sam's life.

===[[Cain]]===
{{Quote|Dean: Tell me, I don't have to do this! Tell me you can stop!<br>
Cain: I will never stop.
|Dean's last conversation with Cain|The Executioner's Song}}
[[File:The Executioner's Song 08.jpg|thumb|222px|Cain and Dean fight to the death.]]
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 [[Hunt for the First Blade|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 learned that Cain was the one who trained the Knights of Hell, Abaddon included as well the fact that he wiped out the order.

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 [[Colette Mullen|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.

===[[Dick Roman]]===
[[File:Threat.jpg|thumb|left|220x220px|Dean threatens Dick]]
Dean first meets the [[Leviathans|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 [[Bone Of Righteous Mortal Washed In the Three Bloods of Fallen|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.

===[[Emma]]===
{{Quote|Please don't let him hurt me.|Emma's last words to Dean}}[[File:713AmazonGirlDean.jpg|thumb|Dean and his daughter.]]
Dean's only known biological child is an [[Amazons|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.

===[[Gadreel]]===
[[File:DeanGadreel.jpg|thumb|left|220x220px]]
Dean first meets Gadreel when he prays for help to save Sam and the angel comes to answer his prayer. Dean kills [[Rogue Angel|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 [[Resurrection|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 [[Angel Suppressing Sigil|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 Tran|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 after realizing he wanted death and resolved to leave him to rot. However, Dean reluctantly trades him for Castiel to Metatron.

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.

===[[Garth Fitzgerald IV]]===
[[File:708.jpg|thumb|Dean and Garth]]
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.

In ''[[Nightmare Logic]]'', Dean calls Garth to warn him of [[Michael (Apocalypse World)|Michael's]] enhanced [[monsters]] and traps for hunters.

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.

===[[God]]===
{{Quote|[[Mary Winchester|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!|[[Dean]] to [[God]]|''[[Moriah]]''}}
[[File:Dean and God at the park (All In The Family).PNG|thumb|left|Dean talks to God]]
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 [[Houses of the Holy|the freak death]] of a human criminal seemed like "an act of God." After [[Castiel]] [[resurrection|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 "[[Sam|my brother]] in [[Lucifer's Cage|a hole]]."

As Chuck Shurley, Dean was at first aggressive towards God before he was revealed as a [[Prophet]] and at first disbelieving about [[Supernatural (books)|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 [[ghosts|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 [[John|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 [[healing|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.

After seeing God again in ''[[The Trap]]'', Dean immediately punches him in the face even though it has little effect. Dean comments that God knew he had to do that which God acknowledges before punching Dean back, sending him flying across the room.

During ''[[The Gamblers]]'', Dean and Sam decided to undo the curse God put on them and went up against the goddess of luck [[Fortuna]]. They told her they plan to take the fight to God or go out trying, something that caused her to restore their luck.

Dean was surprised when Billie later revealed that God's book in [[Death's Reading Room]] reveals that Jack is the one who ultimately kills God. It also turns out that Dean and Sam will have role in this as well.<ref name="Galaxy Brain">''[[Galaxy Brain]]''</ref>

===[[Gordon Walker]]===
[[File:Supernatural-hunted 1247751047.jpg|thumb]]
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 Winchester]]===
[[File:As Time Goes By 03.jpg|thumb|left|250px|Dean and Henry]]
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 [[Winchester Family|Winchesters]] and brawny [[Campbell Family|Campbells]] together to produce them.

Through Henry, Dean and Sam learn about the [[Men of Letters]] and found a new home in the [[Men of Letters bunker]].

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.

===[[Kevin Tran]]===

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 [[Linda Tran|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 Fitzgerald IV|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|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 [[Gadreel|the angel]] possessing Sam is not [[Ezekiel]] and turns to Kevin for help in [[Angel Suppressing Sigil|suppressing the angel]] so Sam can expel him. Dean can only watch, horrified, as Gadreel [[Smiting|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 [[Linda Tran|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 [[Kevin Tran (Apocalypse World)|Alternate Kevin]] used a spell that allowed Lucifer to return and that the latter worked for [[Michael (Apocalypse World)|Alternate Michael]] who wants to invade their world.

In ''[[Raising Hell]]'', they meet again where the latter rescued Dean from violent ghosts. Dean was surprised at the reunion but horrified to learn Kevin was sent to Hell. Kevin helped in detaining the ghosts and Dean promised to help him go to Heaven. However, [[Belphegor]] informs them that a soul cannot enter Heaven once going to Hell. Kevin assured Dean that he'll be fine wandering, rather than go to Hell again.


===[[Lilith]]===
[[File:Proverbs 17 3 05.jpg|thumb|Dean unknowningly reunites with Lilith]]
Dean first heard of her from [[Bela Talbot]] and was made aware that she holds his deal.

During ''[[No Rest for the Wicked]]'', Dean sought to kill her, to prevent his soul from going to Hell as per his deal. Despite his efforts, he failed and Lilith commanded a [[hellhound]] to kill Dean. Due to her, Dean was ultimately sent to forty years of torture (due to Hell's time flow).

Dean was resurrected by Castiel, though became on stopping Lilith because of her breaking the [[66 Seals]] to release Lucifer.

In ''[[The Monster at the End of This Book]]'', Dean heard she resurfaced and tries to bargain with Sam on not facing her but he was intent. Dean was forced to pray to Castiel who supplied him with a method of stopping Lilith. Dean brought Chuck Shurley and she retreated, since Chuck was protected by an Archangel.

In ''[[Lucifer Rising]]'', Dean learns the angels want her to succeed in freeing Lucifer. After Castiel rebelled, he told Dean that Lilith is the last seal and killing her will ultimately trigger the Apocalypse. Dean tried to stop Sam from killing Lilith but Ruby prevented him. After Sam killed the demon, Dean was horrified to watch the release the Devil and start [[The Apocalypse]].

Dean would not hear of Lilith for a decade, until she is resurrected in ''[[Proverbs 17:3]]''. Lilith masqueraded as a helpless woman who was attacked by werewolves and deceived Dean. Lilith also brings up on how she was suppose to seduce him, realizing that won't happen now and he confirmed it. She soon revealed God resurrected her to steal [[The Equalizer]]. Dean refused her demands and attempting to attack her with an [[Angel Blades]] but she easily repelled him. Lilith soon threatened Sam which was more than enough to get Dean to comply. While he was getting the gun ready she remarked on how she should've focused on him rather than Sam the While he was getting the gun ready she remarked on how she should've focused on him rather than Sam the first time. However, Dean's compliance was a lie and Lilith begins [[biokinesis|inflicting]] wounds on him, threatening to cause a death by a thousand cuts. Dean was saved when Sam arrived and shot Lilith in the head with a [[devil's trap bullets|devil's trap bullet]], immobilizing her, but Lilith [[terrakinesis|causes the ground to shake]] and pushes the bullet out of her head with [[telekinesis]]. Intercepting the Winchesters outside, Lilith correctly predicts that they have kept the gun in [[The Impala]] and retrieves it from the glove compartment. Lilith [[thermokinesis|causes the gun to melt]] and vanishes after promising to see them again. However, they never saw each other again as Michael [[Standoff at Jaci's Red Wagon|later killed]] Lilith.

===[[Michael]]===
[[File:Michael talks to dean.jpg|thumb|left|250px|Michael talks to Dean]]
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.

During ''[[Back and to the Future]]'', Dean learns from [[Belphegor]] that God opened all gates to Hell, including the Cage. Dean expressed worry at the Archangel likely coming after him and Sam for [[revenge]] but didn't seem relieved to hear Michael is sitting idle.

In ''[[Our Father, Who Aren't in Heaven]]'', Dean is the most adamant about seeking out Michael's help when they learn that he might know something that can help defeat God. While God and Lucifer claimed Michael to be insane, Dean believes that they were simply lying and is proven right. Michael isn't pleased to see Dean again, angry that Dean abandoned Adam in the Cage while letting Lucifer free upon the world. He also empathizes with Michael after Castiel showed him the truth, thinking that the angel exaggerated by doing that. However, after realizing the truth, Michael becomes more cooperative and provides Dean and Castiel with the spell they need to trap God and the [[rift]] they need to [[Purgatory]]. Dean then releases Michael from the [[Supernatural Handcuffs]], letting the archangel go despite his refusal to help them out anymore. On Dean's request, Michael relinquishes control to Adam so that Dean can apologize to his younger brother.

In ''[[Despair]]'', Dean is annoyed that Michael isn't returning their prayers to him.

[[File:Inherit the Earth 01.jpg|thumb|250px|Dean talks to Michael]]
In ''[[Inherit the Earth]]'', Dean learns from Jack that Michael is still around and leads the Winchesters to a church after sensing his presence. In the church, they find Michael who expresses surprise that they survived. Michael explains that when the Rapture first began, he took refuge in the church, St. Michael's to avoid detection. Dean also learns from Michael that Adam died with the rest of humanity and wonders how the Winchesters and Jack survived. Dean explains that God thought it would hilarious to watch the three of them on an empty planet and so spared the Winchesters and Jack. Dean calls him "Daddy's boy" after he mentions trying to honor his father's name. Dean also reminds him that they reached out to Michael only to have the archangel ignore them. Michael promised to help this time stating"That was then, this is now. Tell me what you need me to do." 

The Winchesters lead Michael back to the bunker where they unveil [[Chuck's Death Book]] for the archangel. Dean thought Michael could open the God's death book, so they could know how to defeat him. However, even Michael can't get the book open. Both Dean and Michael are wary about the [[resurrection|resurrected]] [[Lucifer]] siding with them. Michael even questioned if the Winchesters are seriously thinking about trusting his brother. Dean replied that they aren't exactly trusting Lucifer. 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 later speaks to Michael on his condition and Michael admits that he's a bit winded, having not been in a battle like that in several centuries. Dean tells Michael that he's glad that Michael was there and that Chuck is getting desperate, knowing that something is up and wouldn't take the chance of showing up personally. Michael acknowledges this and is stunned that his father resurrected Lucifer and didn't even reach out to him. Dean questions if Michael wanted Chuck to reach out to him and Michael insists that he didn't and that Chuck obviously knows the Death book could be lethal to him, but its useless without Death to read it. Dean tells Michael that its at least open now and Sam recognized some of the symbols and writing as being some form of Enochian. As such, Sam is going to try to use the ''[[Book of the Damned (object)|Book of the Damned]]'' to try to translate Chuck's Death Book and figure out the End.

Later, Michael enters the library where Dean and Jack are researching with a book and asks if Sam is making any progress. Dean tells Michael that he hopes so since Sam has been busy for a long time and Sam enters. Sam tells the group that he thinks he was able to piece together the spell from the book that can help them which must be done in a particular place at an exact angle from the sun and it will release an unstoppable force that will find Chuck and finish him. The group travels to the location at a lakeside where Sam performs the spell, sending blue light into the sky that then vanishes. As the Winchesters wonder what went wrong, Chuck appears behind the group and tosses Sam, Dean and Jack aside with telekinesis. It is made clear that Michael has betrayed them, when he and God greet each other and Chuck thanks Michael for the heads-up about the Winchesters' plans. However, Michael's actions lead to his death after God brought up that the Archangel had sided with the Winchesters before and Chuck can't forgive that. Dean was stunned to watch God destroy Michael. After rendering God powerless, the Winchesters reveal that they anticipated Michael's betrayal and came up with a plan to use Michael to get at God after noting on how angry Michael was at God using Lucifer to get to the book. Dean states they used Michael's desperation to be "Daddy's boy" against him. In addition, the original plan to turn Jack into a bomb to kill Chuck had actually turned Jack into a of power vacuum. They state when Michael and Lucifer fought and Michael killed Lucifer, Jack absorbed the power coming off of them and was charged up greatly as a result. In addition, Jack absorbed the power given off by Michael's death which, combined with the power given off by God beating on the Winchesters, made Jack unstoppable and capable of taking God's power from him.

In the end, Dean indirectly acted on his previous promise to get rid of Michael that he made at the [[Stull Cemetery]]. 

==== Dean and [[Michael (Apocalypse World)|Alternate Michael]]====
[[File:Dean vs Michael.jpg|thumb|Dean faces Alternate Michael]]
During ''[[Devil's Bargain]]'', Dean has learned from Castiel that an [[Michael (Apocalypse World)|Alternate Michael]] is coming to invade his world and was shocked to hear that his mother [[Mary Winchester]] and [[Jack Kline (Nephilim)|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 Kline (Nephilim)|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 [[Power Granting|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 [[Kaia Nieves (The Bad Place)|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.

During ''[[Lebanon]]'', he attempts to use a [[Baozhu|magic treasure]] to evacuate Michael but it has [[John Winchester|another route]].

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.

===[[Mick Davies]]===
[[File:Ladies Drink Free 05.jpg|thumb|left|Dean and Mick]]
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 Kline (Nephilim)|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 [[There's Something About Mary|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 and saddened about Mick's death, having thought him alive and in London as told by [[Arthur Ketch]]. Dean later on openly admitted that Mick's death was part of the reason why he wanted Ketch dead, showing that Mick was, up until Arthur's own redemption, the only British Men of Letters Dean truly cared for.

===[[Metatron]]===
[[File:SPN 1357.jpg|thumb|220px|Dean and Metatron.]]
Upon first hearing of Metatron, Sam 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 Angels|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 [[Homeless Angel|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-[[Humans|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 of Lucifer|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.

===[[Rowena MacLeod]]===
[[File:Regarding Dean 07.jpg|thumb|left|Dean and Rowena]]
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 [[Loughlin Family|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.''

When Rowena died, Dean was absolutely devastated, showing that like Sam, he came to care a lot for her, and he even went as far as to blame Castiel for it as it was Castiel killing Belphegor and destroying the Crook that forced her to do it.

===[[Samuel Campbell]]===
[[File:Supernatural(22).jpg|thumb|200px|Dean and his grandfather Samuel]]
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 [[Vampires|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 declares that he will get free and tells his grandfather the next time he sees him, he'll be there to kill Samuel, something that left Samuel shaken.

In [[...And Then There Were None]], Dean sees Samuel and 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 Samuel 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 apologize. 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.

===[[Tessa]]===
[[File:Dean and Tessa3.jpg|thumb|left|Dean and Tessa]]
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 [[The Apocalypse|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, appeared and 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]]''. She was upset and insulted Dean to Sam. Later, Dean remarked he liked her, and they have history. Tessa momentarily calmed down to talk but explained she was suffering from grief over the souls that were stuck in the Veil due to Metatron's spell. Dean wanted to know about more suicide-bombers, drawing out the First Blade and she realized [[Mark of Cain|its meaning]]. After agreeing on the mutual standing of no choice, Tessa committed suicide using the First Blade while Dean was holding it. Before dying, she thanked Dean for ending her pain while he was momentarily shocked by this, while the angels began to dislike him, blaming him for the reaper's death.

===[[The Darkness|The Darkness/Amara]]===
[[File:Dean and Amara relationship 1.png|thumb|238x238px]]
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 [[The Darkness' Fog|her fog]] while everyone else gets infected. According to [[Jan Harris|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 [[Rescue of Lucifer|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.

{{Quote|'''Dean :''' Now you might be a -- an all-powerful being... but I think you're human where it counts. You simply need your brother. <br>'''Amara :''' Just stop. <br>'''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|''[[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 [[resurrection|resurrected]] [[Mary Winchester|his mother]] to repay his actions.

In ''[[Destiny's Child]]'', Dean believes that due to the balance being off after Jack kills God, he should kill Amara.

In ''[[Gimme Shelter]]'', Dean confronts Amara over the resurrection of his mother and though he manipulates Amara to help them, he is visibly conflicted.

In ''[[Unity]]'', Amara reminds Dean how she told him that they would always help each other when they first met. Later, Chuck comments on their weird relationship. Amara asks if it had been Chuck's writing, but he shows disgust at the very idea. Amara is left utterly heartbroken at Dean's betrayal of her, having truly cared about him and wanting Dean to care about her in return.

===[[Zachariah]]===
[[File:ZachariahDean.jpg|thumb|left|233x244px|Zachariah tortures Dean.]]
Dean first meets the [[angel]] when he's posing as his boss after [[Memory Manipulation|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, women, 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|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 [[angel banishing sigil|banishes]] Zachariah and [[Zachariah's Foot-Soldiers|his followers]]. They meet again at the storage unit, where 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 Timeline (The End)|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 [[Mary Winchester|his mother]]. Zachariah would take out his frustration on Dean for ruining his reputation by punching him repeatedly. He would only stop 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 [[Raising of Adam Milligan|raised by Zachariah]] as a trap to get Dean to say "[[yes]]".  Initially, Dean was going to say yes but the actions of his friends change his mind When he confronts Zachariah, the latter 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 [[possession|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 [[Skirmish at Big & Little Palace|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.

== Minor Sexual Relationships ==

===== [[Tara Benchley]] - ''[[Hollywood Babylon]]'' =====
On Sam and Dean's case to find ghosts killing people on Stage 9 in a Hollywood horror movie, Sam tells Dean that an actress named Tara Benchley is in the movie which prompts him to pay attention to their conversation. It is then realized that this is one of his celebrity crushes from previous movies he has watched.

==Meaningful Relationships==
[[Dean and John]] - Dean and John's Relationship.<br />
[[Dean and Mary]] - Dean and Mary's Relationship.<br />
[[Sam and Dean|Dean and Sam]] - Dean and Sam's Relationship.<br />
[[The Winchesters and Adam|Dean and Adam]] - Dean and Adam's Relationship.<br />
[[The Winchesters and Claire Novak|Dean and Claire]] - Dean and Claire's Relationship.<br />
[[Dean and Castiel]] - Dean and Castiel's Relationship.<br />
[[Dean and Bobby]] - Dean and Bobby's Relationship.<br />
[[Dean and Crowley]] - Dean and Crowley's Relationship.<br />
[[Dean and Jack]] - Dean and Jack's Relationship.<br />
[[The Winchesters and Jody Mills|Dean and Jody]] - Dean and Jody's Relationship.<br />
[[Dean and Charlie]] - Dean and Charlie's Relationship.<br />
[[Dean and Ellen]] - Dean and Ellen's Relationship.<br />
[[Dean and Jo]] - Dean and Jo's Relationship.<br />
[[The Winchesters and Gabriel|Dean and Gabriel]] - Dean and Gabriel's Relationship.<br />
[[Dean and Death]] - Dean and Death's Relationship.<br />
[[Dean and Lisa]] - Dean and Lisa's Relationship.<br />
[[Dean and Ruby]] - Dean and Ruby's Relationship.<br />
[[The Winchesters and Bela|Dean and Bela]] - Dean and Bela's Relationship.<br />
[[Dean and Lucifer]] - Dean and Lucifer's Relationship.<br />

==Trivia==
*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.

==References==
{{Reflist}}
[[Category:Relationships]]