Dean's Relationships

This page is comprised of Dean Winchester's relationships over the years.

Anna Milton
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. They are on friendly terms until Anna goes back in time to kill Mary and John. When she does that they are enemies. Dean later witnesses her death at the hands of Michael.

Cassie Robinson
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, although Dean soon left town again.

Carmen Porter
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
Dying from an inoperable brain tumour, 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' healings before Layla was cured. Had their situations been different, there was a chance of a relationship between the two.

Abaddon
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.

Alastair
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.

Arthur Ketch
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 motorbike. 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.

Azazel
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.

Benjamin Braeden
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. Dean eventually 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
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. Together, they begin to fight their way out. Upon reaching the portal out, Dean keeps his 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 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.

Cain
Dean first meets Cain while hunting for the First Blade and is disgruntled by the demon's unwillingness to help at first. Dean is 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.

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's prediction of what is to come for Dean rattles him and after defeating Cain, Dean asks if Cain 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
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.

Emma
"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. Once Emma turned sixteen, she was assigned with the task of killing her father. 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.

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
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.

God
For most of his life, Dean lacked faith in God, 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 continued to lack faith as he didn't believe he was worthy of saving and couldn't understand why God would do it. 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 nervous while speaking to 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 mixing him up with his own father as the latter looked at with a sad expression. When God steps out as Sam and Dean talk about a plan, 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 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 finally accepts 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.

Gordon Walker
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.

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 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.

Lucifer
Dean originally believed Lucifer to be a fairy tale until Castiel told him otherwise. Dean met Lucifer for the first time when Zachariah transported him to an alternate future in the year 2014. This Lucifer possessed Sam which horrified Dean as Lucifer casually greeted him. He chose to spare Dean, right after killing Dean's future counterpart. Lucifer attempted to get Dean to understand him, but Dean bit back saying that he was like every other monster Dean hunted, the only difference being the size of his ego. Lucifer ended their conversation with assuring Dean that they would "always end up here". In the present, Dean sought to kill Lucifer by using the Colt, though the plan failed and Dean was left with relying on Sam's own plan of saying "yes" to Lucifer in order to send Lucifer back to his Cage. Dean watched as Lucifer abandoned his previous vessel for Sam, and then took Sam for his own.

At Stull Cemetery, Dean interrupted Lucifer's battle with Michael. In retaliation, Lucifer beat Dean up, calling him "a pain in my ass". Dean called to Sam as he was attacked and Sam eventually managed to take control of his body, and return Lucifer to his prison. A recently resurrected Castiel then healed Dean of his blood-soaked injuries.

Dean did not meet Lucifer again until about five years later, when Sam convinced him to allow him to speak to Lucifer. Unfortunately, Lucifer had set up a plan to escape the Cage, and despite Dean's efforts to stop him, Lucifer got out. Dean would not known of this for a time, and conversed with Castiel, unaware that Lucifer was possessing said friend. When Dean did find out, he made an effort to rescue Castiel.

Lucifer repeatedly mocked Dean over his concern for Castiel. Originally, he planned on using Dean's connection to Amara for good use, but after discovering, and subsequently obtaining a Hand of God thanks to the brothers, he ultimately chose to be rid of Dean and Sam. His effort to kill the brothers failed when Amara herself kidnapped him, an incident which he blamed the brothers for. Later on, Dean arranged a rescue mission to retrieve Lucifer, believing him to be a necessity in the war against Amara.

Once the archangel was at the Bunker, however, he began throwing a teenage tantrum at his father, forcing Dean (and Sam) to get the two to sit down and talk. Afterwards, Dean and Lucifer worked together to fight Amara, though they continued to annoy each other. Amara eventually expelled Lucifer from Castiel's vessel, much to Dean's delight, as it returned Castiel to him. However, Dean was shown to still worry about Lucifer enough to check on him when he thought Lucifer was still inside Castiel, and asked what happened to him after his eviction.

After God and Amara's reconciliation and departure, as well as after the confrontation with Toni Bevell, Dean learned from Castiel that Lucifer was still out and about and Castiel planned to capture him, something Dean offered to help with. Eventually, Castiel accepted his help and Dean traveled to Los Angeles to interrupt a concert Lucifer was hosting. Dean succeeded in chasing the guests out with gun shots fired at the ceiling. Lucifer was obviously unhappy about this, and he and Dean, Sam and Castiel got into a brief struggle, in which Dean handcuffed Lucifer.

Lucifer greeted him with mild surprise and threw him off the stage and melted the handcuffs from his wrist. Dean then bore witness to Lucifer's confession and why he was motivated to kill people randomly. Dean showed no remorse over Lucifer's sense of betrayal caused by his father's abandonment, and merely looked on in dislike as Lucifer vowed to destroy the humans in retaliation. Dean taunted Lucifer about the deterioration of his vessel, to which Lucifer agreed that Vince Vincente was wearing thin, and promptly left the vessel. Dean vowed to capture him.

Dean and Sam followed Lucifer to a church and then towards the President of the United States, who was Lucifer's next choice for a vessel. When Castiel sensed the conception of Lucifer's child, Dean remarked how he didn't know the archangel was dating. Dean later accepted help from Arthur Ketch and used his equipment to free the President from possession and send Lucifer back to Hell. Both and Sam expressed joy at finally defeating Lucifer.

Months later, Dean finds out that Lucifer had not been returned to the Cage due to Crowley's personal intervention, which has allowed Lucifer to escape a much weaker confinement. Dean angrily confronts Crowley about this, but agrees to work with Crowley again in defeating Lucifer, who is now in search of his unborn son. Dean, Sam and Castiel confront Lucifer outside Kelly's cabin, and plan to lure him and trap him inside a portal opened up by Lucifer's son. Once Lucifer is inside, Dean acts as a distraction by firing numerous bullets into Lucifer while Sam and Crowley finish the spell to close the portal.

Lucifer is unharmed, and while the spell gets completed, Lucifer is still able to escape the portal and kill Castiel right before Dean's eyes. Dean then witnesses his mother and Lucifer fall back into the portal during a scuffle between the two. The portal closes behind them, leaving Dean with a dead Castiel. Dean is quick to convince himself that Lucifer has murdered his mother and initially treats Jack with disdain since he is Lucifer's son. He assists both Sam and the resurrected Castiel in convincing Jack to choose them over his father which they succeed. He also learns from Jack that Lucifer has not killed Mary though unaware that Lucifer himself has returned.

In Devil's Bargain, Dean was shocked to hear from Castiel that an Alternate Kevin used a spell that allowed Lucifer to return. When confronting Lucifer, Dean was angry to see him again and made it clear that he will kill the latter in time but needed to get Jack and Mary away from the Alternate Michael who wants to invade their world. However, Anael aided Lucifer who began torturing Dean, Sam and Castiel but Arthur Ketch intervened and Lucifer retreated.

Michael
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. 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, Michael 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 as a vessel instead.

Dean wished to apologize to Adam, 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 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. However, he 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.

Metatron
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.

Rowena MacLeod
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. Rowena then cured Dean of the curse, with Dean not remembering a single moment of his time while under the curse.

Samuel Campbell
Samuel is Dean's maternal grandfather. They first meet in In The Beginning when Castiel send's Dean back in time. Samuel gives Dean a test to prove whether or not Dean is a real hunter. Later on Dean tells "Samuel" that he is Samuel's grandson, unaware that he was being possessed at the time.

Samuel later returns in season 6 and Dean is surprised to see 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. 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. Dean tells Samuel the next time he see him, Dean will be there to kill Samuel, which he does try but Sam stops him. Dean is never able to finish Samuel off though, since Sam is the one to kill Samuel.

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.

Dean would not remember this encounter after he woke up. It wasn't until two years later in Death Takes A Holidaythat 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 proceeded to rescue her from Alastair.

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.

The Darkness/Amara
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.

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.

Zachariah
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, Dean considers smashing a statue bust over his head despite the ineffectiveness of the action and is enraged by the angels' true plans.

After the Apocalypse starts, Dean is especially angry to see Zachariah given Castiel's death and gleefully banishes the angel and his followers. He later refuses to give into Zachariah's torture and is annoyed by Zachariah taking him to the future. Despite this, he is left somewhat thankful for it as Zachariah's trip taught him he's stronger with Sam than without 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 is only stopped from torturing Sam and Dean 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 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.

Also Checkout
Dean and Bela - Dean and Bela's Relationship

Dean and Castiel - Dean and Castiel's Relationship

Dean and Charlie - Dean and Charlie's Relationship.

Dean and Ellen - Dean and Ellen's Relationship

Dean and Jack - Dean and Jack's Relationship

Dean and Jo - Dean and Jo's Relationship

Dean and John - Dean and John's Relationship.

Dean and Lisa - Dean and Lisa's Relationship

Dean and Mary - Dean and Mary's Relationship

Dean and Ruby - Dean and Ruby's Relationship.

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.