Dean's Relationships

This page compromises of Dean's relationships over the years.

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.

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.

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 and 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, its 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. But Ben still looks up to 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, now 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. Ben is shocked by Lisa being fatally wounded by the demon and Dean is forced to slap him to snap him out of it. Dean goes against his beliefs and lets Ben use a shotgun to hold the demons off so he can carry Lisa to safety and despite his fear, Ben seems to do good. 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 completely forgets Dean who is left devastated by the loss of him and Lisa.

Carmen Porter
In Dean's fantasy world, Carmen was his live-in girlfriend. She is essentially what he wanted at the time. She knew almost everything about him (his favorite beer and foods). She also works as a nurse and Dean is surprised he is dating a respectable woman. In the real world, she was a model in a magazine for his favorite beer.

Anna Milton
Dean meets her during the fourth season, and protects her from angels and demons. During Heaven and Hell, they have a moment together and hook up for the night. Dean protects her until the moment they 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, but both wish they could say they're glad to see each other.

Gordon Walker
Dean and Gordon meet in Season 2's Bloodlust. At first, Dean and Gordon hit it off pretty well. Even do a hunt together. But once Dean realizes how psycho Gordon is, they become enemies. Espically when Gordon begins to hunt Sam down in Hunted. In that episode Gordon takes Dean prisoner. They remain enemies till Fresh Blood, when Sam kills Gordon.

Samuel Campbell
They first meet in In The Beginning when Castiel send 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. Samuel later returns in season 6 and Dean is surprised to see him. 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 tries but Sam stops him. Dean is never able to finish Samuel off though, since Sam kills Samuel.

Michael
Dean Winchester was predestined to be 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, Michael however didn't really hate Dean, although he considered him inferior to him. 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 considers letting Michael use him, but changes his mind as he doesn't want to let Sam down. When Michael coldly tells Dean that "Adam isn't home right now" when Dean apologizes to his half-brother who Michael is using as a vessel, Dean warns him he's coming after Michael next, something Michael doesn't take seriously. As Dean is partially responsible for his imprisonment, it can be assumed that Michael now deeply hates Dean.

Crowley
Dean Winchester and Crowley were never friends, but were allies againist Lucifer. Unlike Sam, Dean is more willing to trust Crowley and the two of them work together. When the Apocalypse is averted, they become enemies with Dean threatening to kill Crowley to force him to break Bobby's deal. Even after the deal is broken Dean still wants to kill him only to be stopped by Sam. Crowley further angers Dean by kidnapping Ben and Lisa to make Dean stop chasing him. But Dean doesn't stop and continued to hunt for Crowley to stop him from opening Purgatory. This however doesn't stop Dean from working with Crowley when necessary and he makes a deal with him to reverse all of Guy's deals and one to deal with the Leviathans. However, after returning from Purgatory, Dean begins to actively try to kill or banish Crowley to Hell forever. In Sacrifice, Dean tricks and captures Crowley with Devil's Trap engraved handcuffs so Sam can turn him human and complete the third trial. After keeping Crowley captive afterwards in the Bunker, Dean turns to him for help in freeing Sam from Gadreel's control in Road Trip. Dean reluctantly agrees to give Crowley his freedom in exchange and lets him possess Sam to communicate with him. Crowley's efforts allow Sam to expel Gadreel, but while Dean is grateful and allows Crowley to go free, he warns him that he'll kill the demon the next time they meet. Despite this threat, Dean reluctantly allies himself with Crowley to take down Abaddon by locating the First Blade. Dean and Crowley hunt the Blade together, finally locating the demon Cain who is the creator of the Blade. Cain eventually gives Dean the Mark of Cain so he can wield the Blade and helps him and Crowley escape after telling him where to look: the bottom of the ocean. However, while Dean got what he needed, he is furious with Crowley as he realized Crowley used him after seeing him let Dean fight off three demons alone when he could've helped. Crowley confirms this, saying he needed Dean's help to locate Cain and to get him to help as Cain would've never helped Crowley. Disgusted with what Crowley has done, especially as it resulted in the death of hunter Tara, Dean promises to kill him once they've dealt with Abaddon, but sends him after the Blade first as for the time being, he and Crowley still need each other to stop Abaddon.

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 and sometimes while, 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.

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.

Benny
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.

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.

Also Checkout
Dean and Bela

Dean and Lisa- Dean and Lisa's Relationship

Dean and Ellen- Dean and Ellen's Relationship

Dean and Jo- Dean and Jo's Relationship

Dean and Mary - Dean and Mary's Relationship

Dean and Ruby -Dean and Ruby's Ally-Hate Relationship.

Dean and John - Dean and John's Relationship.

Dean and Charlie - Dean and Charlie's Relationship.