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