Dean's Relationships

Dean's Relationships he has encountered throughout his life. This includes all the friends, allies, lovers, and enemies. Also this page will host links to other relationship pages linked to Dean. This way it won't cluder Dean's main page.

Cassie Robinson


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 togther, although Dean soon left town again.

Layla Rourke
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
Benjamin Braeden Dean is like a father to Ben. At first Dean thinks Ben is his son, but Lisa tells him otherwise. Later on Dean shows Ben how to take down a bully. A couple years later, Dean comes to live with Lisa and Ben. 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. Ben no longer remembers Dean due to Castiel erasing his memories.

Andrea Barr
Andrea Barr Widowed mother of Lucas, Andrea seems immune to Dean's charms when they first meet, even shooting him down when he tries a chat-up line on her. However, by the time he and Sam leave the area, she clearly starts to realize the attraction between them, or at least seriously appreciates him saving Lucas, and kisses him on the lips.

Carmen Porter
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 nursem 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 til the moment they threaten Sam. Whenever Anna pops in, Dean is surprised to see her, but treat her kindly. They are on friendly terms until Anna goes back in time to kill Mary and John.

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 pycho 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.

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 adverted, they become enemies. 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.

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.