Sam's Relationships

Sam Winchester and his other relationships he encounters in his life. The minor friends, enemies, and lovers he has encountered.

Jessica Moore


They had been together for over a year when Dean suddenly arrived in their apartment and dragged Sam off to hunt a woman in white. When Sam got back, he discovered Jess on the ceiling in flames - exactly the same way his mother had died 22 years earlier. Even after her death, Sam still loves her, although he is finally realizing that he needs to move on.

Samuel Campbell
Samuel is Sam's grandfather. Samuel was dead up until Season 6 when Sam is also raised from Hell. The two find each other and begin hunting together. They hunt together for a whole year, and then Dean is brought into the picture. Then it is known that Sam doesn't have a soul, and Samuel admits he knew something was off with Sam. Sam though does trust Samuel, until he chooses Dean over Samuel. Samuel later gives Sam over to Crowley, who had promised to bring Mary back. When Sam got his soul back, all the memories of him and Samuel are locked away. When they meet again, Sam doesn't trust Samuel, and eventually is the one who shoots Samuel.

Meg Masters demon


The first time Sam and Meg met, they were both trying to make their way to California. He is unaware that she is actually a demon working for Azazel possessing an innocent girl to get close to him. They spent some time waiting at the bus station and got to know each other pretty well. Meg pretends to sympathize with Sam's frustration with Dean and pushes him to remain away from him, but is unsuccessful. Meg later complains to Azazel about not killing Sam and Dean which she could have easily done. The second time they met, Sam realised that something was unusual about her - just before she tried to have him and Dean killed by daevas that she was controlling. Despite her psychotic tendancies, she was very attracted to Sam and seemed to want to try and get together with him, although that was actually just a act to get close to him. When she returns and is captured, Sam performs an exorcism on the demon in order to save the real Meg Masters and is reluctant to continue after she gives up John's location as she could still be useful and exorcising the demon will kill the girl she is possessing. Sam reluctantly finishes at Dean's request and sends the demon to Hell. Though the real Meg dies, she is greatful to Sam for freeing her of the possession she had to endure for over a year. The demon returns and possesses Sam and makes it look like he is evil to try to force Dean to kill him. Eventually Bobby forces the demon to flee, but Sam is left with the knowledge of what he did while possessed. When Meg returns possessing a new body, she taunts him about his lack of power against her, but flees when Dean kills her minions. She later sics Hellhounds on them, killing Ellen and Jo and leaving Sam devastated. Sam, while soulless, later proposes an alliance with the demon against Crowley in an attempt to kill him and get his soul back. After Crowley is "killed," Sam goes to kill Meg, but she flees again. When Dean allies with Meg to protect Castiel, Sam is reluctant to trust her, but Dean tells him its more like an "enemy of my enemy" situation. Sam works with Meg to stop Kevin Tran from running off with The Word of God and is a little shocked when angels believe he is in a relationship with her. Sam's distrust of Meg goes so far that he snares her in a Devil's Trap when she returns from killing two demons, but after she explains that her goal is to kill Crowley and not to mess with them, Sam frees her and she earns his trust. This causes him to be more comfortable around Meg and even ally with her to destroy the Leviathans. After Dean returns from Purgatory, he indicates that he may have looked for her for help, but says that he doesn't know where she is. After they rescue Meg from Crowley's demons, Sam once again allies himself with her against Crowley and displays only slight distrust of her, though he and Dean also show it for Castiel. Despite this, he works with her to demon-proof the building where the angel tablet is and at her prodding confesses everything that has happened. Meg is aware of his desire to have a normal life from her possession of him and actually sympathizes with his situation with Amelia Richardson, indicating that she understands what its like to have someone you love change you due to her love for Castiel. Meg and Sam fight side-by-side against Crowley's demons and when Crowley himself shows up, Meg tells Sam to get Dean and Castiel while she holds Crowley off. Despite learning Sam and Dean's plan to seal the Gates of Hell with all demons inside, which would include her, Meg doesn't betray the trust Sam placed in her and fights Crowley who beats her badly. Her actions allow Sam, Dean and Castiel to escape and as Sam watches horrified, Crowley kills Meg.

Lori Sorensen
In Ankeny, Iowa, Sam amd Dean went to a local university to investigate the Hookman. Sam and Lori bond over both of them having lost someone important, and an attraction forms, eventually leading to a passionate kiss, but it was too soon after Jessica's death for Sam. Despite mutual attraction, and Dean offering to stay in town for a while, Sam left. However Sam would correct this mistake with his next romance with Sarah, finally moving on with Jess and staying in town.

Sarah Blake


The daughter of an auction house owner, Sarah got involved with Sam when he tried to use her to get information about a haunted painting. Before he knew it, he realised he was attracted to her but didn't want to get close in case she got hurt. She reminded him that it was her choice and she helped out on a ghost hunting mission. When Sam and Dean had to leave, Sam finally made his move and kissed her, deciding to stay in town a few days so they can be together, beginning his moving on from Jessica. Dean later suggests they go visit her again, but Sam refuses. They eventually reunite, but by then Sarah is happily married with a daughter and Sam is happy for her. Sam is devastated when Crowley kills her and considers his offer of surrendering as a result.

Madison


As soon as Madison and Sam meet, there is a clear attraction between them, but it isn't until they believe her clear of the werewolf curse that she and Sam finally sleep together. However, the devestating truth is that when Sam wakes up she is still cursed and in their final, tragic moments together, Madison begs Sam to kill her in order to prevent her from killing anyone else - something he ends up doing, no matter how much it hurts him as she is the first girl he was open to loving since Jessica died. Chuck Shurley's publisher referred to her as the first woman Sam really loved since Jessica after reading the Supernatural books.

Crowley
Sam Winchester and the demon Crowley were never friends, but one time allies against Lucifer. Due to his previous experience with Demons thanks to Ruby, Sam never really trusted Crowley, and tried to kill him many times. Sam later unknowly works for Crowley, collecting creatures for Crowley. When Sam does find out, Crowley holds Sam's soul as ransom and forces Sam to work. Eventually, Sam and Dean get fed up with doing Crowley's dirty work, so they team up with Meg and Castiel and kill him. However, it's later revealed that Crowley is still alive and Sam and Dean begin to hunt for Crowley, and stop him from opening Purgatory. In season 7, Sam reluctantly allies with Crowley at times against the Leviathans, notably when they need his blood for the weapon that can kill Leviathans. Despite this, Sam doesn't trust Crowley. After Dean kills Dick Roman and disappears with Castiel, Crowley appears and taunts Sam about being "well and truly on your own" and kidnaps Kevin Tran refusing to tell him where Dean and Castiel are. Sam works with Dean to seal up Hell and kill or forever trap Crowley in season 8 after Dean's return from Purgatory. Sam tries to turn Crowley in "Sacrifice", even saving him from Abaddon, but stops at the last moment at Dean's insistence. In season 9, Sam reluctantly works with Crowley to stop Abaddon. After Dean kills Abaddon, Sam lets Crowley go free but refuses to help him remove a devil's trap bullet, saying that letting him live should be enough for him. He gets angry when Dean works with Crowley to hunt Metatron and sends him away. In season 10, Sam yells at Crowley when he finally gets him on the phone and learns that he is sending demons after Dean. Crowley lets Sam track Dean down to force him to get moving and helps Sam capture Dean in order to stop him as Dean as a demon is completely out of control. Sam hands him the First Blade in exchange.

Amy Pond
Amy and Sam met when they were very young. Sam saves Amy from a bunch of boys, and the two connect and Sam has his first kiss. He later finds out that she is a kitsune, but lets her go since she saved his life. Years later, Sam notices similar killing happening again, and tracks Amy down. Amy tells Sam she was only killing for her son, Jacob. Knowing her, Sam lets her go, only for Dean to kill her later. Her death causes a temporary argument between Sam and Dean which later gets resolved.

Becky Rosen
Becky is a Supernatural fan and is a Sam lover. Sam doesn't have any feelings for Becky, but puts up with her when they meet. The two first meet in Sympathy for the Devil when Chuck sends Becky to deliver a message. She immediately begins touching Sam when she first meets him and Sam is extremely uncomfortable. Becky continues to hit on Sam during the Supernatural convention in The Real Ghostbusters. Although she breaks up with him when she begins dating Chuck, Sam pretends to be hurt by it but is actually relieved. To his surprise, Becky provides their first real lead on The Colt, leading them to meeting Crowley. They meet again in Time For A Wedding, but this time Becky drugs Sam and they get married. Becky is quick to show Sam off. Under the spell Sam is completely in love with Becky and Becky is extremly happy, but it wears off. Sam manages to get Becky to work with him to stop the Crossroad Demon Guy and she saves his life in the confrontation by killing the demon Jackson. Afterwards, Sam gets an annulment of their marriage, but feels bad for her and tells her that she will find someone who will like her for her and points her to Garth.

Dr. Cara Roberts
Cara was a one night stand in Sex and Violence with Sam. She was also the only woman to sleep with Sam and survive, until Amelia Richardson in Season Eight. The two met in the hospital where Cara works and Sam was investigating the strange cases of men killing their wives. Dean tries to make a move on her but Sam got her attention. Sam later returns for the blood samples but Cara finds that they had already been taken. With nothing else to do Sam stays and drinks with her. They eventually make love in her office. Sam leaves though without saying good bye to her.

Amelia Richardson
Sam Winchester and Amelia dated in the year that Dean went missing. They first met when Sam hit a dog and brought the dog to her clinic. Amelia didn't have a good impression of Sam and demanded he took the dog. They later meet when Sam is fixing her sink and she freaks out thinking Sam is stalking her. The two become friends, bonding over their lost loved ones and eventually start a relationship and fall in love. Amelia and Sam move in together and she even introduces him to her father who is at first cold to him, but eventually warms up. Unfortunately, Amelia learns that her husband Don is in fact alive and after learning that Don is a good man, Sam breaks it off with her to give her a chance with him. Despite this, Sam still loves her deeply and rushes back to her when Dean tricks him into thinking she's in trouble. This strains his relationship with Dean, but he is reunited with Amelia and has sex with her. Amelia loves him so much that she is willing to leave her husband for him, but Sam suggests they take time to think it through first. Amelia agrees that in a few days, whoever is willing to be in the relationship will return to the motel and if they are both there, they will be together, but she asks him not to see her again if he decides not to as it will be too hard on her. Ultimately Sam decides to stick with Dean and hunting, but unknown to him, Amelia chose him over Don and went back to the motel and was devastated to find him not there. Sam is left depressed for awhile by his decision.

Benny Lafitte
When Dean returns from Purgatory, he purposefully keeps Benny from Sam, something Sam is pissed about when he finds out. Benny and Sam first meet after Dean and Benny take down Benny's old nest and Sam comes to help. Sam immediately seems to realize Benny is a vampire and only refrains from attacking because of Dean. Possibly because of his own bad experience with supposedly redeemed monsters, Sam refuses to trust Benny and yells at Dean for always throwing in his face that he never tried to rescue him, pointing out his Benny secret. He also threatens that he may one day kill Benny and sends Martin Creaser to track him. When it appears Benny is killing again, Sam wants to hunt him down immediately, but does give Dean time to try to find out the truth. Despite this, Sam refuses to believe it and sides with Martin, even after he knocks Dean out. Sam only abandons the hunt after Dean fakes a distress text from Amelia. He later forces Dean to choose between him and Benny, saying that where they go in the future depends on that and Dean chooses Sam. Later, when Sam is trapped in Purgatory with Bobby's soul, he is shocked to see Benny who saves him and Bobby. Despite his distrust of Benny, Sam does stop Bobby from attacking immediately, calling Benny a "buddy" of Dean's though he is shocked to see him and not at all pleased. Both Benny and Sam point out the irony that Benny is rescuing Sam who wants to kill him. Despite this, possibly putting his trust in Dean knowing what he is doing, Sam at least reluctantly trusts Benny and he leads them to the portal out. Sam even offers Benny a ride out, but Benny chooses to stay behind, both because he no longer feels like he belongs on Earth and to protect Sam from a group of vampires that arrive. Understanding this, Sam gives him his Purgatory Blade and tells Dean of his fate along with the fact that he doesn't think Benny would have returned anyway. Benny's actions in Purgatory finally earn him Sam's trust and acceptance and when he learns Dean buried Benny's remains rather than burning them, he tells Dean he finally understands that Benny is different and to go ahead and leave the door open to bring him back again in the future.

Gadreel
In order to save Sam, Dean tricks Sam into saying "Yes" to the angel Gadreel, believing he is Ezekiel, so the angel can heal him from the inside of the damage from the Trials. Gadreel acts as Sam's "angelic pacemaker" through the first half of season 9, keeping him alive and slowly healing him, but keeping the truth from him by erasing his memory so that Sam can't expel him which would mean death. Gadreel occasionally uses Sam's body to do various tasks, but always returns control to him. Gadreel's presence protects Sam from Vesta and saves him when Chef Leo mortally wounds him, but after agreeing to work for Metatron, Gadreel takes full possession of him, trapping Sam in a fantasy world within his mind where he believes he is hunting with Dean. With help from Crowley, Sam learns the truth and expels Gadreel, but it severely damages his relationship with Dean. Its shown that Gadreel at least mostly healed Sam as he claimed before being expelled despite telling Sam he might be all that's keeping him alive and Castiel plans to finish what Gadreel started. Sam later tells Castiel that he could kind of sense Gadreel in his head and he felt that Gadreel felt misunderstood, not evil. After learning the truth about Metatron, Gadreel comes to the Winchesters and Castiel to offer his help. Despite what Gadreel did to him, Sam was willing to forgive him and let him help and was furious that Dean tried to kill the angel. Sam helped Castiel track down and save Gadreel and the three worked together to stop Metatron. While Sam helped Dean go after Metatron with the First Blade, Gadreel helped Sam sneak into Heaven to break the angel tablet and Metatron's power. While Dean was killed, Gadreel sacrificed himself to redeem himself for all of his actions, including what he did to Sam and save Heaven. He seemed to consider Gadreel a friend after everything he did when he switched sides as when he told Dean off for going off with Crowley rather than his "real friends" he specifically referred to Gadreel as one.

Sparrow Jennings
During Sam's soulless period, when Dean was kidnapped by fairies, Sam ignored him and had a one nightstand with a "hippie chick" from a local group of UFO followers. Angering Dean for Sam not looking for him when he disappeared.

Annie Hawkins
Annie is a hunter, in her mid-thirties. She works on her own, and has no family. She is a friend to Bobby, Dean and Sam, and in fact has slept with each of them at various times. It is unknown when these encounters occurred, although Sam tells Dean that it was during the period that he was soulless and they ended up on a case together.

Lana
A prostitute that soulless Sam slept with in The Third Man, she was very impressed with Sam's physique and prowess and even gave him her phone number so they could meet again, Sam quickly tossed the number in the garbage as soon as she left.

Other Relationships

 * Sam and Gordon
 * Sam and Ellen
 * Sam and Mary
 * Sam and Lucifer
 * Sam and John - Sam and John's relationship as we know.
 * Sam and Ruby - How they went from allies to lovers to enemies.