Sam Winchester and his other relationships he encounters in his life. The minor friends, enemies, and lovers he has encountered are listed here.
Sam met Jessica Moore met through their mutual friend, Brady. The two quickly fell in love, to the point that they shared an apartment. Although Sam was so enamored by Jessica that he planned on marrying her, Sam kept the rule to never reveal his hunting past to her, deciding it would be safer that way.
The two had been together for over a year by the time Dean arrived to drag Sam off to hunt a woman in white. Sam intended to return and Jessica waited for him with cookies. However, when Sam returned to their apartment, he discovered Jessica on the ceiling with her stomach cut open. She soon burst into flames, and died exactly the same way his mother had 22 years earlier.
Sam was heartbroken and did not get over her death for a long while. Her death would be avenged when Sam discovered that Brady had set them up, as part of Azazel's plan to lure Sam back into hunting. In retaliation, Sam killed Brady.
Years after Brady's death, Sam still remembered Jessica. While under torture by Lady Toni Bevell, Sam saw a vision of Jessica's death and called out to her. It is unknown if Sam still regrets never warning Jessica about her death, as he had foreseen it days before it happened.
dog and brought the dog to her clinic. Amelia didn't have a good impression of Sam and demanded he take 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 has feelings for her and rushes back to her when Dean tricks him into thinking she's in trouble. This strains his relationship with Dean(but like always, is fixed after some hard choices), but he is reunited with Amelia and has sex with her. Amelia decides 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. 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 upset to find him not there.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.
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.
Annie, like a number of Sam's lovers, ended up dead. She was killed by Whitman Van Ness.
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, leaving Sam 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 meet Crowley. They meet again in Season Seven, 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 extremely happy, but it eventually 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.Sex and Violence. The two met in the hospital where Cara worked 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 returned for the blood samples but Cara found that they had already been taken. With nothing else to do Sam stayed and had drinks with her. They eventually made love in her office. Sam departed without saying goodbye to her.
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.
In Ankeny, Iowa, Sam and 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.
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 devastating 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. Sera Siege referred to her as the first woman Sam really loved since Jessica after reading the Supernatural books.
The first time Sam and Meg met, they were both trying to make their way to California. He was unaware that she was actually a demon working for Azazel and was 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 over 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 meet, Sam realizes 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 tendencies, she was very attracted to Sam and seemed to want to try and get together with him, although that was actually just an act to gain trust. When she returns, Sam captures her and 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 grateful towards 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. Later, after Dean shoots one of her Hellhounds, they kill Jo and necessitate Ellen's death as well, 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 it's 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 and his brother snare 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 in 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 it's 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.
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 realized 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 could be together, beginning his moving on from Jessica. Dean later suggested they go visit her again, but Sam refused. 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.
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.
During his time trapped in the television show "Scooby-Doo," Velma fell for Sam's "broad shoulders" and the two shared a kiss.
When Sam was 6 months old, Azazel entered his home in Lawrence and fed him demon blood. This was a ritual meant to turn Sam into a Special Child. Mary's interruption of the ritual led to her death and the destruction of Sam's home. As a result, Sam grew up without a mother and was raised to become a hunter so he could one day avenge Mary's death and kill the demon responsible.
As Sam and his family hunted down Azazel, said demon kept a close eye on Sam and every other Special Child, although he came to favor Sam above all others. He instructed various demons to possess people close to Sam, from his teachers to his friends, as a means to keep an eye on the boy.
When Sam ran away from his family to begin a new life in college, Azazel felt he could not allow Sam to waste his gifts as a soldier by living a normal life, so Azazel instructed another demon to possess Sam's friend Brady and have that demon introduce Sam to Jessica Moore. Azazel planned to have Jessica killed from the moment Sam met her, and it was Jessica's death that drove Sam to become more focused in his hunting in hopes of avenging both Mary and Jess.
Sam and Azazel met briefly in "Salvation" when Sam caught Azazel in the middle of feeding demon blood to Rosie Holt. Azazel teleported out of the nursery to avoid being shot by the Colt. Unbeknownst to Sam, Azazel went onto possess John Winchester and lured Sam and Dean into a trap by pretending to be their father. This became Azazel and Sam's very first official meeting since Sam was a baby. Although Sam threatened to kill Azazel for what he did, Azazel did not take him seriously and instead focused on Dean. As Azazel tortured Dean, John regained control of his body long enough to give Sam the chance to kill the demon, but Sam refused, since Sam did not want to sacrifice his own father for the mission. Azazel fled the scene, much to John's chagrin.
Months later, Azazel kidnapped Sam and many other Special Children in order to have them fight each other to the death, and take the winner as the leader of his demon army. Azazel was rooting for Sam to win, and personally spoke to Sam in his dreams to give him encouragement. Sam was killed in battle by Jake Talley, but was soon resurrected by Dean in a crossroads deal, something Azazel thanked Dean for. When Azazel threatened to kill Dean again, Sam tried to save his brother but was pinned to a tree, forced to watch as Azazel pointed the Colt to Dean's head.
|“||I'll get to you in a minute, champ. But I'm proud of you— knew you had it in you.||”|
— Azazel's last words to Sam
in All Hell Breaks Loose - Part 2
In the end, it was John who helped Dean execute the demon and avenge Mary and seemingly Jessica. Sam would not discover until a few years later that Azazel had ordered Brady to kill Jessica, and through Lucifer, Sam would also discover the number of people Azazel had possessed to watch over Sam. All these demons and their hosts were killed by Sam himself, thus ending Sam's connection to Azazel once and for all.
Years later, Sam learned what kind of demon Azazel was from Crowley and Castiel. He was shocked to hear how powerful the Princes of Hell of were.
When Dean returns from Purgatory, he purposefully keeps Benny from Sam, something Sam is angry 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.
Sam met Eileen when he visited Oak Park Retirement Living to investigate a case involving the death of one resident. Eileen, in her maid guise, attacks Sam and accuses him of being a Banshee. Sam allows her to test him using her golden knife and informs her that he is a hunter. Eileen is surprised, and admits she is a hunter too.
After the misunderstanding, Sam and Eileen befriend each other and agree to work together in finding the Banshee, who had been responsible for the deaths of Eileen's parents. Sam tries to communicate with Eileen, who is deaf, by using some sign language he learned at Stanford University, but he is admittedly not very good at it.
With the help of resident Mildred Baker, the two hunters successfully vanquish the Banshee. From then on, Sam and Eileen develop a friendship and keep in contact. Sam learns proper sign language specifically so he can talk to Eileen.
The two take part in another hunter together about a year later when Eileen finds a lead on Kelly Kline, the mother of Lucifer's unborn child. Using the information she gathered, Sam and Dean are able to locate Kelly and attempt to take her back to the Bunker, but Kelly's protector Dagon interferes and takes Kelly away. In an attempt to stop Dagon, Eileen fires The Colt, but the bullet hits British Man of Letters operative Renny Rawlings instead.
When Mick Davies attempts to kill Eileen in retaliation as per British Men of Letters protocol, Sam is the one to talk him out of it, insisting it was an accident. Back at the bunker, Eileen has a break down and Sam comforts her. The two hunters part ways soon after.
A few weeks later, Eileen is killed by a hellhound. Sam learns of this from Jody Mills, and he and Dean visit the morgue to identify the body. Sam is shown very unhappy with the loss, even more when a handful of other hunters have been killed in a short period of time. He receives a letter sent by Eileen a while ago that informs him of the possibility of wiretapping, and in fear of her life, Eileen wished to stay at the Bunker with them.
The letter helps Sam and Dean find out about the wiretaps inside their bunker. They use it to try and trick the British Men of Letters into a trap, and manage to capture Lady Toni Bevell, who confirms Sam's suspicion that Eileen was killed by the Brits.
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. It's 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 when Dean tried to kill the angel. Sam helps Castiel track down and save Gadreel and the three work together to stop Metatron. While Sam helps Dean go after Metatron with the First Blade, Gadreel helps Castiel sneak into Heaven to break the Angel Tablet and Metatron's power. While Dean gets killed, Gadreel sacrificed himself to redeem himself for all of his actions, including what he did to Sam and save Heaven. Sam seems to consider Gadreel a friend after everything he did when he switched sides as when he told Dean off for going with Crowley rather than his "real friends", he specifically referred to Gadreel as one.
Unlike his brother, Sam has always been a strong believer in God, and prayed to him throughout his life. Unknowingly, Sam would meet God during the events of The Monster at the End of This Book, but would know him simply as "Chuck Shurley". It should be noted that God, as Chuck, expressed disappointment in Sam's addiction to demon blood. He chose not to add this piece of information to the Supernatural books to keep Sam from appearing "unsympathetic".
Sam was initially disbelieving of Chuck's prediction that he would sleep with Lilith. When Lilith did arrive, Sam intended to kill her, but almost got killed himself until Chuck arrived at his location. This sent Lilith running in fear of the archangel that was guarding Chuck.
Sam met Chuck again in The Real Ghostbusters, during which Sam threatened to harm Chuck if he continued publishing the Supernatural books. Sam was, however, glad to know that Becky liked Chuck.
Afterwards, Sam rarely spoke, or even mentioned Chuck, and since Sam was a practical person, he did not rely much on praying though he still prayed, even after he felt God had abandoned him and Dean during the Apocalypse. Sam's last known prayer was in Form and Void, which went unheard by God but was picked up by Lucifer instead.
In We Happy Few, Chuck admitted to being God to Sam and Dean by teleporting them to the bunker and even used the soul of Kevin Tran to fully convince the brothers. While Dean was displeased and resentful, Sam was notably enthusiastic with finally meeting God though nervous because of their last encounters, and began bombarding him with numerous questions until Dean told him to stop.
Sam did grow a little uncomfortable with God's apparent lack of concern for Lucifer, who was being held captive by Amara. After rescuing Lucifer, Sam helped to bring father and son together through a therapy session. He then helped God devise a plan to attack Amara, and personally recruited the witches for this cause. God also put a protection around Sam, as noted by Clea.
Privately, Sam and God discussed passing the Mark onto Sam, since Sam was the only candidate not yet tainted by the Mark. However, the attack on Amara failed, and God was left dying on the floor. Sam helped to carry him outside. Afterwards, Sam remained by God's side, occasionally checking on him, until God himself disappeared.
Henry is Sam's paternal grandfather. Sam first met him in As Time Goes By, when the latter time traveled to get away from a demon named Abaddon. After learning who he is, Sam was shocked to meet him as the latter was to meet him and Dean. Unlike his brother who is resentful to him, Sam is accepting of him and correctly believed that it wasn't his fault for not being there to raise John. Sam was confused that Henry is disappointed in him and Sam not being in Men of Letters before criticizing him for abandoning his family.
After Henry reads John Winchester's Journal, he tries to undo his mistake and traveled back to his son. Aware that this would alter history, Sam was worried about him and Dean went stop him.
After Abaddon abducted Sam in exchange for Henry, Henry and Dean went to save him. This caused Henry to make a plan, the two defeat Abaddon at the cost of Henry. Sam was horrified at his grandfather's fate, as the latter uses his final moment to express pride in them and their father.
The brothers then bury their grandfather in the cemetery of his fellow deceased Men of Letters, and realize the significance of all Heaven positioning the brainy Winchesters and brawny Campbells together to produce them. Sam even wondered what their father would of been like if he still had his father.
In 2006, Sam meets a 16 years old named Matt while investigating a case with Dean involving insects. The brothers initially suspect Matt is the culprit due to his fascination in insects, but they soon realize he is not the cause.
Sam manages to bond with Matt over their shared disagreements with their respective fathers. Matt and his father do not get along and rarely see eye to eye, to the point where Matt refers to his father by his first name. Sam recalls that John was also hard on him in a similar manner, though Dean disagrees.
At one point, Sam excitedly tells Matt to expect college in two years time, describing it as something wonderful. Later on, Matt helps Sam and Dean rescue his family from the curse which is causing the insect problem. Once the case is solved, Matt and his father reconcile, much to Sam's delight.
Sam met Mick Davies while under interrogation and torture by Mick's co-worker Toni. Unlike Toni, Mick presented himself as a friend and even took Toni away back to England. Sam responded to Mick's kinder gesture by trusting him enough to call him for help in dealing with Lucifer. Although Sam hung up too soon, Mick alerted Arthur Ketch as the call made him worry if Sam was in trouble.
Sam met Mick again while escaping Site 94. Mary and Castiel had asked help from Mick and Arthur in locating Sam and Dean. They did not interact and Sam and Dean only showed distrust in Arthur. later on, Mary brought Sam to the British Men of Letters compound so he could partake in Mick's assigned protect to wipe out America's vampires. When the Alpha Vampire retaliated, Sam taught Mick how to make the bullets for The Colt so they could kill the Alpha. Their combined efforts led to the Alpha's death and Mick's survival, as well as Sam joining their ranks.
Now one of their own, Mick decided to send Sam a list of potential hunts. When Sam revealed this fact to Dean, Dean agreed to join the Brits out of trust for Mick. In order to gain field experience, Mick joined the brothers on a werewolf hunt, however, Mick's loyalty to the British Men of Letters code drove him to kill a teenager who was turning. This upset Sam so much he refused to speak to Mick or listen to any excuses, though Mick proved useful when he had a means to locate Claire Novak and cure her of her transformation.
Their relationship clearly improving, Mick was able to pay Sam and Dean a visit at the Men of Letters bunker and share a drink with them while they discussed Lucifer's son. Mick slept there for the night and joined them on a hunt for Kelly Kline, the child's mother. While Mick and his associate Renny Rawlings wanted the child aborted, Sam argued, preferring to deal with the baby differently. They were soon interrupted by Dagon, who came to take Kelly away. Eileen accidentally killed Renny in an attempt to kill Dagon, and Mick - ever loyal to the code - tried to kill Eileen.
It was Sam who talked Mick out of it, convincing Mick to follow his own code. Sam's speech to Mick was reminiscence of his speech to Max Miller and Magda Peterson, in which he urged both not to kill someone. Although Mick was talked out of killing Eileen, his newfound dislike in the code led to his own death. The same happened to Max and Magda.
Sam does not find out about Mick's death until weeks later, when a captured Lady Toni Bevell casually tells him and Dean the truth. She even admits he was killed because he held sympathies for the Winchesters. Sam is visibly unhappy about Mick's death, having thought him alive and in London as told by Arthur Ketch.
The witch Rowena is a reluctant ally of Sam to whom he asks for help whenever situations become too difficult or involve witchcraft. Sam's first assignment for Rowena was to help find a way to remove the Mark of Cain from Dean's arm, while forcing her to serve as Charlie's subordinate. Sam even invented the witch-killing bullets to ensure he could make Rowena do what he wanted. He was also willing to kill Crowley, another useful and reluctant ally, if it meant Rowena would help him.
Rowena completes the task and frees Dean of the Mark, but she also places the Attack Dog Curse on Castiel, causing him to go on violent rampages. Sam hunts down Rowena and threatens her with witch-killing bullets until she frees Castiel of the curse. The third time Sam needs Rowena's help is when Sam needs to speak to Lucifer but also needs a safe way to do it, and Rowena is the only one who can read the Book of the Damned, which tells a way of safely contacting Lucifer without freeing him from his Cage.
This time, Rowena betrays Sam by secretly working for Lucifer, enabling Lucifer to physically hurt Sam in an effort to get Sam to say "yes". Rowena's alliance with Lucifer ultimately leads to Castiel being possessed by the archangel. When Sam and Dean find out about this, Sam requires Rowena's help again to try to free Castiel of possession, to no avail.
Sam and Rowena become allies yet again under God's command. Their combined efforts were supposed to help lock The Darkness away, but the plan was unsuccessful. It was Sam who had been sent to recruit Rowena and the witches to join the team, and while Rowena could help very little in the initial plan, it was Rowena who helped to create the soul bomb intended to be used against The Darkness, though God and The Darkness reconciled and the bomb was no longer needed.
Sam's next encounter with Rowena is when the brothers need her help in banishing Lucifer back to his Cage. Rowena's full desire to do this enables the plan to become successful. Weeks after, Sam enlists Rowena's help again after Dean begins suffering from a memory loss curse. The two track down the Loughlin Family, but are easily overwhelmed. It is Dean who kills the witches, and afterwards, Rowena uses the Loughlin Family's spellbook to free Dean of the curse. Rowena intended to take the book back with her, but Sam stopped her before she could get away with it. This time, however, Sam admits that he owes Rowena for her help.
Sam contacts Rowena again when he and Sam learn they must find Rowena's grandson Gavin MacLeod in dealing with a vengeful spirit. Rowena did not want to partake in such, until Sam promised compensation for her help and then told her about Gavin. With Gavin's help, Sam and Dean were able to identify the ghost and find a solution on how to stop it - by sending Gavin back in time. Rowena shared their view that Gavin should return, and even helped the brothers keep Gavin away from his father Crowley, who did not want to lose Gavin.
By the time Sam needs her assistance again, Rowena is revealed to have been brutally murdered by Lucifer. Sam is visibly furious about this, especially since he had intended to use Rowena to lock up Lucifer for good, this being the very reason Lucifer had killed Rowena in the first place. Fortunately, Rowena is still able to resurrect herself and helps the brothers with another witch case. Sam and Rowena briefly bond over their shared trauma of seeing Lucifer's true face. Sam admits to Dean that if Rowena plans to backstab them again he will hunt her down and shoot her himself but he also hopes that if Rowena ever re-encounters Lucifer, she will make the archangel suffer.
During Funeralia, after Rowena goes about killing people, Sam feels guilty since he let her obtain her full power. It is revealed by Jessica, that Sam is always the one to permanently kill Rowena and he is shocked to learn this. When Rowena calls them and tells them she wants her son back, Sam asks her to stop while Dean threatens her with the revelation of Sam being the one to permanently kill her which leaves her mildly surprised and interested.
In Exodus, Rowena keeps the rift opened long enough for the Winchesters and company to return to the main universe. While everyone is celebrating, Sam and Rowena talk and he congratulates Rowena for holding the rift open long enough to get everyone back. Sam admits that they owe her one and Rowena tells him that she plans to collect on it eventually, but smiles at Sam as she says it.
Samuel was Sam's maternal grandfather, who Sam was named after. During Season 4, Sam learns about him from Dean and was amazed to hear they come from a long line of hunters. 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 for a whole year, and then Dean is brought into the picture. Samuel admits he knew something was off with Sam, who was at the time, soulless. Sam though does trust Samuel, until he chooses Dean over Samuel after Samuel is revealed to be working with Crowley. Samuel later betrays his grandsons by giving them over to Crowley, who had promised to bring Mary back.
When Sam gets his soul back, all the memories of him and Samuel are locked away. They meet again, Sam prevents Dean from killing him though doesn't trust Samuel, as Samuel noticed Sam was different as the latter told him of how he got his soul back, no thanks to him. Samuel was surprised to see the real personality of Sam and that he doesn't remember them hunting together. Eventually, Sam and Dean confront their grandfather on his actions and he is somewhat conflicted but doesn't apologize. Despite Dean threatening him, Sam is ultimately the one who shoots Samuel after he is possessed by a Khan Worm.
Sam seemed somewhat remorseful for killing him since he was still his grandfather even after Dean told him what it means to be family. After Sam accessed all his memories of his time soulless, he presumably remembered his year hunting with Samuel.
- Sam and John
- Sam and Mary
- Sam and Dean
- Sam and Bobby
- Sam and Castiel
- Sam and Crowley
- Sam and Ellen
- Sam and Jo
- Sam and Gordon
- Sam and Lucifer
- Sam and Ruby
- Sam was notorious for having lovers who died after sleeping with him. This pattern changed after Season 5, since many of Sam's lovers lived in the end, especially from his time while soulless.
- With the exception of Amelia Richardson, any lover Sam had who was more than a one-night stand are all dead.
- Although known for his kind nature, three people Sam has tried to help or comfort are now dead: Max Miller, Magda Peterson and Eileen Leahy.