Sam Winchester’s 10 Supernatural Love Interests Explained

Despite being a show about monster hunting, Sam and Dean Winchester have had many romantic relationships in Supernatural over the years. Traveling across the United States and defeating numerous supernatural beings often meant the Winchester brothers encountered some interesting characters on their travelsand some caught more attention than others. With a known reputation for being a “ladies man”, Dean Winchester’s various affairs were a persistent Supernatural trope that happened in almost every episode, and Sam was often left aside.

However, interestingly enough, Sam actually had more on-screen love interests than Dean in Supernaturaland one of their relationships was even shown in the pilot episode. Having struggled with the pain of losing his brother more than once, as well as being briefly soulless, Sam has had some love interests all along Supernatural to keep you companyeven though there were only 10 he actually cared about.

1

Jessica Moore

First appearance: Season 1, Episode 1

When Sam abandoned the hunting life and went to college, he met Jessica Moore through a mutual friend named Brady. Sam and Jess lived together and dated for a year before Dean took Sam away on the hunt for the Woman in White. seen in the pilot, hoping to find his missing father. Unfortunately, when Sam returned, Jess was killed in the same way as her mother; burned to the ceiling by Azazel. In later seasons, it turns out that Brady was working for Azazel and purposely set Sam up with Jess.

Jess’ death really affected Sam, despite her short appearance on the show. Sam had nightmares as a result of his girlfriend’s death and rejoined Dean on the hunt, driven by the need to find the demon that had killed two of his loved ones. Considering that Sam wanted to marry her and that he still references her in later seasons, Jess really should have been used in more episodes of Supernatural as not much is known about his personality beyond what is seen in the pilot.

2

Lori Sorensen

First appearance: Season 1, Episode 7

Lori was the daughter of a pastor who was at the center of a series of murders involving the urban legend known as “the Hookman.” The highlighted episode Supernatural episode-by-episode horror film planned as a hook-handed, prostitute-killing ghost named Jacob Karns hunting people in slasher fashion. After Karns’ death, the hook was melted and Hookman latched onto Lori and her father due to their high moral values. Hookman killed Lori’s boyfriend for being forceful, her roommate for forcing Lori to dress promiscuously, and attacked her father for having an affair with a married woman.

Sam and Lori bonded over the loss of their partners during the episode and even shared a kissshowing their mutual attraction. However, it was too soon after Jess’ death for Sam to continue the relationship with Lori. So when Dean suggested they stay in town for a while, Sam turned down the offer.

3

Sarah Blake

First appearance: Season 1, Episode 19

While working on a case involving a haunted painting, Sam and Dean encounter Sarah Blake, the daughter of an art gallery owner. Sam went out with Sarah to get information about the haunted painting, but found he was attracted to it.. Surprisingly, when Sarah discovered the affair, she was somewhat helpful in the investigation due to her stubborn nature, which led Dean to comment “marry that girl.” Sam is initially reluctant because Jess’s death is still fairly recent, but he kisses Sarah as they are about to leave so the Winchesters will stay a little longer.

Sarah also appears in season 8 when Crowley starts hunting down all the people they saved, starting from the beginning. In “Clip Show,” Sam and Sarah reunite under less than ideal circumstances, and Sam discovers that he is happily married and that his daughter’s first birthday is a month away. However, in a horrible turn of events, Sarah is suffocated to death by Crowley’s hexagonal bag spell that was hidden inside a phone.

4

Madison

First appearance: Season 2, Episode 17

Referred to as “the first woman since Jessica [Sam] I really loved it” by Sera Siege, editor of Carver Edlund’s Supernatural books, Madison appeared in one of the Supernatural most memorable episodes, “Heart.” In the episode, Sam and Dean learn of a werewolf case in California, with Madison at the center of it all. Originally believing that Madison’s possessive ex was to blame for the murders, Sam stayed behind to protect Madison all night and the two began to bond. However, Sam and Dean quickly discover that Madison is the werewolfalthough she doesn’t remember what happened.

The Winchesters try to cure Madison, and when she doesn’t turn over that night (since she doesn’t fall asleep), Sam and Dean believe it worked. With the case solved, Madison and Sam have sex, but Madison suddenly transforms during the night and runs away. Eventually returning to the Winchesters Madison asks Sam to shoot her so she doesn’t kill anyone else. A tearful Sam then kills her off-screen despite Dean’s offer to do so, marking one of the saddest character deaths in Supernatural.

5

Ruby

First appearance: Season 3, Episode 1

Ruby was possibly the most complicated relationship Sam had, and also one of the Winchesters’ worst mistakes. Supernatural. As a demon, Ruby first appeared in Season 3, played by Katie Cassidy, and formed an alliance with Sam to help her brother get out of his demon deal. Ruby informs Sam and Dean about Lilith and the three become reluctant allies. against the powerful demon.

After Dean’s death in Season 3’s “No Rest For The Wicked,” Ruby saves Sam’s life. Now possessing a new body played by Genevieve Cortese Ruby begins a sexual relationship with Sam and secretly gets him addicted to demon blood.the source of his powers. Ruby manipulates Sam and Dean into thinking she is trying to help them, however, in the season 4 finale, her true intentions are revealed. Once Sam kills Lilith, Ruby reveals that Sam freed Lucifer and broke the final seal due to her manipulations. Dean, with Sam’s help, kills her for what she did.

6

Becky Rosen

First appearance: Season 5, Episode 1

Supernatural has a tendency to be meta, with numerous references and nods to fandom throughout the show. Yet no one encapsulates exactly how meta Supernatural Could be than Becky Rosen. Becky is a fan of Supernatural series of books written by Carver Edlund, aka Chuck Shurley (who was later revealed to be God himself). As an avid fangirl, Becky has read all the books and even written fanfiction about the Winchesters. Her passion eventually leads her to meet the brothers in real life, where Becky shows a particular obsession with Sam.

Becky appears a few times throughout Supernatural and continually flirts with Samdespite Sam not reciprocating and her relationship with Chuck at the time. However, in “Season Seven, Wedding Time!” Sam reciprocates Becky’s feelings and the two are about to get married. Afterwards, Sam’s affection is proven to be false as he is under a love spell, and the marriage is annulled. In season 15’s “Atomic Monsters,” Chuck visits Becky to reminisce about his relationship with the Winchesters, and it is revealed that Becky has moved on and settled down with her own family.

7

Amy Lagoon

First appearance: Season 7, Episode 3

When Sam was a teenager, he protected a girl named Amy Pond from some bullies, and the two bonded over their parents’ absence and life on the road. Amy was Sam Winchester’s first kiss. Unfortunately, Amy’s mother came home and told Amy that they had to leave because the hunters found them. Sam, who was hiding in the closet, appeared and Amy’s mother grabbed him. To save her life, Amy stabbed her mother, killing her, and begged Sam to run away with her. Unfortunately, Sam refused and told her to run away, despite her being a monster.

In season 7, Amy starts killing people to feed her sick sonattracting the attention of Sam and Dean. Sam confronted Amy, who explained how the dead brains she ate at the morgue were not sustaining her son during his illness, leaving her no choice but to kill, so Sam decided to let her go. Dean, on the other hand, was less forgiving and secretly killed Amy behind Sam’s back. When Sam learned of Amy’s murder, he struggled for a long time to forgive Dean.

8

Amelia Richardson

First appearance: Season 8, Episode 1

Amelia first appeared in Season 8, Episode 1, and appears consistently in Sam’s flashbacks throughout the season. After Dean is transported to Purgatory, Sam accidentally hits a dog with the Impala, sending him running to the vet. Veterinarian Amelia takes care of the dog and convinces Sam to take care of him. This interaction eventually leads to a relationship demonstrated through flashbacks; Amelia and Sam are a happy couple who bond over their missing loved ones – Amelia’s husband Don died in Afghanistan and Sam’s brother went to Purgatory – with Sam having a good relationship with Amelia’s father.

Yet Supernatural has a tendency for dead characters to return, and It is revealed that Don is alive, causing Sam to leave Amelia so she can be with him.. However, when Dean tricks Sam into visiting Amelia again, it brings up old feelings and Amelia proposes an ultimatum; If either of you wants to continue the relationship, you should go to the motel.”and we will know.”Sam decides to leave Amelia to continue hunting, thinking that she would also move on. Amélia appears alone at the motel.

9

Eileen Leahy

First appearance: Season 11, Episode 11

Eileen Leahy was a hunter who lost her parents and her hearing due to a Banshee that attacked her family as a child. Eileen and Sam met on a case of hunting the same Banshee that killed their parentsand the pair communicated using what little sign language Sam knew from college. Afterwards, they developed a friendship and continued to keep in touch, with Sam learning more sign language to communicate better. When Eileen accidentally shot a British member of the Men of Letters, she was killed by Arthur Ketch’s Hellhound, leaving Sam distraught.

In season 15, Eileen reappears as a ghost and helps Sam find the spell for a soul bomb. During the search, Sam also finds a spell to resurrect her, which surprisingly works. Sam and Eileen then become very tame in the Bunker, with Dean apparently approving of the relationship.. When Eileen was used by God to torture Sam, however, Sam kissed her goodbye and they took a break. This was later canceled in “Last Holiday” when Sam and Eileen go on a date.

10

Velma Dinkley

First appearance: season 13, episode 16

The most surprising love interest Sam has had in Supernatural It was Velma Dinkley. In season 13, Supernatural aired one of the show’s best episodes; one Scooby-Doo crossover episode featuring an animated Sam and Dean. The episode is totally bizarre as the Winchesters try to convince the Scooby Gang that ghosts are real, leading to the characters’ breakdown. However, during the episode, Velma continues talking about “broad shoulders”, and apparently hinting at a passion for the Winchester.

Realizing that the Scooby Gang can’t handle the fact that there are real ghosts, Sam and Dean pretend that the ghost was Cosgood Creeps in disguise the whole time. Satisfied with your deductions, Velma teases Sam about ghosts not being real before diving in and kissing him. Although Sam never expressed any romantic interest in Velma, he seemed pleased with the kiss, hinting that it was not one-sided, marking one of the strangest romances of all time. Supernatural.