Sam Winchester's 10 Love Interests In Supernatural Explained

However, interestingly, Sam actually had more onscreen love interests than Dean in Supernatural, and one of his relationships was even shown in the pilot episode. Having struggled with the grief of losing his brother more than once, as well as being soulless for a brief time, Sam had quite a few love interests throughout Supernatural to keep him company, although there were only 10 that he truly cared about.

1 Jessica Moore

First Appearance: Season 1, Episode 1

When Sam abandoned the hunter life for college, he met Jessica Moore through a mutual friend called Brady. Sam and Jess lived together and dated for a year before Dean whisked Sam away on the Woman in White hunt seen in the pilot, in the hopes that they would find their missing father. Unfortunately, when Sam returned, Jess was killed the same way as his mom; burned up on the ceiling by Azazel. In later seasons, it comes to light 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 in hunting once again, driven by the need to find the demon that had now killed two of his loved ones. Considering Sam wanted to marry her and that he still references her in later seasons, Jess really should’ve been utilized in more episodes of Supernatural as not much is really known about her personality beyond what is seen in the pilot.

2 Lori Sorensen

First Appearance: Season 1, Episode 7

Lori was a pastor’s daughter who was at the center of a string of murders involving the urban legend known as “the Hookman.” The episode highlighted Supernatural’s horror movie per episode plan as a prostitute-killing ghost with a hook hand, called Jacob Karns, hunted people down in a slasher-like fashion. After Karns’ death, the hook was melted down 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 pushing Lori into dressing 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 kiss, showing their mutual attraction. However, it was too soon after Jess’ death for Sam to pursue the relationship with Lori any further. Therefore, when Dean suggested that they stay in town for a while, Sam declined his 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 on a date with Sarah to gain information about the haunted painting but found that he was attracted to her. Surprisingly, when Sarah found out about the case, she was somewhat helpful in their investigation due to her stubborn nature, prompting Dean to comment “marry that girl.” Sam was initially reluctant as Jess’ death was still quite recent, but he kisses Sarah as they’re about to leave, so the Winchesters to stay for a while longer.

Sarah also appears in season 8 as Crowley begins to hunt down every person they have saved, starting from the beginning. In “Clip Show,” Sam and Sarah reunite in less-than-ideal circumstances, and Sam learns that she is happily married and that her daughter’s first birthday is a month away. However, in a horrible twist of events, Sarah is choked to death by Crowley’s hex bag spell which was hidden inside a phone.

4 Madison

First Appearance: Season 2, Episode 17

Referred to as “the first woman since Jessica [Sam] really loved” by Sera Siege, the publisher of Carver Edlund’s Supernatural books, Madison appeared in one of Supernatural’s most memorable episodes, “Heart.” In the episode, Sam and Dean catch wind of a werewolf case in California, with Madison at the center of it all. Originally believing Madison’s possessive ex was to blame for the killings, Sam stayed behind to guard Madison all night and the two started to bond. However, Sam and Dean quickly discover that it is Madison who is the werewolf, although she has no memory of what happened.

The Winchesters try to cure Madison, and when she did not turn that night (as she didn’t fall asleep), Sam and Dean believe it has worked. With the case resolved, Madison and Sam have sex, but Madison suddenly transforms in the night and escapes. Eventually returning to the Winchesters, Madison asks Sam to shoot her so that she won’t kill anyone else. A tearful Sam then kills her offscreen, despite Dean’s offer to do it instead, marking one of the saddest character deaths in Supernatural.

5 Ruby

First Appearance: Season 3, Episode 1

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

Following 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 both Sam and Dean into thinking she is trying to help them, however, in season 4’s finale, her true intentions are revealed. Once Sam kills Lilith, Ruby reveals that Sam has released Lucifer and broken the final seal due to her manipulations. Dean, with the help of Sam, kills her for what she did.

6 Becky Rosen

First Appearance: Season 5, Episode 1

Supernatural has a penchant for being meta, with numerous references and nods to the fandom throughout the show. Yet no one quite encapsulates just how meta Supernatural can be than Becky Rosen. Becky is a fan of the Supernatural book series written by Carver Edlund, aka Chuck Shurley (who is later revealed to be God himself). As an avid fangirl, Becky has read every book and even writes fanfiction about the Winchesters. Her infatuation eventually leads to her meeting the brothers in real life, wherein Becky shows a particular obsession with Sam.

Becky appears quite a few times throughout Supernatural and continually flirts with Sam, despite Sam not reciprocating and her relationship with Chuck at the time. However, in “Season Seven, Time for a Wedding!” Sam reciprocates Becky’s feelings, and the pair are due to be wed. Afterward, Sam’s affections are proved to be fake as he is under a love spell, and the marriage is annulled. In season 15’s “Atomic Monsters,” Chuck visits Becky to reminisce about their relationship and the Winchesters, and it was revealed that Becky had moved on and settled down with a family of her own.

7 Amy Pond

First Appearance: Season 7, Episode 3

When Sam was a teenager, he protected a girl called Amy Pond from some bullies, and the two connected due to their absent parents and life on the road. Amy was Sam Winchester’s first kiss. Unfortunately, Amy’s mother returned home and told Amy they had to leave as the hunters had found them. Sam, who had been hiding in the closet, emerged and Amy’s mother grabbed him. To save his life, Amy stabbed her mother, killing her, and implored Sam to run away with her. Sadly, Sam refused and told her to run, despite her being a monster.

In season 7, Amy starts killing people in order to feed her ill son, attracting the attention of Sam and Dean. Sam confronted Amy, who explained how the dead brains she had been eating in the morgue were not sustaining her son through 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 about Amy’s murder, he struggled to forgive Dean for a long time.

8 Amelia Richardson

First Appearance: Season 8, Episode 1

Amelia first appeared in season 8, episode 1, and consistently shows up through Sam’s flashbacks throughout the season. After Dean is transported to Purgatory, Sam accidentally hits a dog with the Impala, causing him to rush to the vet. The vet, Amelia, tends to the dog and convinces Sam to take care of him. This interaction eventually leads to a relationship shown through flashbacks; Amelia and Sam are a happy couple who bond over their missing loved ones – Amelia’s husband, Don, had died in Afghanistan and Sam’s brother went to Purgatory – with Sam having a good relationship with Amelia’s father.

Yet Supernatural has a trend of dead characters returning, and Don is revealed to be alive, causing Sam to leave Amelia so that she can be with him. However, when Dean tricks Sam into visiting Amelia again, it dredges up old feelings and Amelia proposes an ultimatum; if either one wants to continue the relationship, they should go to the motel “and we’ll know.” Sam decides to move on from Amelia to continue hunting, thinking she would move on too. Amelia turns up at the motel alone.

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 attacking her family as a child. Eileen and Sam met on a case hunting the very Banshee that killed her parents, and the pair communicated using what little sign language Sam knew from college. They developed a friendship afterward and continued to stay 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 makes a reappearance as a ghost and helps Sam to find the spell for a soul bomb. During their search, Sam also finds a spell to resurrect her, which surprisingly works. Sam and Eileen then become very domesticated in the Bunker, with Dean seemingly 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 called off in “Last Holiday,” as Sam and Eileen go on a date.

10 Velma Dinkley

First Appearance: Season 13, Episode 16

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

Realizing that the Scooby Gang cannot handle the fact that real ghosts exist, Sam and Dean pretend that the ghost was Cosgood Creeps in disguise the whole time. Satisfied with her deductions, Velma teases Sam about ghosts not being real before dipping him and kissing him. Although Sam never outwardly expressed any romantic interest in Velma, he seemed pleased by the kiss, hinting that it was not one-sided, marking one of the strangest romances in Supernatural.