Sam Winchester has the toughest luck when it comes to relationships. Getting close to the younger Winchester means chaos and a tragic fate. We have seen that it didn’t end well for the numerous women who got closer to him. But why does Sam Winchester have such a complicated romantic life? Many people believe that all those who have been with Sam met a tragic end, but it’s not entirely true as there are many women who survived even after being with Sam.

So Take A Look At 5 Interesting Facts About Sam Winchester And His Relationships


Supernatural started with him and Jessica. The two were living together and Sam planned on marrying Jessica. Even though despite being in love with Jessica, Sam never shared his hunting life with Jessica to keep her safe. It was also the tragic demise of Jessica that pushed Sam back into the hunter’s life. Later, we discover that it was all part of Azazel’s elaborate plan in order to get Sam back from the sidelines. In the beginning, the CW Network wanted to keep Jessica as a regular character, but Kripke had other plans. They suggested the idea of making Jessica a demon who entered Sam’s life with a purpose and would then betray him when he learns that his life is plagued with the demons. It is also possible that Sam has foreseen the demise of Jessica due to his precognition.


Eileen Leahy is a hunter who became a hunter after losing his parents to a Banshee. The Banshee attack also took away her hearing and like the Winchesters, her grandfather was a a member of Man of Letters. Sam crossed paths with Eileen while investigating the case of a Banshee. Sam using the little sign language he learned at Stanford to communicate with Eileen. Eileen is the first deaf hunter in the SPN who also remained deaf even after becoming a ghost and her hearing didn’t come back after she was resurrected.


While Sam have had numerous romantic relationships with humans, but interestingly he has been involved in romantic relationships with non-humans too. Her first non-human lover is Amy Pond who turned out to be a Kitsune. Second non-human lover of Sam is Ruby who always manipulated and used Sam for her selfish motives. When Dean was gone to the underworld, Ruby and Sam got closer, it was Ruby who got Sam addicted.

Interestingly, both of the non-human lovers of Sam met their tragic end at the hands of Dean Winchester. While Sam let Amy Pond go after learning about her son, but Dean tracked her down to a hotel and didn’t believe her. Dean even threatened Amy’s son that he’ll come after him if he also preys. After discovering the truth of Ruby, Sam held Ruby down while Dean used the demon knife on her.


There are many who survived even after ‘spending time’ with Sam Winchester.

  • In the episode ‘The Third Man’, Sam hired Lana to spend the night, Lana offered her phone number to Sam who tossed it away.
  • Dr. Cara Roberts who appeared in Season 4 working at a hospital which is being investigated by the Winchesters. After getting drunk, she flirted with Sam and the duo had a ‘wild time’.
  • In Season 11, Sam was told by Dean to enjoy and have some fun. In the episode ‘Baby’, Sam spent time with a waitress named Piper who is also alive.
  • In Season 6, Sam Winchester had some quality time with Sparrow Jennings who became interested in Dean’s disappearance and the entire UFO Story. When Dean returned, he found Sam and Sparrow together in the motel.
  • In Season 8 when Dean was lost in the Purgatory, Sam met Amelia after he had accidentally hit a dog. Both of them bonded over the trauma of loss and began a relationship. But after learning, her husband Don is alive, they both broke up when Sam chose hunting with Dean over Amelia whereas Amelia chose him over Don.


While there are numerous women who have experienced a tragic fate due to their association with Sam Winchester.

  • Annie Hawkins was a hunter who was involved with Sam when he had no soul. After she goes to a haunted house to investigate, she meets her demise and becomes a ghost. But along with the ghost Bobby and the Winchesters, they manage to solve the case.
  • In Season 1, the Winchesters dealt with the case of a hunting painting. It was then Sam crossed paths with Sarah Blake who put her life in the danger to help the Winchesters despite the risk. She expresses her love for Sam, but hunting life forces Sam to move away. In Season 8, Sarah becomes a victim of Crowley who uses her to get back at Sam from stopping him shutting the doors to the underworld.
  • In Season 2, the Winchesters came across a girl named Madison who became a werewolf after being bitten by her neighbor. When Madison would sleep, she would turn into a werewolf, unable to control her impulses and instincts. Sam and Madison became attracted to each other after Sam stayed behind to protect Madison. The Winchesters tried curing Madison, but they cannot, Madison asked Sam to end her because she cannot hurt the innocents.


By Ivaylo Angelov

Ivaylo Angelov born in Bulgaria, Varna graduated School Geo Milev is Tvserieswelove's Soaps Editor and oversees all of the section's news, features, spoilers and interviews.