Top 10 Romances on Supernatural
#10: Dean & Anna
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After being rescued by Sam and Dean, the mysterious Anna remembers her true identity as a fallen angel. Longing to feel emotions, she’d given up her angelic grace to be reborn as a human. Dean himself is trying to figure out why he was resurrected from Hell by the angels, and forms a connection with Anna over their helpless situation. Acknowledging that the angels will kill her, but wanting to feel human a last time, Anna reaches out to Dean. The two share a passionate night where it’s clear they want to be together on an emotional level as well. Unfortunately, Anna’s eventual goal of killing Sam made Dean her enemy, and her death at Michael’s hands ended any chance of reconciliation.
#9: Sam & Amelia
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Sam is left alone when Dean is sent to Purgatory after killing Dick Roman. With no clue how to find his brother, Sam decides to retire from the hunting life. A chance meeting with the widowed Amelia not only gives him a chance at happiness, but also allows him to cut himself off from the supernatural world as she never learns about his past. Being with Amelia even lets him move on from Dean, as Sam settles down to the closest thing to a normal life he’s had in a long time - if ever. While the revelation of her husband’s survival forces him to leave, Amelia promises to choose the younger Winchester brother if Sam is willing to take her. Sadly, Sam goes back to Dean when he returns to Earth while Amelia becomes “the one who got away.”
#8: Sam & Sarah
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The pursuit of the yellow-eyed demon Azazel makes Sam focus solely on revenge. So romance isn’t in his plans when he meets Sarah, but an instant connection forms between the two. Despite his reluctance to be involved with another girl soon after his girlfriend Jessica’s demise, Sam can’t ignore the obvious chemistry he has with the daughter of an art gallery owner. Her fierce nature impresses him the most, as Sarah’s able to accept the supernatural and assist the boys in their hunt. Because of their strong mutual attraction, Sam and Sarah acknowledge their feelings before he leaves. The impact they have on one another remains for years,with Sam and Sarah reconnecting later on when Crowley tries to take her life. Tragically, Sarah falls victim to the demon, leaving Sam mourning over what could have been.
#7: Dean & Lisa
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Dean generally accepts the hunter life, but Lisa stands as proof that he also dreams of settling down. Though she’s a former flame, he never forgets Lisa and even becomes a father figure to her son years after they hooked up. She remains on his mind throughout the threat of the apocalypse, and moves in with her after Sam is lost in Lucifer’s cage. Even after returning to his life as a hunter, Dean’s feelings for Lisa remain the same, and she also finds it difficult to get over him. Ultimately, his desire to keep Lisa safe is why Dean asks Castiel to remove her memories of their time together. While he does eventually move on, it can’t be denied that Lisa is seemingly the only person who could make Dean as happy as he could be when Sam wasn’t around.
#6: Sam & Ruby
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Arriving in his life when he’s searching for a way to save Dean’s soul from Hell, Ruby proves her worth by helping Sam time and again. Their relationship is taken to the next level when a vulnerable Sam grieves Dean’s death, as Ruby - in her new body - is there to “comfort” him. Sam grows to see her as someone he can share his feelings with, also drinking her blood to empower himself to face Lilith. They work so well together that it even appears as if Ruby’s feelings are genuine. However, she turns out to be working for Lucifer the whole time, breaking poor Sammy’s heart. All in all, Sam and Ruby are a perfect example of what happens when the good boy falls for the bad girl.
#5: Sam & Madison
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Initially believing her to be the target of a werewolf, Sam resolves to protect Madison. Like something out of a romantic comedy, they try to deny their obvious sexual tension in awkward ways - much to Dean’s amusement. The two are eventually able to act upon their feelings when it seems Madison is safe, leading to things getting pretty wild. It’s too good to be true, however, as her werewolf condition doesn’t end up being cured by the death of the creature who initially bit her. As a result, Madison asks Sam to put her down. A tearful Sam honors his lover’s last request, but becomes distraught at losing another woman he had opened himself up to. Madison could have been another shot for Sam at a happy romance, but fate cruelly cuts it short.
#4: Sam & Eileen
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From the moment they meet, Sam is taken by Eileen’s fierce nature. Empathetic over how Eileen lost her parents, Sam forms an effective partnership with her. They remain friendly with one another for a while, although Sam might be a little smitten - even learning sign language to communicate better with her. Her death seems to end any chance of a potential romance, that is until Sam finds a way to bring her back to life. Touched by his gesture, Eileen embraces her feelings for him, and the two slowly begin a romance. They both serve as each other’s confidante and friend, and it’s something that even Dean approves of. While Chuck’s repeated interferences threatened their relationship, Sam finally finds the courage to look past his fears and acknowledges his feelings for Eileen - though that doesn’t stop her from leaving.
#3: Castiel & Meg
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Introduced as one of the Winchesters’ sworn enemies, the demon Meg mellows down once she takes notice of Castiel. Despite not understanding how human attraction works, Castiel shockingly has a lot of affection to give to Meg, and she very much appreciates it. Then, when he’s rendered comatose after taking on Sam’s memories of Hell, Meg is the one who watches over him in the psych ward. Heavily influenced by the care and dedication he shows her after he wakes up, Meg finally turns over a new leaf and becomes one of the good guys. It’s because of her very feelings for her “Clarence” that she has the courage to face Crowley, which is a fight that leads to her demise. It ultimately took the touch of this particular angel to redeem this once-evil demon.
#2: Sam & Jessica
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You never forget your first love, and for Sam this certainly holds true. Growing up without a home, he finds the person he can have the life he’s wanted in Jessica. Charmed by her sweet nature, Sam chooses her over his family business because she made him feel loved. Although Jess isn’t seen much, an alternative reality later implies that she was supposed to be the one for Sam. Her willingness to be his safe place proves to be the foundation of their relationship. The impact she has on the younger Winchester sibling is felt even after her death, with Sam spending all of the first season in grief. The fact that she’s still in his thoughts fifteen years later signifies just how perfect their romance had been. Before we unveil our top pick, here are a few honorable mentions - which, as previously “mentioned,” consist more of the crushes, one-sided feelings, and/or short-lived love interests: Dean & Jo Because There Was Always Something Special Here Cesar & Jesse Because When You Know, You Know Dean & Amara Because Who Doesn’t Like a Dark Romance? Dean & Cassie, “Route 666” Because She Was Dean’s First Love Sam & Velma, “ScoobyNatural” Add Some Laughter to Your Romance, Sammy Fake Out #1: Sam & Dean Okay, we're talking about their literal bromance here, guys, since they're brothers and all, thief familial love - not *cough* Wincest *cough*...JUST KIDDING!"
#1: John & Mary
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The events of Supernatural are only possible because John and Mary fell in love. While their match was literally made in Heaven, there’s no doubt these two are each other’s soulmates. They represent each other’s escape from their unfulfilling lives with Mary giving up being a hunter for him, and John finally getting the family he wanted through their marriage. Their union is constantly threatened by Azazel, yet John and Mary still manage to make it through. Neither are able to move on without the other, with memories of their romance the only thing that keeps them going in life. Their eventual reunion, both in life and death, is ultimately worth all the pain. And no matter how many times they’re separated, John and Mary find a way back to each other.
