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The Past Loves of Sam Winchester AKA Five relationships Sam had had and one he wished he did.

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  1. Jess

Jess was like spring, warm and welcoming the beginning of something wonderful. Sam felt alive when he was with her, shedding his old life like a baby bird breaking out of its shell. He was a new person when he was with her, someone who had never killed a vampire, or almost watched his brother die. With Jess, he was normal, a college boy whose biggest worry was failing his chemistry test. Jessica loved him unabashedly, and he loved her the same way, with the passion of a first love that he was sure would be his last.


And then she burned on the ceiling.


  1. Madison

Madison was like fall, brisk and tart and exciting. She was the first person he’d felt anything for since he lost Jess, a completely different flavor than the one he had gotten so used to. She made him want to believe that the monsters he’d grown up to fear could be people like anyone else, that they could live normal lives, even fall in love. She tasted like the first breath of autumn when he kissed her, like the smokiness of a bonfire. Madison came alive in his hands, and she made him feel more alive than he had in months. In her, he had hope that he wasn’t completely broken.


And then she asked him to kill her.


  1. Sarah

Sarah was like winter, a bright snowy sunset of a woman. She was every bit as beautiful as the art displayed displayed in her father’s gallery. And she was clever too, didn’t sit back and let Sam and Dean save her from the cursed painting that was wreaking havoc. She put herself at risk, in order to get to the bottom of what was going on. Sam couldn’t say that for everyone. He tried to stop his feelings for her from growing, knowing what would happen. People who he cared about only ended up dead, he hadn’t accounted on her returning his feelings. He let himself enjoy a couple days with her, hoping beyond all hope that someday, he could go back for her.


And then she died.


  1. Ruby

Ruby was like summer, hot, brutal and unrelenting. She was addictive in a way he hadn’t tasted before, enticing him down to the very soul. He knew he should stay away from her, he had known from the beginning what she was and what she was capable of, but he didn't care. There was something freeing about being with her, ignoring the rational part of his brain and do what felt good for once in his life. She was always up for anything, always ready to do what needed to be done, even if it wasn’t the best way. He felt like she was the only one who understood him, the only one who knew what he really was.


And then she betrayed him.


  1. Amelia

Amelia was like spring, like a second chance, like the rebirth of his perfect life. Dean was gone, and he’d told Sam not to look for him. Sam didn’t know how he could even begin to put his life back together, and then he hit a dog. Just another bad thing in a string of bad things that always happened to him, and then he met Amelia. Before he knew it, they were living together, living the kind of live he had always dreamed of. He told her about Dean and she told him about Don, and together they began gather the broken pieces of their respective lives, and used them to build a new one together. But Dean came back, and there was no room for Sam.


And then he left her.


+1. Gabriel

Gabriel was like no one Sam had ever known before. He was power and energy wrapped in an enigma, and Sam had barely even begun to scratch the surface. He hated Gabriel and he admired him. Gabriel had tortured him, played on his pain, but he had also help him see his faults, and in the end, Sam forgave him. But it was too late, by the time Sam realized the depth of his feelings for the archangel, he was lying dead on the floor of a dirty motel. He’d gone up to bat for them, thrown himself into the fire, and paid with what he’d been running from his entire existence.


Sam had lost so many people he loved, it was hard to say which one had hurt the most. But this one, this hurt in a different way, because Gabriel never knew how he felt about him, and now he never would.


Sam buried whatever had been growing between them in the graveyard of his past loves, with all the others, and kept moving forward.