The challenge word is heart. I only own my own, personal ideas.

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Sam had lost a lot of women in his life.

Almost every relationship he has been in had ended in tragedy. Some hadn't.

He had seen Jess burn on his apartment ceiling. He unwillingly had to kill Madison. He willingly had Dean kill Ruby. He had annulled a loveless marriage with Becky. He had to dump Amelia for hunting. He had seen Sarah die, thanks to Crowley. Then, he had another broken heart after hearing of Eileen's death by a hellhound.

It's as though he's destined not to have a lover.

So Sam will always be heartbroken in the end.

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