Madison

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Post-coital Madison and Sam
Madison asks Sam to kill her

Madison works as a lawyer's secretary in San Francisco; her violent ex-boyfriend Kurt seems to be the prime candidate as the werewolf running around killing people after Madison's boss is killed.

A game of rock, paper, scissors results in Sam being left to guard the 'hot chick', while Dean is out investigating Kurt. There is an obvious attraction between Sam and Madison, but they spend the evening watching All My Children on TV. During the night, unnoticed by Sam, Madison leaves. She is then discovered to be a werewolf by Dean when she kills Kurt.

Sam figures out that Madison was infected when she was bitten during what she thought was a mugging a month previously. Dean kills Glen, the werewolf that made her, but it doesn't cure her lycanthropy, and after a brief interlude during which Sam and Madison have sex, she takes off when the full moon rises.

The next day, a helpless Madison asks Sam to kill her, because she doesn't want to live as a monster killing innocent people (a speech that echoes Sam's pleas to Dean in Born Under a Bad Sign). When there appears no alternative, and despite Dean's offer to do it instead, Sam shoots and (it's assumed, although the shooting takes place off-screen) kills her.

Madison is mentioned by Sam in the 4.17 It's A Terrible Life as being his fiancée, suggesting that she still weighs on his mind. He tells Dean that when he tried to call her the number redirected to (ironically) an animal hospital.

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