|Dates||????-2007 (killed by Sam)|
|Location||San Francisco, California|
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 2.14 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.
Dean mentions Madison's fate at the beginning of the hunt, suggesting that it will be a good opportunity to take Sam's mind off her.
When in an alternate reality created by Zachariah where he and Dean are not brothers and are unaware of the supernatural, Sam's fake memories include Madison as his ex-fiancé, with Sam's attempt to call her number resulting in him being redirected to an animal hospital.
While Sam and Dean are talking with The Publisher of the Supernatural series, the publisher mentions that she found Sam's decision to shoot Madison - "the first woman since Jessica he ever loved" - to be a particularly moving part of the series.