An episode that starts out with the boys in such a good mood…until they aren’t anymore.
So Dean is super excited and geeking out because they are hunting a werewolf, saying they are bad ass and they haven’t seen one since they were kids (something referenced again in Bad Boys). Dean just gets super excited for anything dealing with dogs…minus Hell Hounds… and canines and I actually find that so adorable.
So the boys go to meet Madison and after thinking Kurt is the werewolf they decide someone needs to watch her. Both brothers want to stay with her, which is interesting to me because usually if Sam shows interest in a girl Dean backs down. They play rock-paper-scissors, the first of a running joke about how Dean can never win and always uses scissors, and Sam stays with Madison while Dean follows around the stalker ex-boyfriend.
Madison has no problems hinting that she likes Sam. Hell, she dumps all of her underwear on the table in front of him. The two start to become close and that night she turns and goes to kill Kurt, knocking Dean out in the process. Realizing she is the werewolf, Sam is upset before he realizes Madison has no idea what is happening. Sam decides to stay with Madison and have Dean go find the wolf turning people. Dean does, and it’s Glen. Dean remarks that it’s sad because Glen had no idea what happened.
Madison, who now has proof and accepted what they boys said, finds them and invites them to stay the night with her to make sure she doesn’t turn. Sam and Madison end up together. After Jessica died, Sam has had three actual ‘love interests I guess? The first was the girl from the Hook Man, where he likes her but refuses to do anything, saying he can’t after losing Jessica. Then they meet Sarah, and Sam actually really does like her. However he’s too afraid of her getting hurt and doesn’t want to risk it. Now with Madison, he wants to give it a chance. He really does like her. He thinks she’s intelligent, independent, and amazing. he really wants to help her and is so upset at the lot she was given, turned into a monster without knowing and not having any control over it. And for Madison, here is a guy who risks a lot, put his life in danger, to save her, a woman he had no idea existed a week ago.
When they realize they have no options, Madison is the one to make the final decision. She decides since there is no known cure she doesn’t want to chance it. Later we see some werewolves who can control it like Garth, but even then it’s a special case where they naturally have the ability to do so. If the cure was known at that time too, there was no way they could use it either as it requires the blood of the sire as well as Madison to have not killed anyone yet.. Madison tells Sam she wants Sam to kill her, and this ends up mirroring Sam begging Dean to be the one to kill him.
We see Dean is also upset. He knows Sam cares about Madison, and knows from experience it’s nearly impossible for Sam to be the one to pull the trigger. He and Sam go into another room and Dean offers to do it, but Sam begs him to let him do it because Madison asks him to do it. Sam is crying as he goes into the room and kills Madison, and Dean is too for the pain his little brother is in.