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During the episode ''[[The Kids Are Alright]], w''hen she met up with Sam again, she claimed that she was a [[hunter]], revealed that she knows about [[Azazel]]'s "[[special children]]", and encouraged Sam so he'd learn that [[Mary Winchester|his mother]]'s friends and relatives were all killed by Azazel. Sam later confronted her about how she knew so much and she was forced to reveal to him her identity as a demon. He immediately prepared to fight with her but she managed to talk him down by promising to help him break [[Dean Winchester|Dean]]'s deal.[[File:Sincity08.jpg|225px|thumb|left|Ruby refuses to back down as Sam considers killing her.]]
 
During the episode ''[[The Kids Are Alright]], w''hen she met up with Sam again, she claimed that she was a [[hunter]], revealed that she knows about [[Azazel]]'s "[[special children]]", and encouraged Sam so he'd learn that [[Mary Winchester|his mother]]'s friends and relatives were all killed by Azazel. Sam later confronted her about how she knew so much and she was forced to reveal to him her identity as a demon. He immediately prepared to fight with her but she managed to talk him down by promising to help him break [[Dean Winchester|Dean]]'s deal.[[File:Sincity08.jpg|225px|thumb|left|Ruby refuses to back down as Sam considers killing her.]]
In ''[[Sin City]]'', When [[Bobby Singer]] was trying to restore [[the Colt]]'s power after Dean used its last bullet on Azazel, Ruby arrived and baited him into shooting her with the defective gun; she was irritated when the gunshot "smarted a little" and ruined her shirt. She helped him [[Colt Bullet Creation Ritual|fix the Colt]] and he later brought it to Sam, who killed two demons with it to protect Dean. While Ruby was pleased by this display of Sam's new ruthlessness in his mission to save his brother, she became irritated when he questioned her motives in helping them, and threatened to take the Colt from him and help someone else. Sam pointed the gun at her but did not shoot when she reminded him that she could help him save Dean. She told him that they were in a war and that it wouldn't be easy - there would be "collateral damage" and he would have to resist his gentle nature - but that she'd be there for him.[[File:SPN 0461.jpg|thumb|225px|Ruby appears to the Winchesters.]]In ''[[Malleus Maleficarum]] ''Ruby tried to warn the Winchesters off when they investigated a [[witch]] coven that was being empowered and controlled by [[Astaroth]]. Ruby feared that Sam would be killed, but he and Dean ignored her warnings. Dean sensed that Ruby was evil and tried to kill her with the Colt, but Sam interfered and she fled. She later saved Dean when she force-fed him a potion that broke the spell Astaroth had cast to kill him. She tried to earn Astaroth's trust by claiming that she'd led Sam and Dean to her and that she wanted to serve her again, but Astaroth realized her treachery when Ruby tried to kill her: she beat Ruby down while revealing her origins as a human to the shocked brothers, then tried to exorcise her. However, [[Elizabeth Higgins]] distracted Astaroth, who was then killed by Dean.
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In [[Sin City|''Sin City'']], When [[Bobby Singer]] was trying to restore [[the Colt]]'s power after Dean used its last bullet on Azazel, Ruby arrived and baited him into shooting her with the defective gun; she was irritated when the gunshot "smarted a little" and ruined her shirt. She helped him [[Colt Bullet Creation Ritual|fix the Colt]] and he later brought it to Sam, who killed two demons with it to protect Dean. While Ruby was pleased by this display of Sam's new ruthlessness in his mission to save his brother, she became irritated when he questioned her motives in helping them, and threatened to take the Colt from him and help someone else. Sam pointed the gun at her but did not shoot when she reminded him that she could help him save Dean. She told him that they were in a war and that it wouldn't be easy - there would be "collateral damage" and he would have to resist his gentle nature - but that she'd be there for him.[[File:SPN 0461.jpg|thumb|225px|Ruby appears to the Winchesters.]]In ''[[Malleus Maleficarum]] ''Ruby tried to warn the Winchesters off when they investigated a [[witch]] coven that was being empowered and controlled by [[Astaroth]]. Ruby feared that Sam would be killed, but he and Dean ignored her warnings. Dean sensed that Ruby was evil and tried to kill her with the Colt, but Sam interfered and she fled. She later saved Dean when she force-fed him a potion that broke the spell Astaroth had cast to kill him. She tried to earn Astaroth's trust by claiming that she'd led Sam and Dean to her and that she wanted to serve her again, but Astaroth realized her treachery when Ruby tried to kill her: she beat Ruby down while revealing her origins as a human to the shocked brothers, then tried to exorcise her. However, [[Elizabeth Higgins]] distracted Astaroth, who was then killed by Dean.
   
 
Later on, Ruby and Dean had a heart-to-heart in which she confirmed that he too would eventually become a demon (which became one of his deepest fears). She admitted to him that she had lied to Sam so that he'd listen to her; she could not save Dean from Hell, but she wanted his help in preparing Sam for fighting Lilith once Dean died. She claimed that the reason why she was helping them was because, unlike other demons, she remembered how it felt to be human.[[File:Jus-in-bello-supernatural-1896671-1280-720.jpg|225px|thumb|An incensed Ruby teaches the boys "the rules of war".]]
 
Later on, Ruby and Dean had a heart-to-heart in which she confirmed that he too would eventually become a demon (which became one of his deepest fears). She admitted to him that she had lied to Sam so that he'd listen to her; she could not save Dean from Hell, but she wanted his help in preparing Sam for fighting Lilith once Dean died. She claimed that the reason why she was helping them was because, unlike other demons, she remembered how it felt to be human.[[File:Jus-in-bello-supernatural-1896671-1280-720.jpg|225px|thumb|An incensed Ruby teaches the boys "the rules of war".]]
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