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* [[Jessica Moore]] (deceased) - Sam's girlfriend while he was at [[Stanford]]. He was about to propose to her when [[Azazel]] had her killed by [[Brady]], in order to force Sam back into hunting.
* [[Lisa Braeden]] and [[Ben Braeden]] - Dean had a brief affair with Lisa when he was young, and he looked her up when he was in his last year following his deal with the [[Crossroads Demon]]. Dean returned to them following Sam's sacrifice to imprison [[Lucifer]]. He lived with them for a year. Eventually, he asked Castiel to wipe him from their memories, due to the danger and violence he felt he brought to their lives.
* [[Amelia Richardson]] - Sam had a relationship with Amelia for a the better part of a year, while Dean was and Castiel were trapped in [[Purgatory]]. They lived together in Kermit, Texas. The relationship ended when Amelia's husband [[Don Richardson]], returned after having been presumed killed in action in Afghanistan, and Sam chose to return to hunting over staying with Amelia.
* [[Benny Lafitte]] (deceased) - After their time together in [[Purgatory]], Benny and Dean have a close friendship, close enough that Benny calls Dean "brother," something he doesn't rebut and he trusts him to save Sam and Bobby. Benny never betrays Dean's trust and friendship.
* [[Charlie Bradbury]] (deceased) - An ally of the Winchester boys. Dean claims that "She's kind of like the little sister I never wanted." Even Charlie considered the Winchester boys her brothers.