Supernatural - What Is and What Should Never Be Season 2 Episode 20

Dean gets a glimpse into how life would be if the demon had never killed his mother and if the Winchesters hadn't devoted their lives to killing the evil that walks the Earth. In this life, Sam is in law school and engaged to Jessica, his mother is alive, and he is leading a normal life. However, when a strange woman begins following him around and tells him that each of the people that Dean has saved has died, Dean has to decide if he wants to stay in this life or return to his life of hunting.