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Bobby's guilt over Karen's death causes her to inhabit his dreams.<ref name="three10">[[3.10 Dream a Little Dream of Me]]</ref> She is later resurrected by [[Death]] and turns into a [[zombie]] and he has to kill her again,<ref name="five15">[[5.15 Dead Men Don't Wear Plaid]]</ref> which causes him more grief.
Bobby has known the Winchesters since at least the late 1908s. By 1989, John was leaving the boys in Bobby's care <ref>[[7.10 Death's Door]]</ref>. In 1991 -- , he gave an 8-year-old [[Sam]] an [[Dean's Amulet|amulet]] as a Christmas present for his father, which he eventually gave to [[Dean]].<ref name="three08">[[3.08 A Very Supernatural Christmas]]</ref>. Bobby also played catch with DeanOne at elast one occassion,<ref name="seven10" /> and he took the brothers deer hunting.<ref name="seven09">[[7.09 How to Win Friends and Influence Monsters]]</ref> [[John Winchester]] and Bobby were not necessarily on good terms -- Dean comments that the last time Bobby saw John he nearly "filled him with buckshot."<ref name="one22">[[1.22 Devil's Trap]]</ref> It is to Bobby's place that Sam and Dean go to grieve after John's death. After this Bobby's relationship with the Winchesters grows even closer, and he becomes both father figure and friend.
When Sam and Dean try to go after [[Lilith]] without him, Bobby tells them, "Family don't end with blood, boy."<ref name="three16">[[3.16 No Rest for the Wicked]]</ref> and more than once Dean tells Bobby he's like a father to him. Bobby has listed Dean as his official next of kin.<ref name="three10" /> In 2009, Bobby is paralyzed from the waist down after stabbing himself with [[Ruby's knife]] to overcome his own demonic possession when [[Meg]] orders him to kill Dean.
