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Due to the Winchesters killing the original [[Death]], Billie held a grudge against them, and in their first meeting told Sam in no uncertain terms that she intended to send Sam and Dean to [[the Empty]] when they died to ensure that they could never return.<ref name="eleven02">[[11.02 Form and Void]]</ref> While Billie couldn't kill the Winchesters herself due to the rules, she eagerly awaited her chance when they died or needed her help to be able to reap them.
Despite her stern and uncompromising demeanor, Billie is not unsympathetic to the suffering of others. When she attempted to reap [[Mary Winchester]] at [[Asa Fox]]'s funeral, Billie brought up how much Mary was suffering due to being resurrected after over thirty -three years dead and offered her peace. When Mary refused, Billie offered that if any of the Winchesters wanted a final peace, they could call her to reap them.<ref name="twelve06">[[12.06 Celebrating the Life of Asa Fox]]</ref> Later, while she refused to resurrect [[Crowley]] for Rowena, Billie expressed sympathy and understanding for the witch's suffering and attempted to help Rowena find peace in her loss.<ref name="thirteen19">[[13.19 Funeralia]]</ref>
After becoming Death, Billie gained a greater understanding of the universe and everyone's place in it. While openly admitting she was still not a fan of the Winchesters, Billie was reluctantly forced to acknowledge that they had a greater role to play than she would like. As a result, Billie resurrected Dean herself when he died, but was intrigued to note how much Dean had changed, particularly when he offered Billie a selfless deal in exchange for information, one that she took without hesitation. Billie also took the time to offer Dean insight into her role as Death and what she had learned since they last met.<ref name="thirteen05">[[13.05 Advanced Thanatology]]</ref>
A major aspect of Billie's personality as both a reaper and Death and is her uncompromising stance on the rules of the universe. The reaper [[Jessica (Reaper)|Jessica]] even pointed out at one point that Billie is all about the rules and was clearly unwilling to cross Billie by breaking them.<ref name="thirteen19" /> Billie's biggest rules are "what lives, dies,"<ref name="eleven02" /> and "no direct interference." Even when Rowena started changing people's fates, Billie refused to directly interfere or let her reapers get involved, only sending Jessica to act as a resource for Sam and Dean. As a result, Jessica refused to do anything at all to help beyond give information, even when Dean was in danger.
Despite her stance on the rules, it's indicated that over time Billie has become somewhat less uncompromising, at least in very serious situations. [[God]] at one point comments that Billie is always "sticking her scythe in where it doesn't belong."<ref name="fourteen20">[[14.20 Moriah]]</ref> Due to the threat from the [[Apocalypse World]] [[Michael (Apocalypse World)|Michael]], Billie directly interfered by rescuing the Winchesters, Castiel, and Jack from the grasp of [[Michael's Monsters]], something she called "a calculated risk." With all but one version of Dean's fate showing Michael taking him over and using Dean to destroy the world, Billie passed Dean the information he would need to avert that, but left it up to Dean whether or not to use what she gave him.<ref name="fourteen10" />
