The goal of this study is to contribute to the ongoing discourse surrounding speciesism by extending the questioning of human centrality into how fairy tales are retold. It is critical to examine and problematize the depiction of human-animal relationship in fiction—especially in fairy tales where animal characters, symbolisms and imageries abound—because it is in these fictional representations that humans encounter animals more frequently. Using concepts from posthumanism, Human-Animal Studies, and Fairy Tale Studies, retellings of “Little Red Riding Hood,” “Goldilocks and the Three Bears,” and “Jack and the Beanstalk” from Terri Windling and Ellen Datlow’s six-book anthology series of fairy tales retold for adults are examined in order to find out how these stories blur the boundaries separating the human from the animal. Fairy tale retellings intended for adults offer a much more complex interpretation of human-animal relationality that thrives in interconnectedness rather than in one-sided dependency. These retellings blur the human-animal boundaries by reconfiguring how human and animal characters are depicted, and/or by fusing them together creating a kind of hybridity that denaturalizes the categorical distinctions humans use to separate themselves from the animal and lays bare the constructedness of these boundaries.