Shannon Hale, Dean Hale, and Nathan Hale's graphic novel set "Rapunzel's Revenge" (2008) and "Calamity Jack" (2010) features fractured fairy tales that take up the issue of 'the damsel in distress,' questioning and complicating traditional gender roles in fairy tales. Throughout both graphic novels Rapunzel's character challenges traditional representations of being feminine within the heterosexual matrix (Butler, 2006). And, in many instances, Rapunzel does this by blending masculine and feminine traits, rather than trading one for the other. However, she also falls back into traditional fairy tale tropes that maintain boundaries around who women are and what they can do in these narratives. Because of the opposing narratives of femininity in these Rapunzel-influenced graphic novels, there were openings for seventh grade students reading these texts in their English Language Arts class to notice, critique, and question the texts and their messages. By exploring both the texts and students' responses to them in detail, this article focuses on textual tensions around gender representation that offer opportunities for young people to critique and analyze reading a "wonder tale." These young readers wondered and re-imagined how gender and femininity could be represented, not only in fairy tales, but also in their worlds beyond the text. Ultimately this article seeks to advocate for books that take up a more complex and fluid portrayal of what it means to be human and reading practices that support that complexity and fluidity.