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The literary genre of fairy tales is globally recognised. Fairy tales are ancient tales shared amongst generations, a memorable feature of childhood to many. Fairy tales carry a social message, a reflection of the cultural values and norms of society and constructing what we refer to as idealised gender roles. This article is interested in the representation of women in fairy tales, giving particular focus to various adaptions of Hans Christian Andersen’s “The Little Mermaid”. This article analyses Andersen’s 1837 original along with Walt Disney’s 1989 animated adaption and Louise O’Neill’s 2018 reimagining The Surface Breaks. This article takes the two central female characters and focuses on how each text conforms to or resists hegemonic perspectives of femininity and gender roles. The article found that ideas surrounding gender roles and femininity have evolved over time, with earlier versions of the tale conforming to the tropes of the beauty ideal and O’Neill’s contemporary tale encouraging audiences to resist hegemonic perspectives.