Inanimate Alice is a unique example of the effectiveness of electronic literature on young readers. In Portugal, the impact of this story and the way in which it proposes contact with the ecology of digital media justify the acknowledgement of its aesthetic merits in school education, where electronic works are still absent. However, the syllabus is not a closed system that prevents any approach to artistic works not listed in the official reading list, and is open to the inclusion of other texts. Avó e neto contra vento e areia (Grandmother and Grandson against Wind and Sand), a short story by Teolinda Gersão, is an excellent literary vehicle for facilitating that inclusion, through the thematic and symbolic dialogue that can be established with Inanimate Alice. This dialogue involved a pedagogic experiment in which Inanimate Alice was extensively read in close relation with Teolinda Gersão’s story. The report of the experiment shows several possibilities for joint exploration and use of these works.