This article uses the methodology of Law and Literature to explore a number of themes in Restorative Justice for Juveniles. It draws upon Mark Twain’s The Adventures of Tom Sawyer and a number of Kate Chopin’s stories from her collection A Night in Acadie. This study examines literary representations of how children and young peoples grow to develop a sense of justice through experience The aim of this study is to raise a question about whether, in our attempts to develop Restorative Justice for Juveniles, we have fully taken into account the way in which children and young people make sense of justice in the context of their experience and their own agendas as developing human beings. It argues that their senses of justice, and how justice fits into their worldviews, ought to be perplexing to adults, and that what adults impose or suggest as possible fair solutions, can be paradoxically undermined, or have unforeseen consequences. Above all, however, we see in these tales the transformatory power of positive and negative relationships.