This article explores how adolescent literature—here defined as literature about adolescents and not specifically for adolescents—from different centuries and different social/ religious communities enables adolescents to come to terms with the mysteries of the adult world, and more specifically, with the rules of that world based on the analysis of three Canadian novels—Anne of Green Gables, Anne of Avonlea and A Complicated Kindness, the first two by Lucy Maud Montgomery and the third by Miriam Toews. Having won considerable critical acclaim, these novels appeal to adolescents and adults alike by offering a timeless exploration of the concerns of the protagonists facing most adolescents, irrespective of their nationality, faith or philosophy.