In this article, the authors use the O. Henry story Transients in Arcadia to illustrate how readers can make a text more meaningful by connecting it to themselves, to other texts, and to the world. Transients in Arcadia is a celebrated ironic commentary about the desire of everyday men and women to experience wealth. The authors have leveraged classic American short stories to explore how teachers working within a prescribed literature curriculum might take up new language and forms in participatory formats, visualize a storyline, and develop deep comprehension through layered question-making. In this article, they extend these discussions and underscore the value of the deliberate juxtaposition of readers' lived experiences with the text as the authors explore words and worlds -- especially ones that might initially seem antique, difficult, or even irrelevant to contemporary lifestyles.