This article discusses a set of tasks that introduce dilations using nonstandard figures, incorporating snippets of classroom conversations as students try to make sense of the specified tasks, to show how they progress in their understanding. The authors provide a theoretical foundation for the tasks and discuss the pedagogical implications for developing geometric proportional reasoning in students, where visual and spatial senses are invoked. The entire three-task set illustrates a learning trajectory that builds foundational understanding of similarity and congruence.