The discussion herein is guided by questions "asked" and responses "given" seemingly in one sitting. However, this is a façade. All responses are direct quotations from the published scholarly writings and unpublished archives of George and Annemarie Roeper. This is a conversation taking place somewhere in time, prompted by Robert Schultz's wanting to honor the Roepers in this celebratory journal by sharing some of their most poignant and insightful thoughts about City and Country School (The Roeper School) and their lives in service of the students, families, staff, and faculty who work there. All of the responses to guiding questions cross expanses of time--and should be recognized as culturally and socially bound to the period from which they were compiled and/or written. The responses illustrate the Roepers' forward thinking as documented in their discussions, writings, and presentations.