Contemporary practitioners of experiential learning look to John Dewey and other progressives for the foundation on which to interpret, design, and facilitate learning through experience. Although Dewey's theory of learning through experience was greatly influenced by other educational theorists and practitioners of the 18th and 19th centuries, by identifying parallels between Dewey's "experiential continuum" and Jean-Jacques Rousseau's model of educating/creating the ideal man in "Emile," a fascinating and troubling challenge to the role of the experiential educator surfaces. The purpose of this paper is to not only highlight the contemporary inheritance of experiential learning theory from Rousseau and Dewey, but to also invite educators who identify themselves as experiential learning practitioners to reflect upon their own experiential pedagogy. Current practitioners and leading proponents of experiential learning, like the National Society for Experiential Education, espouse an "intentional" and natural or "authentic" learning arrangement, with the essential role of the educator as designer and director of the student learning experience. Even though Dewey warns against the dangers of teacher imposition at the expense of student curiosity and independence, contemporary practitioners employing a facilitator-centric model could find themselves on the slippery slope of overcalculation and engineering, à la Rousseau's omnipresent tutor sharing a room with Emile. Thus, with the invitation to practitioners to reflect on their own roles and intents in designing experiential learning for students is included the consideration of Roberts's critical layer. Neutrality, like Rousseau's assumed "natural learning," is impossible to obtain, but recognition of and reflection on the structures which involve the learning arrangement itself could provide some element for the student to better understand his or her actions and the role of the educator facilitating the experience.