In this essay, I relate my experience of teaching an upper-division class on romantic poetry—my struggles, assumptions and discoveries, and my ultimate decision to revise the way I teach, and to some extend think about, romanticism. The problem—the contemporary/romantic opposition (the topic of this volume of essays)—turned out to be a pedagogical and critical opportunity. It also became a way for my students and me to think and talk about an even deeper split, the schism between the values of our contemporary culture (including the culture of an increasingly professionalized and professionalizing academia) and those of an “aesthetic education.” In what follows, I give firsthand reports about what worked and what didn’t in a class that came to be called “Repetitions of the Romantic,” an engagement with romantic and post-romantic art. Along the way, I address some methodological problems, and offer some reflections on the fragility of teaching the humanities in the contemporary classroom and more specifically on what I see to be the challenges and benefits of teaching the romantic within specific contexts, in my case within the economic and social micro-culture of central Ohio.