In this essay, Sarah M. Fine explores the misalignment between instructional practices in secondary classrooms and the interests and capabilities of adolescent learners. Drawing on a series of ethnographic cases, she explores the potential consequences of this misalignment and attempts to conceptualize an alternate reality in which high school classrooms could become places where cognitive rigor and deep engagement function as mutually supportive priorities. Fine theorizes that a promising path forward would be pursuing instruction that involves intellectual playfulness--a construct that marries open-ended problem solving with opportunities for risk taking and flow. These same cases, however, illustrate that this pursuit would require profound transformations in the policies, practices, and perspectives that currently dominate the field.