In an expressivist culture, effective engagement must acknowledge teenagers' freedom to choose their own spiritual path. Yet, in an evangelical theology, faithful formation must hold on to biblical authority. As we seek to engage young people with the Bible, key questions need to be explored. Such questions include: how can pedagogical freedom be affirmed without undermining theological authority; and how can authority be asserted without diminishing personal freedom? This study explores a freedom-authority dialectic in theological dialogue with the educational philosophy of Maxine Greene. Greene's reflection on the arts and the imagination are brought into conversation with insights from Charles Taylor, Garret Green, and Nicholas Wolterstorff. As a work of practical theology, the book concludes with a framework to shape the purpose, content, and values for Bible engagement in contemporary youth ministry.