The chapter examines the concept of fun, specifically the contradiction that "serious" learning and positive affect, the fancy way of saying fun, are incompatible in and around the classroom. Despite the fact that pedagogies considered fun are often unique, highly interactive, and impactful; the fun descriptor is perceived as a badge of levity, thus limiting the useful application of otherwise effective educational approaches. This is a particular problem for those trying to help students develop their creative thinking identity and capacity, as well as those utilizing creativity to enhance learning. Lessons are drawn from research and practice on fun in work and educational settings, and numerous guidelines are provided for facilitating serious fun. [For the complete volume, "Creative Contradictions in Education: Cross Disciplinary Paradoxes and Perspectives. Creativity Theory and Action in Education. Volume 1," see ED612145.]