Serving as a theoretical jumping-off point, this chapter explores theories of play, to the end of relating the concept to gameful L2TL. It starts by focusing on the elements of the definition of play, noting that an absolute definition may be problematic because it does not account for the subjective nature of the experience. It then explores the concept of language play, an important notion for gameful L2TL because of its relationship to development and language awareness. It then explores the work of Roger Caillois, a philosopher of play who argued there were different types: ludus, paidia, agon, alea, mimicry, and ilinx. Each is related to gameful L2TL, to digital gameplay styles, and ultimately to L2 learning styles, which leads to discussion of motivation and whether and how different play and learning styles be accounted for in gameful L2TL practice.