Over the past twenty years, the understanding of the potential of video games for learning has moved beyond early theorisations of games as entertaining providers of content knowledge to a general appreciation of the potential of good video games as active and constructivist problem-based learning environments with embedded mechanics that can motivate and encourage continued player engagement. However, playfulness as an attitude of mind and philosophy is under-considered in game studies. In this chapter I argue that play represents the juxtaposition of both games and playfulness, and highlight three educational affordances that are created through playfulness. These are: the creation of democratic play spaces; the importance of a willingness to enter a spirit of play; and the positioning of failure as positive. Video games normalise failure by design, while playful communities and attitudes provide the support and resilience to promote progressive failure. This is a crucial skill for students as they learn to take risks appropriately, step out of their comfort zones, and learn from inevitable mistake-making in the real world.