In this talk I will examine how the play-element of videogames is deconstructed to try to bring fun back to real life. Games are reality-broken technologies in the sense that they are rule-bound elements that constraint action. Videogames are game-mediated technologies that take advantage of ICT to create more compelling user experiences. Two modern approaches, gamification and playful design, extract the constituent elements of videogames and take them to other non-game contexts to engage users and motivate action. Examples as well as theoretical approaches from game theory and the psychology of motivation will be presented to conceptualize this new level of brokenness. I will argue that this new attempt to bring fun back to everyday activities reflects an underlying brokenness in reality. This new framework addresses the multistability of game technologies and reality.