This chapter examines games, play, and playfulness in various contexts. Its central focus is on how gameplay has become accepted and common to the point of being ubiquitous, and play and playfulness in general are now ambient and all around us. At the same time, play is taking place in silos, where oftentimes there is little to no real contact with other players. This is reflected against Richard D. Duke’s 1974 idea of games as a future’s language which is able to create gestalt communication through its systemic nature. The chapter examines reasons for this and finds that while the potential exists even now, games and other playful activities are still likely to guide us to learn them as individual systems, not as communication tools. At the same time, people have learned to play also many systems other than games.