In this article, we present the Association Engine, a multimedia installation that explores the space of language and exposes connections between words. It externalizes meaningful associations to remind the viewer of forgotten connections but also introduce her to new ones. It accomplishes this by performing a series of improvisational games. It stands out from previous efforts in the realm of computers and theater as the agency has been empowered with a cultural understanding, more specifically, it uses the Web as a source of cultural reality.