This thesis focuses on the play-space as a realm of impossible desire in the novels Hopscotch and Lolita. Play-space, which I borrow from Johan Huizinga's Homo Ludens, is a space within which play can erect its own epistemological system that regulates the game and the players. These novels are concerned with the free play of language which subverts a stable discourse about how desire operates within the play-space of the novels. To this end, I will employ the Derridean sense of free-play (writing) that is decidedly the result of the loss of the "center" of structure that historically served to orient and limit the "play of the structure." Thus, free play destabilizes the discourse of desire in its use of various ludic linguistic elements, like the word game, in addition to how these novels play with genre and the form of the novel. Both novels are fundamentally concerned with how the written word constructs a puzzle-like world in which each of the narrators direct their own subjectivities towards objects of desire which they cannot ultimately possess. These objects (Lolita and La Maga) are themselves constructed by the playful language of the solipsistic narrators whose desire, finding no object to which to attach itself, turns in on itself and drives them mad. In these novels, the quest for lost lovers becomes a more important game than the actual act of sexual congress. The ecstasy of desire is not in sexual consummation but the pursuit of the infinite puzzle, the cryptic code of desire, that Humbert and Oliveira follow through the American (waste)land and the Franco-Argentine intellectual scene, respectively. By exploring the play-space as a realm of the free play of language, we are aided in our reading of these difficult postmodern texts as deconstructions of stable narratives of desire.