During the postmodern era, the concept of ‘absolute reality' has been replaced by the concept of ‘pluralism'. Reality in the postmodern works has been deliberately mystified to open the realm for an indefinite number of possibilities through subjective perception and interpretation. Possible Worlds Theory (PWT) is a postmodern theory that has an explanatory power in discovering the hidden layers of meanings in the work of fiction with their variable realities. Postmodern absurd drama is selected for this study because of its great potential of presenting works with no clear center and no fixed reality, leading to ambiguity which would be a rich medium for the application of PWT. Marie Laure Ryan is a literary scholar and critic whose possible worlds typologies and techniques will be applied to Miss Witherspoon (2005) by the American dramatist, Christopher Durang. The rationale behind choosing Durang's play is that it is one of Durang's most absurd plays which presents a rich field for PWT application. The purpose of this study is to apply Ryan's modal system of fictional worlds, the types of possible worlds, and the typology of accessibility relations to the postmodernist absurd play, Miss Witherspoon (2005), in an attempt to unravel the possible meanings and the variable reality projected in the text. The study also highlights the different types of conflict as approached by Ryan, occurring between the different worlds and its significance in creating multiple meanings and possible realities