• This work provides a close linguistic and thematic analysis of the dialogues in the two novels Midaq Alley by N. Mahfouz and Rosa Mistika by E. Kezilahabi, as they reflect fundamental assumptions about gender, tradition, and modernity. Certain complex clauses that have been traditionally recognized in Logic and Philosophy to be used in argument play a key role in expressing the conflicts that are central to the themes in both works. The data for this analysis come from dialogues and conversations found in the English translation of Midaq Alley and the Swahili of Rosa Mistika, specifically, simple conditionals, contrary-to-facts, and hypotheticals. The merger of Philosophy, Discourse Linguistics and Literature permits a close analysis of literature for cultural and thematic content. The pragmatic information imparted by these structures, such as speaker presuppositions, entailment, perceptions about possible fulfillment add much to the revealing of the themes that are central to the two novels: the urgent need for both societies to confront the roles of women in African societies, the tendency to favor modernity over tradition, and the implications of socio-economic inequality.