This dissertation explores the dynamic interplay between games and literature in China from the sixteenth to the eighteenth century, and how this interplay worked towards a definition of the “ludic” during a period of technological, cultural, and political transformations. This was a moment when authors became game designers, inviting readers to engage in various games of reading. With printed books as their primary game consoles, the early modern public learned to critically perceive and navigate a world full of chance, uncertainty, and instability.The concept of “reading games” is concerned with how specific game elements and logics are integrated into literary experiments in forms, narrative structures, and reading mechanisms, hence “gamifying” literature. It also serves as a heuristic approach to uncover an alternative history of reading by shifting the focus from the specific social groups of readers to the interactive, rule-bound modalities of reading that extend mere textual interpretations. Chapter 1 establishes the foundation of the dissertation by emphasizing “play” as a critical approach to defamiliarize the common reading experience and as a research method. Readers were asked to experience how a gamified text unsettled linear reading and challenged direct textual interpretation. Play also allows us scholars to use the accessible archives to discover the hidden rules, learn the design mechanisms of the reading games, and actively participate in enacting them. The remaining three chapters investigate the thinking, making, and playing of three types of “reading games”: reading puzzles, gambling, and riddling. Reading puzzles (chapter 2) require the reader to follow a complex non-linear trajectory of words to successfully figure out a poem, a lyric, or a song. This trajectory delineates graphic and formal-level innovations made possible by the creative perception and application of the Chinese writing system and its material substrate. Turning from words to narratives, gambling (chapter 3) highlights the episodic structure of certain short stories. Within this framework in which ordinary life intertwines with extraordinary events, the authors developed a new model of causality to link separate, usually unpredictable, incidents together. By experiencing episodic randomness akin to gambling games, the reader is trained to comprehend the implications of chance in relation to fate and contingency. Riddling (chapter 4), the last reading game, extends from the page to the stage. Riddles, as literary games, demand that the reader delve beneath the textual surface and decipher the concealed meanings. Their appropriation by the theater highlights how characters “guess” or “think” of a meaningful answer by connecting textual, gestural, or object fragments according to a certain logic. In doing so, playwrights invited the reader/audience to contemplate these interpretive mechanisms per se, especially how subjects would employ them to perceive the phenomenal world. Together, this dissertation demonstrates that in early modern China, people thought like game designers gamed creatively with the affordances of literature to develop a distinct epistemological perspective for viewing, understanding, and coping with reality. Overcoming the temporal distance, the notion of “reading games” enables us to join the historical players and experience with them these ludic endeavors.