To create puzzles, quizzes, and uncertainty, James Joyce incorporated ambiguities into his writings, even in one of his best-known short stories, "The Boarding House." In this paper, a teaching framework for the story will be suggested for both the literary field and the English education field, with such textual ambiguities working as the backbone. Until now, relatively few studies have been conducted on how to teach Joyce`s works in a university setting. The class can be begun with a discussion topic, "Should Mr. Doran marry Polly or run away?"-a question that students are asked several times while reading the story in class. Motivated by such a controversial issue, students will explore the relationship between Mr. Doran and Polly based on evidence from the text. It is found that they had sexual relations and that Polly may be pregnant, despite a lack of definite evidence. The latter issue is explored further in Ulysses. Though the narrator in "Cyclops" said that Mr. Doran had been forced to marry Polly because of her pregnancy, his statement cannot be accepted as truth because he was not a trustworthy narrator. Through textual ambiguities Joyce tried to demonstrate that we cannot reach the truth, a proposition he shared with both philosophers and scientists at the beginning of the twentieth century. When students are encouraged to explore how he used textual ambiguities, they can actively participate in lively discussions in order to expose undiscovered meanings of his writerly text.