The thematization of the change in socio-cultural patterns as a result of urbanization is explored in many of Tsai Ming-Liang’s films. Tsai’s films often deal with urban alienation of a society in which people are emotionally blocked and seemingly afloat in a state of loss. A broader cultural discourse is provided through Tsai’s foregrounding of Taipei, which imparts a sexual connotation to modern people’s relationships, leading to the exploration of the collapse of conservative categories of sexual identity in modern society. Homosexuality, especially, has been coded primarily in Tsai’s films as a resistance to patriarchal constructions of sexual relations and a transcending of its repressive categories. In placing Tsai’s films within the discourse of homosexuality, I-fen Wu suggests homosexual desire, is not only a resistance to patriarchal disciplines, but contains a sense of fantasy and identification that projects manly role models as ego ideals. This essay intends to discuss the leading character’s pleasures and threats gained from looking at “male” figures on the screen, and the recognition of self in the male image, exploiting the viewer’s desire to identify with the person(s) that he sees as being similar to himself. Wu explores the concept of, “looking” itself in Tsai’s films as not just a pleasure or recognition of self but as a “dialogue of gaze.”