This essay aims at finding a clue to answer the following question: Is Stephen Dedalus a misogynist? Stephen’s position toward Irish women is discussable against two premises. First, he surely falls into the pitfall of the binary opposition of virgin and harlot deduced from Catholicism, even though he consciously challenges it. Secondly, the tawdriness of his circumstantial reality in contrast with the idealized romantic view of women has a poignant significance to Joyce’s whole scheme. Stephen’s problematic thoughts on the woman question render his ambitious project of being a national writer questionable mainly due to Stephen’s self-centered ego. The narrator’s distance from the would-be young artist’s questionable position toward Irish women thus deserves our attention. The binary logic of the romantic ideal and sordid reality, plus Stephen’s tilt toward his dream typically appear in his perception of Irish women. The female characters are fairly two dimensional in Stephen’s thoughts. They are either perceived as threatening or enchanting, seductive or aloof. Their fictional portraits are largely contingent on Stephen’s narcissistic projections and misogynist frame of mind. Stephen’s resort to the dark slimy streets of Nighttown and his sexual affairs with prostitutes lead him to a troubled initiation into the question of sexuality. His submission to sexual desire brings about a sinful feeling in him. His religious education is instrumental in enforcing his sinful feeling. The female characters have their own individualities and voices in Stephen Hero. This marks a crucial difference between Stephen Hero and A Portrait. In A Portrait the female characters appear only as the social types who are deprived of their own individualities, which reflects Irish men’s general attitude toward the opposite sex. Women do not interest Irishmen except as streetwalkers or housekeepers. Stephen’s relationship with Emma is no exception. Stephen’s self-imposed exile at the end of A Portrait is thus risky in falling short of a real freedom from the soul-stifling Irish reality if he does not pay due attention to his contemporary Irish people, especially Irish women.