The physical, as well as romantic, attraction of homosexual male youth and adults to their heterosexual counterparts is quite common, especially during adolescence, when the importance of peer group, consisting mainly of heterosexual male adolescents, plays a major role in youth rebellion. Heterosexual men continue to be objects of passion for homosexual men during adulthood, whereas studies consistently demonstrate the negative attitudes held by heterosexual men toward their homosexual counterparts. This article attempts to examine whether this attraction of gay to straight men merely expresses an admiration to the ideal of masculinity presented by straight men or also some difficulty to accept homosexual orientation and internalization of homophobia, typical to straight men. Anna Freud’s Identification with the Aggressor is the core defense mechanism of this discussion and its role in the attraction of gay men to their straight counterparts is psychoanalytically examined. It is suggested that understanding this mechanism consists an essential part of affirmative psychodynamic therapy, targeted at helping gay patients to peacefully accept their different sexual orientation. This challenge sharply contrasts the dark era of misusing psychoanalytic principles for the sake of pathologizing male homosexuality.