In this paper, gender negotiations in the production, musical forms, and consumption of Cantopop are taken as a cultural exemplar for a social and political imagination of ambivalence, which seems to be shaping popular life in Hong Kong. It has three focal points -musical forms and expressions of Cantopop (style, lyrics, iconography, affect), gender politics, and 'everyday-ness' -which converge to mark a notable cultural logic performing an enlarging sense of ambivalence about a city that has seen a shift from high moments of economic prosperity to the current postcolonial uncertainties. In other words, Cantopop signals a shift in our sensibilities, a redrawing of our affective map of everyday life after an important historical and politico-administrative shift. In a sense then, this paper explores Hong Kong's changing identity within the sight and sound of popular culture, by specifically tracing some of the ways in which gender politics is inscribed, coded, negotiated, performed, or simply flirtingly posed on the surface of popular culture.