In this paper the author compares Hong Kong filmmaker Johnnie To’s (杜琪峯) formal articulation of urban space in his internationally celebrated crime films with that in his locally popular romantic comedies. Drawing from recent scholarship on urban space in Hong Kong, Chinese, and broader East Asian cinema, he establishes that To’s films in both genres hinge on spatial relationships that are specific to rapidly forming metropolises. However, through close analyses of the crime films Expect the Unexpected (非常突然 Feichang turan, 1998) and Breaking News (大事件 Da shijian, 2004) and the romantic comedies Turn Left, Turn Right (向左走‧向右走 Xiangzuo zou, xiangyou zou, 2003) and Don't Go Breaking My Heart (單身男女 Danshen nannu, 2011), he contends that To’s crime films depict these spatial relationships within a framework of spatial continuity, while his romantic comedies do so within a framework of spatial fragmentation. These two frameworks play into the two genres’ separate dramatic needs: fatalistic confrontation for the crime films vs. delayed reconciliation in the romantic comedies. However, To uses these spatial frameworks within the two genres to explore the ways that urban design can either thwart or facilitate encounters between the inhabitants of a global city.