While Hou Hsiao-Hsien has been celebrated primarily for his depictions of Taiwanese rural life, his films have also grappled with aspects of the urban experience, particularly in the latter part of his career. This paper examines metropolitan life in two of these more recent films, Millenium Mambo and Cafe Lumiere, with an eye towards drawing out continuities with Hou's own earlier films and with those of his contemporaries. The films form an interesting pair because each features a lonely young woman caught up in complicated personal relationships and struggling to find meaningful connections amidst the anonymity and confusion of urban life. While Mambo is set in Taipei and Cafe in Tokyo, both women travel between the two cities, underscoring at once the universality of the postmodern metropolitan experience and the specific historical connection between Taiwan and Japan. My analysis aims to focus on a number of areas: architecture and the alienating effects of urban spaces; the effect of technology on human relationships; the motif of travel and its emotional correlative—that restlessness that Raymond Williams identifies in “modern men and women who do not so much relate as pass each other and sometimes collide.” Finally, I hope to argue that, in both of these films, it is through historical awareness that the young urban-dwellers are able to find a sense of connectivity and purpose. It is this idea—that historical knowledge leads to redemption—that most strongly ties these later films to Hou's entire body of work.