There is usually an agenda behind the rewriting of history. As an acclaimed Hong Kong director, Wong Kar-wai has made several nostalgic films set in 1960s Hong Kong, namely, Days of Being Wild (1990), In the Mood for Love (2000), and 2046 (2004). Relating to Hong Kongers’ anxiety over the 1997 handover, Wong’s films are part of a wider symptomatic cultural phenomenon in Hong Kong cinema. In his nostalgic films, time is often spatialized. With his constant interest in mobile space, such as hotels and trains, he creates an alternative perspective to question the grand narrative of history. In his reconstruction of the past, there is never any cultural purity or origin to revisit. Rather, the past is presented with itinerant characters, mobile space, and cultural ambivalence, enabling multiple narratives of history. Focusing on the use of space, this paper analyzes how Wong’s films engender a reflective form of nostalgia, and challenge both official history and the linear concept of time. Wong’s nostalgia, I argue, is not only a response to Hong Kong politics, but also a paradigmatic text illustrating nostalgic writing’s resistance to official historical discourses.