The 1950s of Hong Kong manifests the initiation of a communal imagination oscillating in between the sovereignty of a British colony and the reality of a Chinese territory. The influx of immigrants from the north and, as a result, the establishment of a border during the 1950s not only restructured the demographic composition of the city but also brought along new momentum for mass cultural productions. Along the contestations and reconciliations between different ethnicities, languages, and identities, Hong Kong cultural configuration has since then embarked on a trajectory of its own, including the conceptualizations of childhood, border, and national ambiguity. Whether this piece of land was once desecrated by colonialism or this reclaimed territory is now alienated by renationalization, the formation of childhood serves as a critical lens to examine the meaning of border and nation from the colonial to the postcolonial eras of Hong Kong. Capitalizing on two titles produced in the early 1950s and in the late 1990s of Hong Kong cinema, namely, Fung Fung'sThe Kid(1950) and Fruit Chan'sLittle Cheung(1999), this article aims to explore the correlation between border, community, and nationality through the life adventures of the child protagonists, whose transitions and explorations are entangled with a political and territorial border that polarizes our sinophonic imagination in the ongoing present of China-Hong Kong division. In this context, the cultural configuration of Bildungsroman, apart from manifesting Franco Moretti's "the symbolic form of modernity" or Marc Redfield's "acculturation of the self," should embody the struggles with an obscure nationality, as here exemplified from the footprints of childhood tiptoeing on and off the borders of Hong Kong.