This article examines diaspora in the context of intimacy in order to focus on individual conditions of art-making, taking into account global conceptions of diaspora that have appealed to celebratory, emancipatory, pessimistic, or desirous formulations about diaspora and art. Through a discussion of paintings by Himan Sŏk, a Chinese Korean (Chosŏnjok), and Jun Ch’ae, a Japanese Korean (Zainichi), the author proposes that diasporic art can be analyzed in terms of the transpersonal relations that surround the intimate vicinity of the artwork in three ways. First, these works of art are neither structured from above nor resistant from below. Second, they express an idea of doubleness bound at once to a larger organizing collective and to the individual experience. These artists imbue their paintings with ethnos and nation and the personal and intimate, and a comparison of their works reveals social relations that form around the objects and evolve as art is produced, exhibited, written about, and discussed. Third, transpersonal relations surrounding the artists and artwork underscore a two-tiered idea of who transindividuals are to others and to themselves, a concept of identity that is especially pertinent to diasporic artists who are postcolonial subjects, as it allows for differing “selves” according to context-specific settings. The transindividual is, thus, shown to be a critical concept of integration in understanding identity. Keywords: Chosŏnjok, Zainichi, diaspora, art, intimacy, transindividuality