Classical social theorists, including Marx, Weber and Simmel, often deem monetary mechanism as the supreme principle that universalizes the interchangeable relationship between person, object and social activity. Owing to the socially dis-embedded nature of modern money, accordingly, traditional social linkages have been exceedingly weakened and thus the social individual旧 ways of expressing affects are limited. While a few scholars have pointed out the ambivalent role that money may play in constructing unconventional sexual identities and life politics, in the field of queer studies investigations into everyday-life practices of monetary exchanges are generally overlooked. Based on materials of long-term orthographical research, this paper compares two generations of Taiwanese lesbians in terms of monetary practices, self-identity formations, and exercises of “in-circle” social ethics. It shows that the early 1990s generation had gradually imitated the monetary principle in adjudicating the values of intimacies, while the 1970s generation of “elderly tomboys” have practiced “delayed recognition” and “vicarious gratitude” continually over the past four decades. To conclude, this paper argues for a more historically and socially trenched understanding of queer everyday life politics. Following such a critical vein, the seemingly divergent ways of practicing intimacy through monetary and gift transactions between the two generations of lesbians may be attributed to the increasingly powerful political-economic mechanism of neo-liberalism over the past two decades.