In The History of the Life and Adventures of Mr. Anderson (1754), Edward Kimber’s attempt to revision American heteropatriarchy plantocracy into enlightened patriarchism is founded on his ideological belief in enlightenment and Man of feeling. The pedagogical function of the fiction is to encourage masters to initiate pre-paternalistic ideas in the early modern Chesapeake region plantations. Also, it instructs and manages the emotions of women, servants, and slaves through involuntary subjection disguised as voluntary servile love and reciprocal intimacy. Enlightened patriarchism of The History serves as a means of increasing productivity and fortifying nationalism as it stresses the return profit of the master’s generosity and the potential threats caused by the rebellion of slaves and composes a narrative of a contented slave. Man of feeling, who claims his unsight authenticity and authority, not only preoccupies the political public affairs as a male preserve but also reclaims a feminine virtue as a male possession. This sentimental man is a product and evidence of sociability, sensibility, and civilization, and creates relations and connections based on his principles. The science of Man/manners in the eighteenth century employs an experimental approach through sensibility and effeminacy’s contribution to the early modern experimentation with masculinity. Man’s own circular sensibility and its shadowy other are used to draw a boundary that divides cultural climate through the coercive identification and paradoxically remaining difference.