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John Cheever's Shady Hill short stories explore the psychological paradoxes of American middle-class suburbanites epitomized by their indefinable inner pain ironically exuding from their perfect safety and happiness. This paper first discusses the equivocal narrative voice which Cheever has adopted to express the aesthetic and moral discontinuity between the facade, the back, and the inside of the life in the American suburbia, a so-called bourgeois Utopia. Such an equivocal narrative voice enables him to effectively express his sympathetic satire on the American suburbs. Then I try to describe the psychological middle-landscape of the suburban dwellers by focusing on their premature self-compromise and feeble selfhood which in turn cause their paradoxical pursuit of happiness. The suburbanites' strong desire for the ease of life motivates them to move into the suburb. Ironically, however, their psychological misery is chiefly engendered by their excessive concern for their own safety and happiness. Such a self-centered pursuit of wellbeing depending on their other-directed conformity of attitude reflects their feeble self which lacks some internalized principles for their acts. The American middle-class, mostly composed of self-made men, have chosen the suburb for their dwelling environment, a middle ground between a metropolis and rural area. They intend, on the one hand, to escape from the struggles and troubles of urban life and, on the other, to secure the harmony and relief of life under the influence of nature by deciding to live in the suburb. Never completely removing their life from the material wealth of a big city nearby, they seem to secure a perfect golden medium for their dwelling environment between nature and culture. In that sense, the suburb as a geographical middle landscape incarnates an ideal space for dwelling. In terms of their social status, the middle-class occupy a middle ground between the lower working-class below and the higher upper-class above. Reflecting such a socio-economical position of them, they indeed tend to show an eclectic attitude of life between the stimulation and the repose in it. Such an eclecticism of them, however, entails some serious emotional problems in the psychological middle landscape of the middle-class suburbanites. Hence their serious self-contradictions and terrible feeling of anxiety and hollowness.