This book defines and analyzes the elusive concept of cultural dialectic, as it ambiguously manifests itself in selected works of Ludwig Lewisohn and Cynthia Ozick. Taken separately, the terms «cultural» and «dialectic» each open onto a vast panorama of different – and sometimes competing – significances. Dialectic is understood to represent not the Western philosophical tradition of duality as opposites, but rather the Judaic dialectic, or pilpul, which describes a complementary webbing of consciousness and centerlessness. Lewisohn’s and Ozick’s works are viewed as unique examples of a complex mesh of Judaic, Western, European, American, and Gentile cultural determinants. A slippery confluence of contrasting characteristics, these writings are both autobiographically non-fictional and fictional; factually true, but also invented.