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This is the first book of its kind to offer a sustained critique of contemporary psychoanalytic thought favoring relational, postmodern, and intersubjective perspectives, which largely define American psychoanalysis today. Conundrums turns an eye toward the philosophical underpinnings of contemporary theory; its theoretical relation to traditional psychoanalytic thought; clinical implications for therapeutic practice; political and ethical ramifications of contemporary praxis; and its intersection with points of consilience that emerge from these traditions. Central arguments and criticisms advanced throughout the book focus on operationally defining the key tenets of contemporary perspectives; the seduction and ambiguity of postmodernism; the question of selfhood and agency; illegitimate attacks on classical psychoanalysis; the role of therapeutic excess; contemporary psychoanalytic politics; and the question of consilience between psychoanalysis as a science versus psychoanalysis as part of the humanities. The historical criticisms against psychoanalysis are further explored in the context of the current philosophical-scientific binary that preoccupies the field.