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Hans Vaihinger, the early 20th Century German philosopher, contended that across a broad range of thought people tend to select one theory over others, all the while knowing that such a singular perspective is but an idealization or useful fiction of what the fuller truth is if one eventually includes those other theories. He argued for the necessity of utilizing a plurality of perspectives in order to see a more complete picture of the world despite our cognitive inability to juggle more than one theory at the same time. This vexing paradox is a focus of the contemporary philosopher Kwame Anthony Appiah’s recent work that pays tribute to Vaihinger’s exploration of this topic. Appiah also examines Vaihinger’s view that hewing to a single fiction at certain times and for certain reasons is useful, while also considering how to expand one’s scope to reach for a more inclusive multiplicity of inexact models. I apply these and related issues to the psychoanalytic clinical situation, addressing such matters as: the possible triggers for the analyst’s shifts toward alternate theoretical persuasions and the complex matter of truth.