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This paper examines the parapraxes made by, to or about Jewish-identified individuals discussed by Freud in Psychopathology of everyday life. Each of these errors and slips is occasioned by what he terms a ‘mésalliance’ between a Jew and a Gentile. Such incidents of distorted language betray unresolved ambivalences and unformulated anxieties endemic to Jewish-Gentile interaction in Freud's Vienna. First, the disturbed relationships between German-speaking Gentiles and their threatening Doppelgänger, the Jews, are analyzed by means of Freud's analysis of the ‘uncanny’ and an examination of the particular restrictions placed upon the ‘officially’ emancipated Jews in the Habsburg Empire, especially with regard to intermarriage. Then, the paper turns to Freud's discussions of explicitly Jewish-identified individuals and their limitation to illustrating parapraxes associated with what should be the most pleasurable and intimate relationships between Jew and Gentile, namely sexual and connubial relations. His focus upon this conflicted conjunction diagnosed the intrinsically problematic character of Jew-Gentile interaction in his Vienna.