This article is a study of the performativity and metaphoricity of desire and its corollary-anxiety-in Henry James's The Ambassadors. It examines the passage of Lambert Strether, the protagonist of the novel, to Europe as predominantly an exploration of the erotic, a conscious effort to delimit and to cross the boundary between self and other, with his eroticized and eroticizing speculation/specularization serving as the point of departure and penetration. However, encoded in the socio-political field of exchange, desire is also subject to the chain of displacements and deferments and, hence, only to partial fulfillment. Thus, rather than pursuing the thematic of the triumph of desiring imagination over reality in The Ambassadors as many Jamesian critics have done, this article examines the endless negotiation between the individual's desires and the dominant sexual ideology, focusing discussion on expenditure (restrictive or otherwise), sacrifice, and the theatricality of desire in the novel. The incessant dialectic between interdiction (in the form of the New England conscience) and its transgression both structures the novel's progress and maps out the itinerary of Strether's nomadic desire. This article concludes that Strether's specular/speculative economy denotes both the triumph and the defeat of his erotic imagination.