While most of the work on friendship in literature emphasizes the philosophical ideal of amicitia, usually focusing on the literature produced in a single country, 'Las amistades imperfectas' brings to the fore the changing literary representations of the tale of the two friends in a larger European frame. The devoted pair of 'amici' undergoes a dramatic transformation (between Boccaccio and Hobbes), from the metaphor of idealized aristocratic life and rule to a display of egoistic and vile shortcomings. As a key point of this evolution, this work analyzes the frustrations experienced from within the aristocratic patronage system by authors such as Cervantes, Lope de Vega and María de Zayas. Changes in social structures altered the lifestyles of writers; the author became more a professional and less a creature of courtly life and pomp. The existence of a larger network meant that authors could choose for whom they wrote or, at least, that they could have different sources of income. The need to maintain absolute fidelity to one patron in order to survive was rapidly disappearing, freeing artists from the restrictive rhetoric of loyalty in patronage-friendship relationships. This evolution affected the nature of friendship between artists and patrons, and the literary story of the two friends evolved from the exaltation of male 'amicitia' into depictions of the depraved exploitation of the other. This evolution can be seen in the work of Cervantes ('Galatea, La Numancia, Don Quijote, Persiles'), where the topos of the two friends reflects social changes as experienced by authors within the aristocratic patronage system. The issue of gender is fundamental to the tale of the two friends. María de Zayas, 'La traición en la amistad', rejects the social model of aristocratic male bonding as an environment hostile to women, showing instead an alliance among three women of different social classes as a more efficient and satisfactory model. I incorporate the work of Christine de Pizan, Giulia Bigolina, Margarite de Navarre, Isabella Andreini, Maddalena Campiglia, Moderata Fonte and Ana Caro into my analysis of Zayas. (Juan Gil-Osle)