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When in 1460 Jacopo Antonio Marcello’s son Valerio died prematurely, various humanists sent consolatory writings to the Venetian nobleman. The most important of these was Francesco Filelfo’s Latin Consolatio ad Marcellum. The genre of consolation has always been characterized by oppositions. In my paper I will deal with the rhetorical aspect of the issue and discuss the ambiguous situation in Filelfo’s Consolatio. Filelfo not only disseminated his work, but he also used it to “sell himself” to potential new patrons. On the other hand, we can discern a very personal approach by an author who clearly also wanted to create an intimate relation with his main addressee. In order to demonstrate Filelfo’s difficult “balancing act”, I will compare the Consolatio with, among others, another of Filelfo’s writings, viz. the Oratio parentalis, and one of Petrarch’s Letters of Old Age, viz. Sen. 10.4.