Calling attention to the Ovidian contours of Isabella Whitney's cursus litterarum, this essay reconsiders the literary heritage of the personae she adopts in The Copy of a Letter (c. 1566) and A Sweet Nosgay (1573). Existing analyses of Whitney's Ovidianism have tended to emphasize her debts to the female-voiced epistles of the Heroides while simultaneously overlooking profound intertextual connections between A Sweet Nosgay and Ovid's exilic writings. In contrast, this essay argues that the outlines of a self-consciously classical career trajectory (its stages demarcated by Whitney's subtle aesthetic shift from Heroidean amatory complaint to Tristian exile complaint) can be detected when The Copy of a Letter and A Sweet Nosgay are read contiguously.