This chapter argues that soliloquy as problem and opportunity was central to the aims of Latin love elegy, especially to Propertius’ Elegies. Drawing comparisons with the Lydia, Dirae, Tibullus’ elegies, Virgil’s tenth Eclogue, and Propertius’ elegiac predecessors, it studies Propertius’ corpus to demonstrate the relationship between the poet’s insanity and his solitude. It shows how seasonal indications inscribe this solitude in time and space, and how Propertius worked to rewrite love as a secret fiction. Propertius’ elegies, it argues, use solitude to shape the harmonization of elegiac subjectivity and the poets’ other political personae, culminating in the last of his elegies (4.11), which encapsulates the relegation of truth telling, love, and poetry to the solitary sphere, thus embodying new coordinations of public, the private, and the individual. In conclusion, it points to the impact of Propertius’ solitude on Renaissance literature, including the Hypnerotomachia Polyphili and Ben Jonson’s Poetaster.