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This dissertation presents a thorough, line-by-line commentary of Ovid's Heroides 5, 16, and 17 (Oenone to Paris, Paris to Helen, and Helen to Paris) with an eye towards assisting the 3rd year high-school student or 3rd semester college student in translating and appreciating the grammatical, poetic, and allusory skill of Ovid, while still providing substantial textual discussion that will appeal to more advanced scholars. The introduction explains the theoretical and practical considerations which shaped the commentary, which takes an in-depth view of each couplet presenting the Latin lines of the subject poems along with ad loc. discussions on grammar, syntax, allusion, intertextuality, poetic structure, and character psychology. Additionally, literal translations, tables of mythological references and stylistic devices, as well as a brief discussion on the dating and sources of these poems are included. Through this multi-faceted approach to examining these poems, the reader is able to gain greater understanding of the complexity inherent in these elegiac epistles. The introductions to each poem and the introduction to the entire dissertation are meant to provide readers insight into the psychological profiles of the characters in question, particularly where they fit into the meta-literary traditions of epic and tragedy from which they are plucked. Special attention is paid to how these characters have been shaped by their past literary lives as well as by their new-found elegiac surroundings.