This thesis offers an intratextual reading of Ovid's Heroides 5 and 16-17, in which he reimagines the mythological love triangle between Oenone, Paris, and Helen in epistolary form. The three letters portray Paris's attempt to seduce Helen and convince her to elope with him, Helen's impassioned counterargument despite her physical attraction to Paris, and Oenone's efforts to win Paris back after watching him return to Troy with Helen. The Heroides, as a collection of elegiac letters, respond to generic features of Roman love elegy. This thesis focuses on one such elegiac convention— the use of exempla, references to mythological or historical figures who provide a model or precedent for specific behaviors. It argues that the letters of Oenone, Paris, and Helen participate in a debate about the use of exempla in elegiac rhetoric and even question exemplarity, the conventional elegiac strategy of reliance on exempla. Chapter 1 demonstrates that Paris (Her. 16) follows elegiac convention in using exempla to support his argument, but fails to address the additional patterns of his exempla that weaken his argument. Chapter 2 shows that Oenone (Her. 5), although struggling to insert herself into Paris and Helen's discourse, still engages with exempla more critically in her attempt to correct Paris's poorly chosen exempla. Chapter 3 examines Helen's rhetorically impressive response to Paris (Her. 17). Unconvinced by his argument and his exempla, Helen rejects exemplarity itself as a rhetorical strategy. I conclude that the intratextual discourse between these three letters critiques elegy's reliance on exempla and even questions the efficacy of rhetoric itself.