I propose to reverse the prevailing understanding of the novel's concluding episode, "Penelope," as affirming and optimistic, and instead situate it as the wellspring of Modernist nostalgia. This darker reading of Molly Bloom's nostalgic reverie depends, as we will see, upon Molly's resonant psychological ties to her mythological antecedent: Homer's Penelope. Despite Molly's manipulative, contradictory, and at times self-deceptive consciousness, scholars still tend to read her famous final utterance as one of firm affirmation. Taking into consideration her semblance to Homer's Penelope, Molly's final "Yes" is likely less sanguine than previously considered. And even my own "reading" may confine her role too narrowly. Nevertheless, we should establish this countersign as a means of exploring the consequences of her nostalgic reverie.