While the world around him declines, Stephen's own sensitivities become more acute. In particular, we see the development of his attitude toward literature. Just as Stephen identifies with the protagonist of the children's story that his father reads to him at the beginning of the novel, he now imagines himself as the Count of Monte Cristo. These two experiences of reading show how Stephen's identification with a literary character shapes his perceptions of himself. Unlike the young boy in the children's story, Stephen's new role model, the count, is active, adventurous, heroic, and even somewhat dangerous. Like the count, who is a pursuer of vengeance and a righter of wrongs, Stephen is frustrated with the unfairness he sees in the world. In showing these relationships that Stephen forges with literary characters, Joyce implies that literature is not necessarily a solitary pursuit. Indeed, Stephen's friendship with Aubrey Mills is largely based on a shared passion for imitating Dumas's novel. Literature also helps guide Stephen's newly burgeoning sexuality, which he is able to channel into dreams of pursuing Mercédès, the heroine of The Count of Monte Cristo. Stephen finds romantic models in literature again when he uses a love verse by Lord Byron as a model for the poem he writes to E. C., the girl after whom he lusts at the birthday party. The intertwining of life and literature foreshadows the later ways in which the "Artist" and the "Young Man" of the title—one who creates art, and another who lives life—complement and reinforce each other.

Stephen's love interests develop in a complex manner. He experiences a tension between his somewhat awkward real-life erotic encounters and his idealized vision of gallantly pursuing Mercédès, the heroine of Dumas's novel. Yet Stephen's vision of ideal love is less a desire for a perfect love object than a hope of possessing a woman. The Count of Monte Cristo, on whom Stephen models his own idea of love, ultimately rebuffs Mercédès with the pithy rejection, "Madam, I never eat muscatel grapes." Stephen's fantasy, then, is not one of a love-filled romance, but one of repudiating a woman who desires him. The ambivalent nature of Stephen's desire manifests itself again when he stares, smitten, at a girl at a party, but then lets nothing come of it. Indeed, while he is staring, Stephen actually contemplates not the girl at the party but his first crush, Eileen Vance, whom he had watched years before. Unlike that of a traditional romantic hero, Stephen's desire for women is jumbled and confusing.