In this thesis, I trace the development of confession in James Joyce. From A Portrait of The Artist as a Young Man to “Circe” and “Penelope” in Ulysses, Joyce’s model of confession works to forward characters' capacity for community, intimacy, and art, an ethical and artistic approach to art. The framework for confession in Joyce is introduced via depictions of the Catholic Sacrament in A Portrait, albeit its function is maintained even as it develops in “Circe” as a secular, psychoanalytical, and legal expression. It is in “Penelope” where confession transforms into profession in Molly’s monologue and in the way it serves as a theory of art for Joyce. The body, its transgressive role in desire and sex, its private functions, and its inextricable capacity for both life and death, remains the site of guilt and shame for Joyce’s characters. Instead of a perpetual cycle of sin, self-reproach, and confession, Joyce offers an alternative in which an affirmation of the body and its functions, modelled by Molly, can alleviate the guilt that proves so debilitating for Bloom and Stephen. By transforming confession into profession, Joyces offers a promise of reconciliation: a potential homecoming for the exiled Stephen and Bloom, a restoration of intimacy and relationship for son, father, and husband, and, finally, the possibility of genuine creativity is offered. This reconciliation enables, in the end, a remedy for impotence, and, as typified by Molly’s monologue in “Penelope,” guiltless expressions of, and foundations for, intimacy and art.