This article is an inter-textual study of the play Angels in America (Part One), Pope Francis’ Apostolic Exhortation Gaudete et Exsultate and key Catholic writings on homosexuality. I hope to show how the play might inform future Catholic understandings of self-identity, self-acceptance and self-love and how in turn, Catholic writings on the nature of love, sexuality and holiness can assist audiences to understand more deeply the themes and dilemmas in the play. The Catholic Church is immensely forgiving of the human failure to live up to the lofty demands of love and has a strong tradition of asceticism concerning the positive and transformative effects of self-control. However, due to the cognitive dissonance set up by its teaching on homosexuality, and in particular, its claim that there is an incompatibility between gay identity and ordained priestly identity, the Church has tended to retreat into a world of silence about the importance of self-knowledge to assuage the dissonance it feels. The dramatic deleterious consequences seen in the play about the failure to love oneself are a stark warning to the Church that this might not be the best or most pastoral path to take.