This study presents an interchange of advice from Screwtape and Ignatius-the tug between Ignatian Spirituality’s two movements of the spirit, Consolation and Desolation, based on the Rules of Discernment found in the Spiritual Exercises. The dialogue between the master tempter and the master discerner is a concrete example of the interconnectedness of religion/spirituality and literature. Narrative Criticism, though originally pieced together for biblical studies, opens a wide path for the dialogue to happen. The pieces of advice of the two masters follow the structure of C.S. Lewis’ novel The Screwtape Letters. This exemplifies how consolation and desolation may happen in real life as it did in the patient’s life. Finally, this study shows that discernment is important for all Christians not only during life’s crossroads but more importantly in the choices of everyday living.