This dissertation examines Dante's ideas on emotions or affects, and the literary, moral, and spiritual significance of affectivity in his writings— in the Commedia and the Vita nova—in the context of medieval affective piety. I focus on the pilgrim-protagonist's key affects and affective states, such as fear (paura), grief (dolore) and sorrow (tristizia), and study his inner affective growth and transformation, i.e., the education of affects the pilgrim-protagonist receives and showcases.As I demonstrate, in conversation with the tradition of affective piety in his own stories of salvation and redemption, Dante brings important thinkers of affective piety—Augustine, Anselm, Bernard, Aquinas, and Bonaventure—onto stage in the Commedia as characters, who, with their life stories full of affections, and with their expressed affections towards each other and towards the pilgrim, teach Dante about affection and faith. The affections that the pilgrim experiences in his spiritual journey—fear, sorrow and eventually joy—are a participation in Christ's affections on the Cross, and the remembrance of God's love for us. All the guides that Dante has in the Commedia bear the grace of Christ, and are, together as an "affective community," a testimony of God's love. All the affective relationships the pilgrim has formed in his journey, with his relationships to Virgil and Beatrice as the center of focus, are ultimately his encounter with Christ's love.