In God, Sexuality, and the Self: An Essay ‘On the Trinity’, Sarah Coakley rehabilitates desire as central to both divine and human ontology, and the reordering of desire as the key to human flourishing. Coakley presses a broad understanding of desire, against its Freudian reduction to sexual desire and against Anders Nygren’s sharp opposition between eros and agape. This paper brings Coakley’s work into dialogue with the work of Bernard of Clairvaux, drawing on his treatise On Loving God and his magnum opus Sermons on the Song of Songs. Bernard offers a nuanced understanding of desire and its reordering, underpinned by a realistic, yet optimistic, theological anthropology and a deeply scriptural, Trinitarian understanding the operation of the Holy Spirit in human life. For both Bernard and Coakley ascetic practice, especially prayer, underpins the transformation or reordering of desire, and helps guard against the misuse of the charismatic gifts of the Spirit. When graciously drawn into the life of God, desire is liberated from obsessive self-concern and reoriented toward loving concern for the other: God’s desire becomes our desire.