Though nearly forgotten for three centuries, the poetry of the Elizabethan Jesuit martyr, St. Robert Southwell, was immensely popular and influential among his contemporary cross-confessional readers. No less surprising, so too were the works of St. Bernard of Clairvaux, which the missionary-poet requested “[or his solace” in the Tower. While most studies of Southwell mention this biographical fact, none examine its literary ramifications in any depth. In response, this essay explores Southwell’s and Bernard’s similar relations to their respective literary cultures, particularly in their religious conversion of the language of secular love. While better illuminating this central theme of both authors, this essay points to the Jesuit’s contemplative medieval heritage as well as the Cistercian’s early modern apostolate.