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This article shows how poetry and letters that Edmund Burke wrote to Richard Shackleton remain a testament to the young Burke's remarkably perverse reaction to heterosexual intercourse and marriage and give a moving record of his passion for Shackleton, a passion whose delight, intensity, heart-break, anxiety, jealousy, and masochism, exceeded the decorum of friendship as it was understood in eighteenth-century British culture. The article contextualizes Burke's passion for Dick in terms of the heritage of same-sex sworn friendships common in seventeenth-century English Catholic culture and proposes that this tradition is a useful context for understanding Burke given that he spent his boyhood among his mother's family, the Nagles of North Cork. We might read this up-bringing among the traditional society of the Catholic, Jacobite, crypto-aristocratic Nagles as resulting in the young Burke operating within a traditional understanding of same-sex sworn friendship that was out of step with the conception of what love meant and how it might be expressed between men in mid-eighteenth-century Britain. The shifting ground of male homosocial society of eighteenth-century Britain was increasingly more limited in expressions of love allowed between men.