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This essay is a work of comparative theology regarding the sociopolitical and moral dimensions of the idea of spiritual friendship. It specifically analyzes the points of connection between the spiritali amicitia of twelfth Cistercian monk Aelred of Rievaulx with the Kalyāṇa-mittatā of select Suttas from the Buddhist Pali canon. Both texts argue for the importance of friendship, particularly what they each call spiritual friendship, the highest form of friendship, for the holy and moral life. Such friendship subverts oppressive power structures, particularly legalistic static hierarchies, by catalyzing a new and just "relational hierarchy" in which spiritual friends serve one another as moral exemplars. The essay especially focuses on the way in which those with a higher station in life—socially, economically, politically, spiritually—invite into friendship those who are marginalized, which disrupts social orders intended to protect the wealthy and powerful that benefit by maintaining class distinctions. When these distinctions are undermined through spiritual friendship, the friends can find freedom, salvation, and enlightenment.