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“Empathy” has negative connotations for many legal theorists, who may conceive of it as subjective, lacking in intellectual rigor, and emphasizing sensitivity over reason. Even those legal scholars who have embraced the importance of empathy in legal work have emphasized its affective dimensions: pointing out that empathy is central to human relations and motivations, and is therefore a crucial lawyering skill. This paper builds on social science literature that identifies both cognitive and affective dimensions to empathy, and recasts empathy as in part a central component to higher-order thinking in law. It draws examples from empathetic reasoning in foundational cases in studied by most law graduates, then proceeds to map the empathetic thinking at work in a series of recent cases in which students have sued school districts for failing to prevent anti-gay harassment which allegedly interfered with their ability to receive an education.