<p>Compassion is a fundamental component of social existence. However, in late modernity, several structural transformations undermine it. This article analyzes the paradox contemporary constellation characterized by the ‘inevitability’ and ‘impossibility’ of compassion. First, the general components of compassion – corporeal proximity (Zahavi), interaffective responsiveness (Rosan), and responsibility (Levinas) – are examined from a transcendental phenomenological viewpoint. Second, the late modern structural constraints of compassion – functionally and structurally differentiated roles (Goffman), rational, indifferent behavior patterns (Weber), and expert institutions of care (Castel) – are examined from a sociological perspective. Finally, the broader consequences of ‘inevitable’ yet ‘impossible’ compassion are examined by combining transcendental and sociological phenomenology. Although unambiguous compassion becomes improbable, substitute forms emerge. While these substitutes play an important role, they also contribute to the paradoxes surrounding contemporary compassion: by offering a compromising strategy, they normalize a narrowed, potentially amoral pattern of compassion.</p>