To fail to meet someone's hopes or expectations, leaving them feeling let down or sad.
From Old French 'desapointier,' combining the prefix 'des-' (meaning to undo) and 'apointier' (meaning to appoint or prepare). The word originally meant to remove from an appointed position, but shifted to mean failing to meet expectations.
The word 'disappoint' originally meant 'to remove someone from office,' but it evolved to mean 'to let someone down'—the metaphor shifted from being fired from a job to having your hopes fired away! Medieval bureaucracy gave us a modern emotional word.
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