Etymology

fall between two stools

Today it means: To fit into neither of two categories and, hence, be neglected or fail. Full definition →

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The story

From an old proverb, "Between two stools, one falls to the ground", which dates from 1390. This, in turn, is most likely a translation of the medieval Latin proverb labitur enitens sellis herere duabus ("he falls trying to sit on two seats").

Etymology from Wiktionary, CC BY-SA 4.0.