This idiom describes failing to achieve either of two desirable outcomes due to indecision, compromise, or poor positioning, resulting in neither goal being met. It evokes the image of someone trying to sit on two stools and falling between them, suggesting a lack of focus or balance. The phrase is used in decision-making, career, or creative contexts to critique half-hearted efforts, often with a regretful or cautionary tone. It reflects the cultural value of commitment and the risks of trying to please everyone or pursue conflicting aims.

The phrase has roots in medieval Europe, with a Latin proverb *inter duas sellas cadere* (‘to fall between two stools’) attributed to Cicero (1st century BCE). In English, it appeared by the 14th century, with John Gower’s *Confessio Amantis* (1390) using ‘between two stoles.’ The modern form was recorded in John Ray’s 1678 *English Proverbs*: ‘He falls between two stools.’ The idiom gained traction in the 18th century, reflecting Enlightenment debates over balance and decision-making, as seen in Samuel Johnson’s essays. Its use grew in British and American English during the 19th century, particularly in political and literary contexts, with Charles Dickens’ *Our Mutual Friend* (1865) employing it. The phrase’s vivid imagery and universal relevance ensured its spread.