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Pear-shaped (noun) . . . The third meaning is mostly limited to the United Kingdom. It is used to describe a situation that went awry, perhaps horribly wrong. A failed bank robbery, for example, could be said to have ‘gone pear-shaped’. The phrase seems to visualise the original plan as a perfect circle, but for some reason, this became distorted in the execution. Hence the outcome was more pear-shaped. The origin for this use of the term is in dispute . . .. (Source: http://www.answers.com/topic/pear-shaped)
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Danny Dorling (2006) studied this question.
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