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The comparison is more or less literal when the term is applied to people, where it means narrow at the shoulders and wide at the hips, a use that goes back to at least 1815, and one that can have either positive connotations (as in Venus figurines) or negative, depending upon the context.
In the 20th century, another, more abstract use of the term evolved. When said of someone's voice, "pear-shaped" means rich and sonorous. The Oxford English Dictionary (OED) dates this use to 1925.
The third meaning is mostly limited to the United Kingdom, Ireland and Australasia. It describes a situation that went awry, perhaps horribly wrong. A failed bank robbery, for example, could be said to have "gone pear-shaped". The origin for this use of the term is in dispute. The OED cites its origin as within the Royal Air Force; as of 2003 the earliest citation there is a quote in the 1983 book Air War South Atlantic. Others date it to the RAF in the 1940s, from pilots attempting to perform aerial manoeuvres such as loops. These are difficult to form perfectly, and are usually noticeably distorted—i.e., pear-shaped.
The pear-shaped fruit of the cashew
Pear-shaped jar from the Greek island Milos (formerly known as Melos)
Inflated party balloons
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