Might mean (unverified): Plan fails, becomes disorganized mess.
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We found one dictionary that defines the word go pearshaped:

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  1. go pearshaped: Wiktionary

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Definitions from Wiktionary (Go pearshaped)

▸ verb:  Alternative form of go pear-shaped [(intransitive, especially UK, Commonwealth, Ireland, idiomatic) To go awry; to go wrong.]

Similar:
go pear shaped, gawm, paich, pretzelise, moosh, pouff, bollox, buwang, colour up, fiz-gig, more...

Opposite:
go smoothly, go well, succeed

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Similar:
go pear shaped, gawm, paich, pretzelise, moosh, pouff, bollox, buwang, colour up, fiz-gig, more...

Opposite:
go smoothly, go well, succeed



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