Unexpectedly gone wrong or gone awry.
"Since the plane times changed my whole holiday plans have gone pear-shaped..."
by Asynca June 29, 2004
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UK slang (London)

To go wrong, to be victims of Murphy's Law. Often heard for the lips of actors in Brit crime flicks and cop shows Origin obscure.
"Bloody Hell it's the sweeny, it's all gone pear shaped"
by black flag June 26, 2004
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A Pear Shaped Diamond is either a situation gone bad or a person who has clear emotion issues normally including a alcohol dependency.
OMG! I bumped into my ex last night. It all went a bit pear shaped diamond.

OR

I bumped in to Bradley and Ashley last night. They were getting kicked out of the bar again. They are such pear shaped diamonds.
by Bashley_Uk November 16, 2009
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When the majority of things appear to be negative. Like the shape of a pear, the majority is at the bottom (bad) and little is at the top (good).
I lost my job, my girlfriend dumped me and I just got evicted. Life has just gone pear-shaped.
by sublimal June 28, 2004
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British slang term, used to describe when a situation has gone bad....I've no idea where it originates, but that's how it's used.
Since the new manager took over, things at work have gone all pear-shaped and I'm afraid I may be out of a job soon.
by Kucitizen June 27, 2004
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originates from: when a woman gets older, her breasts shrivel up and arse blooms out, giving her a figure shaped like a pear

means: its all gone wrong

see also: tits up
by itcreaks June 28, 2004
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if something has gone wrong, it has gone pear shaped
shit man. I was doing so well then it all went pear-shaped
by Paul Burton June 30, 2004
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