1

Go pear shaped (The plan isn't working / plan is going wrong)

... In all likelihood, this has nothing to do with the fruit, but rather plays off of the expectation of something being round, but instead having it be an odd shape.

Could I have your help in interpreting the phrasal verb? I looked it up in dictionaries. It has several meanings. I expect that means 'to react to or interact with, as in a drama'. I'm not sure of whether I am right though.

3

Both "play on (something)" and "play off (something)" mean to use that thing as a starting point for some variation, often humorous or interesting. Many jokes are a play on words, meaning that they manipulate some expected phrase in a clever way. An English pun:

In the winter my dog wears his coat, but in the summer he wears his coat and pants.

I could say this is a play on/off of "coat and pants", common articles of clothing. An animal's fur, collectively, is referred to as his "coat", or "coat of fur". Meanwhile "pants" as a noun means trousers, but as a verb means to breath heavily. Dogs pant when they are tired or overheated.

So in summer, an overheated dog will wear his coat (of fur) and pant (breath heavily).

There is little difference between "play on" and "play off". The nuance is mostly directional, and which you choose to say depends on context and individual preference.

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