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  1. It's correct to use "subject + should have + past participle" to events that didn't happen?

Example: He should have gone to work yesterday.

  1. I can use this with "It"?

Example: It should have been a good friendship, but I fell in love.

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1st sentence sounds right

He missed a great party. He should have gone to work yesterday.

But 2nd one doesn't.

It could have been a great friendship but I fell in love.

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