Should've, Shouldn't've: Fluent Speech for Modal Verbs
Speech Modification SMART American Accent Training - A podcast by Speech Modification

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In this listen and repeat shadowing practice, we use common phrases with should have (should've), would have (would've) and could have (could've), as well as the negatives shouldn't have (shouldn't've), couldn't have (couldn't've) and wouldn't have (wouldn't've). Practice integrating these contractions into fluent speech in short phrases.