Learn what "i shouldn't have left you last night" means, when people say it, and how to use it naturally in English.

It means the speaker feels sorry about leaving and thinks it was a mistake.
From Collateral Hearts, Episode 58
Someone regrets leaving another person the night before.
Use this to apologize for leaving someone or to admit regret after a fight or breakup tension. It sounds personal and emotional, not formal.
Scenes unlock real expressions as you watch
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