Usually means: Regret that specific day deeply.
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We found 3 dictionaries that define the word rue the day:

General (2 matching dictionaries)
  1. rue the day: Cambridge Advanced Learner's Dictionary
  2. rue the day: Wiktionary

Slang (1 matching dictionary)
  1. Rue the Day: Urban Dictionary

Definitions from Wiktionary (rue the day)

verb:  (idiomatic) To seriously regret one's actions.

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