Usually means: Doubting one's initial decision, choice.
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We found 8 dictionaries that define the word second-guessing:

General (7 matching dictionaries)
  1. second-guessing: Merriam-Webster
  2. second-guessing, second-guessing: Collins English Dictionary
  3. second-guessing: Vocabulary.com
  4. Second-Guessing, Second-guessing, second-guessing: Wordnik
  5. second-guessing: Wiktionary
  6. second-guessing: Dictionary.com
  7. second-guessing: TheFreeDictionary.com

Miscellaneous (1 matching dictionary)
  1. second-guessing: Idioms

(Note: See second-guess as well.)

Definitions from Wiktionary (second-guess)

verb:  (idiomatic) To vet or evaluate; to criticize or correct, often by hindsight, by presuming to have a better idea, method, etc.
verb:  To anticipate or predict someone's actions or thoughts by guesswork.
▸ Also see second-guess





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