Usually means: Enjoy benefits of opposing choices.
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We found 8 dictionaries that define the word have it both ways:

General (6 matching dictionaries)
  1. have it both ways: Oxford Learner's Dictionaries
  2. have it both ways: Collins English Dictionary
  3. have it both ways: Cambridge Advanced Learner's Dictionary
  4. have it both ways: Wiktionary

Miscellaneous (1 matching dictionary)
  1. have it both ways: Idioms

Slang (1 matching dictionary)
  1. Have it both ways: Urban Dictionary

Definitions from Wiktionary (have it both ways)

verb:  (idiomatic) Synonym of have one's cake and eat it too

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