Usually means: Female school crossing patrol officer.
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We found 7 dictionaries that define the word lollipop woman:

General (7 matching dictionaries)
  1. lollipop woman: Oxford Learner's Dictionaries
  2. lollipop woman: Vocabulary.com
  3. lollipop woman: Dictionary.com
  4. lollipop woman: Rhymezone
  5. lollipop woman: FreeDictionary.org
  6. lollipop woman: Mnemonic Dictionary
  7. lollipop woman: TheFreeDictionary.com

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Definitions from WordNet (lollipop woman)

▸ noun:  a woman hired to help children cross a road safely near a school


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