Usually means: Letter ending a romantic relationship.
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We found 14 dictionaries that define the word dear john:

General (10 matching dictionaries)
  1. Dear John: Merriam-Webster
  2. Dear John: Oxford Learner's Dictionaries
  3. Dear John: American Heritage Dictionary of the English Language
  4. Dear John: Infoplease Dictionary
  5. Dear John: Dictionary.com
  6. Dear John (American TV series), Dear John (British TV series), Dear John (Eddi Reader song), Dear John (Hank Williams song), Dear John (Status Quo song), Dear John (Taylor Swift song), Dear John (U.S. TV series), Dear John (UK TV series), Dear John (US TV series), Dear John (disambiguation), Dear John (film), Dear John (novel), Dear John, Dear john: Wikipedia, the Free Encyclopedia
  7. Dear John: TheFreeDictionary.com
  8. Dear John (letter): Cambridge Advanced Learner's Dictionary
  9. Dear John: Merriam-Webster
  10. Dear John: Wiktionary

Computing (1 matching dictionary)
  1. Dear John, Dear John: Encyclopedia

Slang (3 matching dictionaries)
  1. Dear John: Green’s Dictionary of Slang
  2. Dear John: English slang and colloquialisms used in the United Kingdom
  3. DEAR JOHN: Urban Dictionary

Definitions from Wiktionary (Dear John)

noun:  (often attributive) A Dear John letter in any form or medium.

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