Usually means: Unclear, informal romantic or sexual relationship.
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We found 4 dictionaries that define the word situationship:

General (3 matching dictionaries)
  1. situationship: The Word Spy
  2. situationship: Wiktionary
  3. Situationship: Wikipedia, the Free Encyclopedia

Slang (1 matching dictionary)
  1. situationship: Urban Dictionary

Definitions from Wiktionary (situationship)

noun:  (neologism, informal) A romantic or sexual relationship in which the parties involved do not clearly define their relationship as such, but for example consider it "complicated" or a friends with benefits-type situation.

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