Might mean (unverified): Older women dating younger men.
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We found 2 dictionaries that define the word cougaring:

General (1 matching dictionary)
  1. cougaring: Wiktionary

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

(Note: See cougar as well.)

Definitions from Wiktionary (cougaring)

noun:  (Canada, US, slang) The seeking of casual, often sexual, companionship of younger males by an older woman.
noun:  (roller derby) The act of deliberately picking up a minor penalty in order to visit the penalty box at a convenient time.

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