Usually means: With playful, knowing, subtle humor.
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We found 12 dictionaries that define the word Winkingly:

General (12 matching dictionaries)
  1. winkingly: Merriam-Webster
  2. winkingly: Collins English Dictionary
  3. winkingly: Vocabulary.com
  4. winkingly: Wordnik
  5. winkingly: Wiktionary
  6. Winkingly, winkingly: Dictionary.com
  7. Winkingly: Online Plain Text English Dictionary
  8. winkingly: Webster's Revised Unabridged, 1913 Edition
  9. Winkingly: AllWords.com Multi-Lingual Dictionary
  10. winkingly: Webster's 1828 Dictionary
  11. winkingly: FreeDictionary.org
  12. Winkingly: TheFreeDictionary.com

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Definitions from Wiktionary (winkingly)

▸ adverb:  In a winking way; with a wink.

Similar:
twinklingly, smirkingly, waggishly, hintingly, wistfully, gigglingly, squintily, flirtingly, coyishly, smilingly, more...

Opposite:
seriously, solemnly, earnestly

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Similar:
twinklingly, smirkingly, waggishly, hintingly, wistfully, gigglingly, squintily, flirtingly, coyishly, smilingly, more...

Opposite:
seriously, solemnly, earnestly



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