Something that's knowing is sneakily wise or perceptive. A knowing smile conveys a lot of information — it implies that you know a secret or are in on some background information. Picture Mona Lisa.

A knowing glance tells its recipient that you've got them figured out or that you're aware of something they haven't shared with many people. You can use this adjective to simply mean "having knowledge" or "intentional" too, as when someone makes a knowing purchase of stolen goods. The noun version of knowing is also simple, meaning "the state of having knowledge or being aware."

Definitions of knowing
  1. adjective
    alert and fully informed
    “a knowing collector of rare books”
    synonyms: knowledgeable
    having much knowledge or education
  2. adjective
    evidencing the possession of inside information
    synonyms: wise, wise to
    having much knowledge or education
  3. adjective
    highly educated; having extensive information or understanding
    knowing instructors”
    synonyms: knowledgeable, learned, lettered, well-educated, well-read
    possessing an education (especially having more than average knowledge)
  4. adjective
    characterized by conscious design or purpose
    “a knowing attempt to defraud”
    synonyms: intentional
    resulting from one's intentions
  5. noun
    a clear and certain mental apprehension
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    awareness, cognisance, cognizance, consciousness, knowingness
    having knowledge of
    a lack of knowledge or recognition
    the fact of being aware of information that is known to few people
    cognizance, ken
    range of what one can know or understand
    farsightedness, foresight, prevision, prospicience
    seeing ahead; knowing in advance; foreseeing
    apprehension, discernment, savvy, understanding
    the cognitive condition of someone who understands
    awareness of your own individuality
    an intuitive awareness
    a general conscious awareness
    an ability to understand the meaning or importance of something (or the knowledge acquired as a result)
    an understanding of yourself and your goals and abilities
    a slight or superficial understanding of a subject
    appreciation, grasp, hold
    understanding of the nature or meaning or quality or magnitude of something
    understanding with difficulty
    understanding the nature of an event after it has happened
    brainstorm, brainwave, insight
    the clear (and often sudden) understanding of a complex situation
    realisation, realization, recognition
    coming to understand something clearly and distinctly
    type of:
    higher cognitive process
    cognitive processes that presuppose the availability of knowledge and put it to use
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