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knowing
     1. adj. Possessing knowledge or understanding; intelligent.
     2. adj. Shrewd or showing clever awareness.
           a knowing rascal
     3. adj. Suggestive of private knowledge.
     4. adj. Deliberate
     5. v. present participle of know
     6. n. The act or condition of having knowledge.
     know
          1. v. To perceive the truth or factuality of; to be certain of or that.
                I know that I’m right and you’re wrong.
                He knew something terrible was going to happen.
          2. v. To be aware of; to be cognizant of.
                Did you know Michelle and Jack were getting divorced? ― Yes, I knew.
                She knows where I live.
                I knew he was upset, but I didn't understand why.
          3. v. To be acquainted or familiar with; to have encountered.
                I know your mother, but I’ve never met your father.
          4. v. To experience.
                Their relationship knew ups and downs.
          5. v. To distinguish, to discern, particularly by contrast or comparison; to recognize the nature of.
                to know a person's face or figure
                to know right from wrong
                I wouldn't know one from the other.
          6. v. To recognize as the same (as someone or something previously encountered) after an absence or change.
          7. v. To understand or have a grasp of through experience or study.
                Let me do it. I know how it works.
                She knows how to swim.
                His mother tongue is Italian, but he also knows French and English.
                She knows chemistry better than anybody else.
                Know your enemy and know yourself.
          8. v. (transitive, archaic, Biblical) To have sexual relations with.
          9. v. (intransitive) To have knowledge; to have information, be informed.
                It is vital that he not know.
                She knew of our plan.
                He knows about 19th century politics.
          10. v. (intransitive) To be or become aware or cognizant.
                Did you know Michelle and Jack were getting divorced? ― Yes, I knew.
          11. v. (intransitive, obsolete) To be acquainted (with another person).
          12. v. To be able to play or perform (a song or other piece of music).
                Do you know "Blueberry Hill"?
          13. n. (rare) Knowledge; the state of knowing.
shrewd
     1. adj. Showing clever resourcefulness in practical matters.
     2. adj. Artful, tricky or cunning.
     3. adj. (informal) Streetwise.
     4. adj. Knowledgeable, intelligent, keen.
     5. adj. Nigh accurate.
           a shrewd guess
     6. adj. Severe, intense, hard.
           a shrewd blow, or assault
     7. adj. Sharp, snithy, piercing.
           a shrewd wind
     8. adj. (archaic) Bad, evil, threatening.
     9. adj. (obsolete) Portending, boding.
     10. adj. (archaic) Noxious, scatheful, mischievous.
     11. adj. (obsolete) Abusive, shrewish.
     12. adj. (archaic) Scolding, satirical, sharp.
astute
     1. adj. Quickly and critically discerning.
     2. adj. Shrewd or crafty.
Dictionary entries from Wiktionary