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on the shady side of

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shad⋅y

  [shey-dee]
Use on the shady side of in a Sentence
–adjective, shad⋅i⋅er, shad⋅i⋅est.
1. abounding in shade; shaded: shady paths.
2. giving shade: a shady tree.
3. shadowy; indistinct; spectral.
4. of dubious character; rather disreputable: shady dealings.
—Idiom
5. on the shady side of, Informal. beyond (the specified age); more than: on the shady side of 40.
Origin:
1570–80; shade + -y 1

Related forms:
shad⋅i⋅ly, adverb
shad⋅i⋅ness, noun
Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2009.
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Word Origin & History

shady 
"affording shade, 1579, from shade (q.v.). Meaning "disreputable" (1862) probably is from earlier university slang sense of "of questionable merit, unreliable" (1848).
Online Etymology Dictionary, © 2001 Douglas Harper
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