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What is "on the shady side of"

The Collaborative International Dictionary
On the shady side of

Shady \Shad"y\, a. [Compar. Shadier; superl. Shadiest.]

  1. Abounding in shade or shades; overspread with shade; causing shade.

    The shady trees cover him with their shadow.
    --Job. xl. 2

  2. And Amaryllis fills the shady groves.
    --Dryden.

    2. Sheltered from the glare of light or sultry heat.

    Cast it also that you may have rooms shady for summer and warm for winter.
    --Bacon.

  3. Of or pertaining to shade or darkness; hence, unfit to be seen or known; of questionable character; unsavory; equivocal; dubious, corrupt, or criminal; as, a shady character; -- of people or activities. [Colloq.] ``A shady business.''
    --London Sat. Rev.

    Shady characters, disreputable, criminal.
    --London Spectator.

    On the shady side of, on the thither side of; as, on the shady side of fifty; that is, more than fifty. [Colloq.]

    To keep shady, to stay in concealment; also, to be reticent. [Slang]

Wiktionary
on the shady side of

prep.phr. On the further side of.

Usage examples of "on the shady side of".

He naturally stationed himself to seaward on the shady side of the long promenade deck.

You know how they clam up on you as soon as you press them for details about word on the shady side of the street.

It was early spring, with patches of snow still holding on the shady side of the hills.

Consequently Pengelly came out on the shady side of the place where a porticoed building cast a sombre shadow on the pavement.