Etymology
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calculating (adj.)

1710, "carrying out calculations," present-participle adjective from calculate (v.). Meaning "given to forethought and shrewdly or selfishly seeking advantage, scheming," is attested from 1802.

calculating (n.)

1710, "calculation," verbal noun from calculate (v.). Calculating-machine "mechanical computer, machine which performs mathematical calculations" is from 1830 [Babbage].

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Definitions of calculating

calculating (adj.)
acting with a specific goal;
the most calculating and selfish men in the community
Synonyms: calculative / conniving / scheming / shrewd
From wordnet.princeton.edu