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Synonyms

calculating

American  
[kal-kyuh-ley-ting] / ˈkæl kyəˌleɪ tɪŋ /

adjective

  1. capable of or made for performing calculations, especially arithmetical calculations.

    a calculating machine.

  2. shrewd; cautious.

    a wise and calculating lawyer.

  3. selfishly scheming.

    a cold and calculating dictator.

    Synonyms:
    designing

calculating British  
/ ˈkælkjʊˌleɪtɪŋ /

adjective

  1. selfishly scheming

  2. shrewd; cautious

"Collins English Dictionary — Complete & Unabridged" 2012 Digital Edition © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012

Other Word Forms

  • calculatingly adverb
  • noncalculating adjective
  • uncalculating adjective
  • uncalculatingly adverb

Etymology

Origin of calculating

First recorded in 1800–10; calculat(e) + -ing 2

Explanation

Someone who's calculating is scheming to get exactly what they want, no matter the cost to other people. A movie's calculating villain might be determined to steal his innocent victim's money. The adjective calculating originally meant simply "doing calculations," or in other words, doing math. It quickly took on a figurative meaning that's become its main definition, used for anyone who directs their intelligence and know-how toward ruthlessly getting the best of other people. Your brother's calculating smile is a sure sign he's up to no good.

Keep Reading on Vocabulary.com

Vocabulary lists containing calculating

Example Sentences

Examples are provided to illustrate real-world usage of words in context. Any opinions expressed do not reflect the views of Dictionary.com.

And when aggregating a value-weighted portfolio of all common stocks over this 100-year time frame and calculating their performance, only 27.60% of stocks beat the market.

From MarketWatch • Apr. 14, 2026

If this was a crime of passion, it was meticulously laid out, but eventually it was exposed as a cold and calculating house of cards that came crashing down.

From BBC • Mar. 23, 2026

Predicting what may happen with the third, before calculating the second, only makes the first step seem even more frenzied.

From Barron's • Mar. 19, 2026

The solution of indexing capital gains to inflation would correct this distortion by adjusting the original purchase price for inflation before calculating taxable gains, ensuring that only genuine appreciation beyond inflation is subject to taxation.

From Los Angeles Times • Mar. 19, 2026

It eyed them in a most calculating way and once, when Nhamo teased it with a stick, it rose up with its yellow mouth open wider than she had dreamed possible.

From "A Girl Named Disaster" by Nancy Farmer