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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

Derived Forms

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.

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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.

At first blush, his lifetime Wins Above Replacement of 0.3 would indicate that he’s little better than the fictional minor league “replacement player” to which MLB players are compared in calculating the statistic.

From Los Angeles Times • Jun. 3, 2026

It matters because of what it signals to every other newsroom watching — every executive calculating the cost of compliance versus resistance, every journalist wondering whether their employer will protect them.

From Salon • May 13, 2026

Musk's lawyers seized on the entries to portray Brockman as a calculating opportunist.

From Barron's • May 11, 2026

This underscores the importance of a true out-of-sample test when calculating AI’s track record.

From MarketWatch • May 8, 2026

“When my darling Puss Moth’s mended I’ll give you a ride,” she offered Maddie; and Maddie, who is nothing if not calculating, asked if she could see the plane.

From "Code Name Verity" by Elizabeth Wein

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