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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

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.

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

Meta said Ofcom's methods for calculating fees and penalties were "disproportionate", while Ofcom said it would "robustly defend" its position.

From BBC • May 7, 2026

He said Ford didn’t disregard unexpected costs such as tariffs when calculating bonuses.

From The Wall Street Journal • Apr. 22, 2026

“We’ll actually do some calculating to get a reasonable approximation.”

From "Because of Mr. Terupt" by Rob Buyea

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