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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.

The scheme started after the EU's Common Agricultural Policy began calculating subsidies based on land instead of livestock in 2014.

From Barron's • Apr. 3, 2026

This may have been because he was a foreigner, or a calculating businessman, but Ms. Goldring makes the case that it was Holbein’s irreplaceable artistic prowess that kept him in the king’s good graces.

From The Wall Street Journal • Mar. 27, 2026

While high-dimensional vectors can be compressed through vector quantization, that technique comes with its own memory issues as it requires calculating and storing additional data, “partially defeating the purpose of vector quantization,” Google said.

From MarketWatch • Mar. 25, 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

Maddie’s calculating smile took on a slightly evil cast.

From "Book Scavenger" by Jennifer Chambliss Bertman