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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.

It’s a move he’s done for years, calculating what exactly he owes in taxes, and then going out of his way to make sure the government doesn’t get a penny more.

From MarketWatch • Apr. 6, 2026

What’s more, Nasdaq will multiply that percentage float by three-times, in calculating the weight of a low-float addition to the index.

From Barron's • Apr. 1, 2026

"We are calculating our steps with extreme precision and working to keep Syria away from any conflict," he said in a speech after Eid al-Fitr prayers in the capital.

From BBC • Mar. 20, 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

“I could teach you German,” I offered casually, while calculating the months this endeavor would take.

From "Not Nothing" by Gayle Forman