Used and loved by millions
Since I tried Ludwig back in 2017, I have been constantly using it in both editing and translation. Ever since, I suggest it to my translators at ProSciEditing.

Justyna Jupowicz-Kozak
CEO of Professional Science Editing for Scientists @ prosciediting.com
calculating smile
Grammar usage guide and real-world examplesUSAGE SUMMARY
The phrase "calculating smile" is correct and usable in written English.
It can be used to describe a smile that suggests someone is thinking strategically or assessing a situation, often with a hint of cunning or cleverness. Example: "She greeted him with a calculating smile, as if she were already planning her next move in the negotiation."
✓ Grammatically correct
News & Media
Science
Academia
Alternative expressions(4)
Table of contents
Usage summary
Human-verified examples
Expert writing tips
Linguistic context
Ludwig's wrap-up
Alternative expressions
FAQs
Human-verified similar examples from authoritative sources
Similar Expressions
60 human-written examples
"She is nervous," Joseph Heller writes, as the main character Bob Slocum, "spiteful, embittered and vindictive" behind her "thin-lipped smile of calculating villainy... she must continue to agitate, like some dark and moody burrowing creature with a drive to undermine and destroy".
News & Media
Behind her blue eyes and sweet smile lies the calculating heart of a girl determined to stay alive no matter the cost..
Academia
"Signing Jamie was a calculated risk," Kear smiled.
News & Media
Some degree of rudeness can be permitted to such figures as Her Majesty's judges, stipendiary magistrates or members of the crown prosecution service, although such attacks should be, according to Mr Rumpole, free of racist abuse, elegantly phrased and calculated to raise a smile, or even a suppressed giggle, from the members of the jury.
News & Media
New Excel formulas are also available - for calculating molecular descriptors, molecular weight or molecular formula and for determining whether one Smiles string is a substructure of, or is similar to, another Smiles string (within a defined threshold).
Science
Avoiding conflict and flashing a friendly smile does not excuse one from gossiping viscously, insulting others or being manipulative and calculating in secret.
News & Media
He smiled at Kiera from his seat on the curb, head still dizzy from calculating the profit he'd reap after marking up these false timepieces.
News & Media
The Chi descriptor is calculated by matching all Smiles Arbitrary Target Specification (SMARTS) patterns in CDK.
Science
From the characterization results, as shown in Fig. 1g, h, the mean diameters of Ag@SiO2 nanostructures were 26 ± 2.3, 32 ± 3.6, 39 ± 2, 44.1 ± 3.3, 58.2 ± 2.5, and 62.2 ± 3.2 nm, calculated with the assistance of Smile View software, and the interparticle distance decreased from 19 to 0 nm.
Science
Based on the books' detailed descriptions of provenances, nosy readers can calculate what Mr. Schorsch and Ms. Smiles have spent at auction on Dr. Katcher's behalf.
News & Media
In the SMILE, an index of weighting (IOW, 20 100), an index of satisfaction (IOS, 0 100), and a total SMILE index (IOWS, 0 100) are calculated from the areas mentioned by the participants as providing MIL.
Expert writing Tips
Best practice
Use "calculating smile" to describe a smile that is not genuine or spontaneous, but rather carefully crafted to achieve a specific effect or to conceal true intentions.
Common error
Do not use "calculating smile" indiscriminately; reserve it for situations where the smile genuinely reflects strategic or manipulative intent, as overuse can weaken its impact.
Source & Trust
82%
Authority and reliability
3.8/5
Expert rating
Real-world application tested
Linguistic Context
The phrase "calculating smile" functions as a descriptive element, modifying the noun "smile" with the adjective "calculating". Ludwig AI examples showcase its usage to depict a smile that is not spontaneous but rather intentional and strategic.
Frequent in
News & Media
33%
Science
33%
Academia
33%
Less common in
Formal & Business
0%
Encyclopedias
0%
Wiki
0%
Ludwig's WRAP-UP
The phrase "calculating smile" describes a smile that is strategic and intentional, rather than genuine. Ludwig AI confirms its grammatical correctness and provides examples of its use in literature, news, and media. It's often used to imply that the person smiling has ulterior motives or is carefully considering their next move. While not extremely common, its presence in reputable sources suggests it is a valid and descriptive phrase. Consider using alternatives like "shrewd smile" or "cunning smile" depending on the specific shade of meaning you want to convey. Be mindful to not overuse the term, reserving it for instances where strategic or manipulative intent is clear.
More alternative expressions(6)
Phrases that express similar concepts, ordered by semantic similarity:
shrewd smile
Replaces "calculating" with "shrewd", emphasizing cleverness and astuteness.
cunning smile
Substitutes "calculating" with "cunning", highlighting a deceptive or manipulative aspect.
knowing smile
Replaces "calculating" with "knowing", suggesting awareness of something others don't.
scheming smile
Emphasizes the planning or plotting aspect behind the smile.
strategic smile
Highlights the intentional and planned nature of the smile.
deliberate smile
Suggests the smile is carefully considered and not spontaneous.
purposeful smile
Implies the smile is used to achieve a specific goal.
measured smile
Indicates a controlled and thoughtful smile.
artful smile
Suggests the smile is skillfully crafted to create a certain impression.
designing smile
Implies a manipulative intention behind the smile.
FAQs
What does "calculating smile" mean?
A "calculating smile" suggests that the person is smiling while also thinking strategically, often with a hint of shrewdness or planning. It implies the smile isn't entirely genuine.
How can I use "calculating smile" in a sentence?
You might say, "She gave him a calculating smile, as if she already knew the outcome of their negotiation."
What are some alternatives to "calculating smile"?
You can use alternatives like "shrewd smile", "cunning smile", or "knowing smile" depending on the specific nuance you want to convey.
Is "calculating smile" a positive or negative description?
It's generally a negative description, as it implies a lack of sincerity and suggests the person is using their smile for strategic or manipulative purposes. But depending on the context, it can be neutral, too.
Editing plus AI, all in one place.
Stop switching between tools. Your AI writing partner for everything—polishing proposals, crafting emails, finding the right tone.
Table of contents
Usage summary
Human-verified examples
Expert writing tips
Linguistic context
Ludwig's wrap-up
Alternative expressions
FAQs
Source & Trust
82%
Authority and reliability
3.8/5
Expert rating
Real-world application tested