What is a "Wry Smile"? Meaning, Examples, Synonyms & More

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Everything you need to know about spotting & interpreting a wry smile

Co-authored by Asa Don Brown, PhD, DNCCM, FAAETS and Glenn Carreau

Last Updated: June 19, 2025 Fact Checked

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• What is a “wry smile”?
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• What does it look like?
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• What does it mean?
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• Wry Smile vs. Smirk
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• Wry Smile Synonyms

|Show more |Show less

Maybe you’ve read the phrase “wry smile” in a book or heard someone use it to describe an expression—but what is a wry smile? And what does it mean when someone smiles “wryly” when they’re talking to you? We’ve got the answers. A wry smile is one typically used to point out the humor in an unexpected or unpleasant situation. Because “wry” also meant contorted or bent, wry smiles usually look lop-sided or crooked. In this article, we’ll cover the full definition of a wry smile, with examples of how you might see it used in real life and more!

Wry Smile Meaning at a Glance

A “wry smile” is a facial expression that conveys humor or irony when something totally unexpected happens. It can also be used to hide your dismay or disappointment. Wry smiles are usually subtle and crooked; they look like a half-smile with one corner of the mouth turned up.

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Section 1 of 5:

What is a “wry smile”?

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1. 
   A “wry smile” is an expression showing humor in a bad situation. “Wry” is an adjective describing what the smile looks like—and a “wry smile” (or “wry expression”) is used to show when someone finds a negative situation or sudden change to be slightly amusing. In the same way, you can also make a “wry comment,” or have a “wry sense of humor.”

   • Pronunciation: RAI. “Wry” is also pronounced the same as the word “rye.”
   • She left work early, only to get caught in an hour-long traffic jam. In response, she just gave a wry smile and shrugged.
   • They thought he’d be upset at the last-minute bad luck, but he took it in stride with a wry smile.
   • Her wry half-smile told him that something must have gone wrong.
   • By itself, “wry” is an adjective meaning twisted or bent abnormally. Thus, “wry smile” describes the shape of the smile as well as the emotions behind it: bent, crooked, or slightly contorted to one side.
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Section 2 of 5:

What does a wry smile look like?

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1. 
   Wry smiles typically look crooked or twisted in some way. Wry smiles don’t necessarily have a specific appearance; a wry smile is more about the context in which it’s being used. Generally speaking, since “wry” means bent or twisted, wry smiles tend be subtle and asymmetrical. They may look like a small half-smile with only one corner of the mouth slightly upturned (as opposed to a full, genuine smile)..

   • Since wry smiles are usually only half-smiles, you probably won’t see any teeth. They might even look tight-lipped (if they’re focused on an ironic or negative situation).
   • When someone is smiling wryly, you might see a slight expression of contempt or bitterness on their face as well.

Section 3 of 5:

What does it mean when someone “smiles wryly”?

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1. 
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   They might be acknowledging an ironic twist or change. Irony occurs when whatever happens is the opposite of the expected outcome. So, if someone is expecting one thing to happen and instead gets thrown a curve-ball as something else happens instead, they might use a wry smile (or comment) to express how they feel about it. For example:

   • She came downstairs to find her dog ripping up the training certificate he’d earned. “I guess you didn’t learn as much as I thought,” she said with a wry smile.
   • He studied all day, but realized with a wry smile that he still blanked on the first question of the test.
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   They could be masking disappointment or dismay. A wry smile is often used when recognizing and pointing out the humor in a negative situation. To that end, it’s possible you might see someone give a wry smile when they’re also trying to cover up their disappointment, disgust, or frustration with that sense of humor. For example:

   • Not long after it started raining, he got the notification his concert was canceled. “So…are there any good movies playing?” he asked his friend wryly.
   • The doctor’s note told her she’d have to rest in bed for several days—so she couldn’t go on her planned trip. “Well, at least I’ll still get to sleep in,” she told herself with a wry smile.
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   They might actually think a situation is funny (even if it’s negative). Since wry smiles signal when someone finds their current situation amusing, they’re not always a bad sign. Sometimes, a wry smile can mean that even if a situation is unexpected or not totally ideal, they can see and appreciate the humor in it, too. For example:

   • “I love my cat so much, I don’t even care that letting her sleep on my bed makes my allergies go wild,” she said, smiling wryly.
   • He put on a floppy hat, smiling wryly. “I love warm weather but burn super easily. It’s a curse.”
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Section 4 of 5:

Wry Smile vs. Smirk

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1. 
   Wry smiles are ironic, whereas smirks convey smugness. When someone gives a wry smile, it’s because they’re pointing out the humor in an ironic situation. When someone smirks, it’s usually because they feel smug about something, or they’re trying to be condescending or arrogant. In other words, smirks tend to be either teasing or outright mean-spirited.

   • Wry smiles can also be sarcastic, self-deprecating, or subtle and half-hearted. By comparison, someone smirking is more likely to be self-satisfied (or may be mocking someone else).
   • Physically, wry smiles usually look like small half-smiles. On the other hand, smirking is a more obvious type of smile—and the person smirking may have narrowed eyes or a scrunched nose if they’re trying to be mean-spirited.

Section 5 of 5:

Synonyms for Wry Smile

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1. 
   “Wry” is a pretty specific descriptor for a smile, but there are a few other words that can be used as synonyms (or, at least, that are very similar). Since “wry” smiles are mainly associated with irony and grim humor, synonym phrases could include:

   • Ironic smile. “Ironic smile” is probably one of the closest synonyms to “wry smile,” since someone can give a “wry” smile when acknowledging irony—so, they might give an “ironic” smile in the same type of situation.
   • Crooked smile. Instead of describing an emotion or situation, you could use a synonym describing what the actual smile looks like—and since “wry” means twisted, crooked, and warped, any of those words can be synonyms.
   • Sardonic smile. “Sardonic” means grimly humorous, cynical, or scornful—which makes a sardonic smile very similar to a wry one. Just keep in mind that “sardonic” can refer to mocking another person, whereas “wry” is more about recognizing the humor in a bad situation.
   • Cynical smile. “Cynical” means distrustful, pessimistic, and generally believing people are motivated by selfishness. While it’s not the same as “wry,” a cynical person could definitely smile wryly when faced by bad situations.
   • Knowing smile. “Wry” indicates some self-awareness (because it refers to acknowledging something negative about a situation), so you could say “knowing smile” instead.
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