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The words "stoic" and "stolid" seem quite similar to me:

stoic: seeming unaffected by pleasure or pain; impassive [cite]
stolid: having or revealing little emotion or sensibility; not easily aroused or excited [cite]

When would you use one versus the other? Under what circumstances would you not use one of them?

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When describing people, stoic has a particularly heroic connotation. A stoic person really braves everything that man, nature, and God throws at him without complaint. Stolid, on the other hand, is not so: You might use it to describe someone who showcases a simple faithfulness, a "friend through thick and thin," but you might also use the word to describe someone who's plodding and utterly unadaptable to change.

Job, of the Book of Job, is stoic. Watson, of Sherlock Holmes, is stolid.

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I think that is a bit unfair on Dr. Watson. –  z7sg Ѫ Mar 22 '11 at 16:24
    
@z7sg Do you maintain that stolid has negative connotations, then? Or that he warrants more praise that stolid alone supplies? –  Phrogz Mar 22 '11 at 16:57
    
Yes to both questions. :) I imagine a stolid person to be passive and somewhat charmless. Watson often plays an emotional and moral counterweight to Holmes who has a detached and almost amoral nature. He's also quite a brave man and not afraid to take the initiative in his friend's absence, though not always successfully. –  z7sg Ѫ Mar 22 '11 at 17:17
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There is, of course a significant difference in the etymology of the two words, i.e. stolid cite, which derives from a Latin word meaning foolish or stupid, and stoic cite, which ultimately derives from the Greek for a painted porch (referring to the location where Zeno is said to have taught).

From a usage point of view, I'm of the opinion that stolid means "unfeeling" in the sense of lacking feeling all together (or lacking a particular sensibility), whereas stoic implies bearing up under the weight of one's emotions (the goal of Stoic practice being apatheia, the cultivation of a state of being unaffected by the emotions).

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The part about pleasure in your definition of stoic sounds weird to me, because it is one of the things that differentiate the two words for me: stoic is all about withstanding pain and suffering (will and strentgh), while stolid is more about minor character traits.

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