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Is "bless your heart" something only used by old women in the South (all I've ever heard)? Or is it ever appropriate for a man to use it without seeming unmanly? Does the term always have condescending connotations?

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Did you try onelook.com/?w=bless+your+heart&ls=a –  MετάEd Dec 3 '12 at 19:14
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I've heard if from many different people, male and female. (But I can totally hear if from a southern woman best!) :-) –  Kristina Lopez Dec 3 '12 at 19:31
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At a concert, I once heard a musician (who had moved to Nashville) jokingly say that, it took him awhile to figured out, but he eventually learned that "Bless your heart" was a way for a southern woman to say "I feel sorry for you." :^) @MετάEd: One of those two OneLook links is about a song, not the phrase, and the other says nothing about who might (or might not) say it in everyday use. –  J.R. Dec 3 '12 at 19:43
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Manliness comes from delivery. See here –  tylerharms Dec 3 '12 at 19:43

4 Answers 4

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I don't recall hearing it outside the South (although on Mark Twain's evidence it seems to have been very common once in Missouri), and I've been back to the South very little in the last 20 years; but when I was growing up it was used by men and women alike, though more by women than by men.

It can be said with a forgiving intonation (“Bless your heart, how could you be expected to know?”), which inevitably has something of pity and condescension to it, and it may be ironic; but I cannot remember hearing it used sarcastically.

Its primary use, in my youth, was as an expression of admiration or gratitude for a generous action, where a mere “Well done” or “Thank you” was felt to be insufficient. It was spoken then as three stressed, spaced syllables, with a drop of at least a major third to the last:

Well, b l e s s • y o u r • h e a r t !

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Well, Mark Twain certainly used it. See his essay Fenimore Cooper's Literary Offenses, in which you'll find this passage:

We must be a little wary when Brander Matthews tells us that Cooper's books "reveal an extraordinary fulness of invention." As a rule, I am quite willing to accept Brander Matthews's literary judgments and applaud his lucid and graceful phrasing of them; but that particular statement needs to be taken with a few tons of salt. Bless your heart, Cooper hadn't any more invention than a horse; and I don't mean a high-class horse, either; I mean a clothes-horse.

It's an older expression, to be sure, and if you hear it today it's probably from a genteel old lady or gentleman — or being used sarcastically by someone else.

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Today's ancient expression from genteel elders is sometimes tomorrow's latest and greatest waykool phrase. –  Drew Sep 13 at 16:46

"Bless your heart" often is a very caring, sincere way of showing appreciation for someone's dedication, or respect for their efforts. It is very often used in a sweet, caring and somewhat maternal manner.

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I was once told that the related bless his heart or bless her heart is used as a softener when saying something negative about someone. As in "Leonard, bless his heart, has less sense than that hound of his."

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