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I understand that it means to acquire a new skill, but what does it refer to? It makes me cringe every time I read it!

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OP is mistaken about the exact meaning of the expression. It's not about acquiring "new" skills, but about how you got started on the skills you already have. Here's a definition from dictionary.com

cut one's teeth on: to do at the beginning of one's education, career, etc., or in one's youth: The hunter boasted of having cut his teeth on tigers.

It's a metaphoric reference to when a baby's teeth first appear. They grow (cut) through through the gums - often painfully, which also gives us the figurative usage teething troubles.

Once the baby has "cut its teeth", it's properly equipped for the all-important "real-world" task of chewing solid food (metaphorically, for tackling more complex problems in professional life, etc.).


As that dictionary example suggests, the expression is often used boastfully/facetiously (in reality the hunter probably started with much less challenging prey, such as grubs, mice, and rabbits).

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Exactly. And children are given semi-hard things to chew on, to alleviate the pain and help the process along. –  StoneyB May 27 '13 at 16:33
    
@ StoneyB: It's only through ELU that I've come to appreciate how often idiomatic usages are mis-heard or mis-repeated. So it's no surprise to me now to see how many instances of "cut his cloth on" should clearly have been teeth, not cloth. I guess that's how language develops over decades and centuries. –  FumbleFingers May 27 '13 at 16:41
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somehow it means that you can count on something that somebody says. Ashley says it to scarlet in gone with the wind.

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You should post the actual quote from the book if using it as an example. –  dwjohnston May 23 at 0:32
    
The question asked for the origin also - just noting that it was used in "Gone With The Wind" certainly doesn't answer where it originally comes from. –  user3306356 May 23 at 2:03
    
I'd be interested to see the usage in question, which seems very unusual. –  Joe McMahon May 23 at 2:43
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@Joe: As it happens, I have the subtitles to Gone With The Wind to hand, so I can report the relevant exchange. Ashley: "Isn't it enough that you gathered every other man's heart today?". Scarlett: *"You've always had mine. You cut your teeth on it". Julie has simply misunderstood the meaning (her interpretation would make sense if you didn't know the idiom - it's just not correct). –  FumbleFingers May 24 at 19:53
    
Yep, agreed - it's the same "from early on" meaning. Thanks! –  Joe McMahon May 28 at 0:34
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