I know that "in bocca al lupo" means "good luck", but what's its origin and when is it used?
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Let me copy down the (not completely satisfying) relevant entry from Carlo Lapucci, Dizionario dei modi di dire della lingua italiana (Garzanti-Vallardi, 1979):
So, in a sense, you are apparently wishing for a dangerous situation, but implicitly suggesting that your friend will be successful.
I myself do not know any hunter, but «In bocca al lupo!» is used quite frequently before exams, performances, job interviews and the like, while some people (like the hunters of the above quotation) would consider a more straightforward wish to be unlucky.
Compare the above with the English “Break a leg!”
No no no no no!!!! All answers are TOTALLY wrong!! Let me explain why! The female of the wolf, when it has her puppies (her 'children'), it use to put them in her mouth to PROTECT them from external attacks.
So, when somebody says "in bocca al lupo" it means "I hope you'll receive a protection". So the correct reply is "grazie", that means "thank you (that you want to 'protect' me)! Do you understand?
"in bocca al lupo"(in the mouth of the wolf) is an expression from the novel "Cappuccetto Rosso" (Little Red Riding Hood), in fact you answer "crepi!"(die! referred to the wolf) because the girl manages to kill the wolf with the help of a huntsman instead of being eated