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The Curse of Monkey Island Hints
How do I beat the regular pirates in sword fights?
1 of 4: The trick is finding the proper responses to insults. If you insult them and they don't know the proper response, you go forward a step. If they do know the answer, they go forward a step and get to make the next insult. The same thing happens when the other pirate is doing the insulting.
2 of 4: I recommend that you try out a new insult the first chance you get. Even try coming back immediately after the current fight and use the new insult then. (Well, upgrade your cannons at Puerto Pollo first to empty your hold, just in case you lose.) If that pirate doesn't know the proper response, the next one you fight might. Keep trying pirates until you find one that does know how to respond, since you're likely to get (and need) the response later on.
3 of 4: You might also want to throw a round or two (miss a response or give an insult you know the other pirate can answer), since that gives you a chance to learn new insults.
4 of 4: As long as you've learned the proper responses, you should be pretty safe in a fight. There's no real puzzle to fighting the normal pirates -- it's just a matter of knowing the responses.