When I was growing up my brother and I used to spend a week each summer at our cousins' house. They had a copy of Monkey Island and each summer we would tell ourselves, "This is the year we're going to beat Monkey Island." Each year we never made it much further than the first Island. Eventually our cousins lent us the game and we beat it over the course of a few months.

Interestingly, I think about Monkey Island a lot because I often tell people (only half jokingly) that the way that I think about learning conversational skills is by using the same mechanics as the sword fighting challenge in The Three Trials. As you gain experience sword fighting, you pick up new phrases and you eventually learn the situations in which you yourself can apply those phrases appropriately to defeat the other swords[wo]men. Similarly, I've found it quite effective to watch how other people use techniques to illicit specific reactions from people. After a while of seeing the same technique applied by different people for slightly different reasons, you can start using it yourself. Eventually you have a big bucket of techniques you can use whenever!