I've tried the quest 2 times. On both of those times the lines playing were wrong, starting at the later lines. For example at the start of the quest, in the bar, the pirate's lines start with what's supposed to be playing after the player gets beat up ("You really fell for it-.." something like that). Then during the rest of the quest the lines just continue to be played in order but obviously still multiple lines ahead.
Basically the lines start at the wrong one which makes all the lines wrong.
When all the previous lines are over but the quest is still going it seems to start playing the lines from the start of the quest.