Eternal sonata.
part way through the game polka (my healer) got infected with eternal darkness (meaning she couldn't heal anymore). trash mobs weren't much of a problem so i kept on going, but then i got to the boss fight and it was impossible to win without a healer.
turns out (according to gamefaqs) that i was suppose to pick up an item in the previous level to cure polka. well it was too late to go back. I ended up having to grind 4 levels to so that fredrick would have a proper healing spell. the grind took about 2 hours. about 1 hour into the grind i saw an "x" on the ground and decided to pick it up, it was an optional boss fight that i of course lost, died, and lost my first hour of mob grinding. I was soo pissed i threw the game down for 2 weeks.
if it was WoW i would have thought nothing about the grind but in a consol game it just pissed me off soo much.