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Holy Kipper!
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Day 5: The most challenging game you've played.
The Elder Scrolls: Oblivion. Couldn't get out of the starting sewer area.
Really? It's not that hard, just long and confusing. And there is a difficulty setting. But I will admit, some other parts of the game (Notably the arena) have insanely difficult battles, even on normal difficulty.
But for me, I'd have to say Final fantasy X. Idk why but I always get stuck somewhere. First I got stuck on evrae, then I got stuck on Biran and Yenke, and then I kinda skipped the rest of the game due to an exploit :p