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I remember I was playing FFVIII and I had Death junctioned to Irvine's attacks. The party was then ambushed by a Malboro that confused and berserked the party. I could only watch helplessly as Irvine headshot his two partners and proceeded to commit suicide.
Needless to say the next time I fought a Malboro, I came better prepared.
I've got one. The embarrassing part is more on my personal screw-up rather than something dumb a party member did, or trying to fight something while underleveled. No, this is worse. It was my third play-through of FF III (fan translated nes version) on an emulator. Of course I was using save-states to get through the last area, and no one who has played that game could possibly blame me. It's a very, very long dungeon with no place to save. Well, I make it through and I'm fighting the boss. He kills me. I go to load my last save state and, as you probably guessed by now, I accidentally hit save instead of load. No matter how many times I frantically hit load, all I see are two dead ninjas and two dead... what were those things? Shamans? Whatever they were, they were friggin' dead. I knew at that moment that it would be a long, long time before I played FFIII again. It has been years and I still have yet to. Shame too, that's a good game =( Come to think of it, I'll give it another shot soon.
Oh, wait, I've got a better one. On my first playthrough of FFVI I couldn't beat Wrexsoul. You know, the guy that one of the strategy guides calls the easiest boss in the game. I actually had to start a new playthrough because I couldn't get out of Doma castle without beating him, and I couldn't beat him because none of my party knew X-Zone and the magicite was on the airship with someone else. Yes, the easiest boss in the game owned me so bad that somewhere, in an alternate reality of the FFVI you know, Kefka was never defeated because the heroes are trapped with Wrexsoul. The easiest boss in the game.
cloud, slash all materia got confused in i think the battle with the submarine loading arm.
Wiped out himself, Yuffie and Vincent in one swoop.
next attempt, Cloud dies, transform Vincent, arm picks up Yuffie. No conntrol and that dumb vamp messed it up big time.