How many times on purpose?

Counting all my playthroughs in the game, probably over 100. If I did poorly in a section, I made sure she died before I went down in a blaze of glory. If she walked into my line of fire, I would sometimes kill her on purpose.

Sometimes, I would just kill her for the Hell of it. I hated that chick. 

Biggest disappointment so far for me:
a kind of bug(XD)in Jet Force Gemini made it possible to collect weapons etc.with the dog instead of the male character.So i was completely unable to beat the last boss. :(

Worst gaming frustration: getting one Great on a perfect run in DDR:

Special mention also for whenever an enemy does a critical hit in Fire Emblem and kills one of your characters at 1 or 2%. (Not so bad in FE10, with Battle Saves... but the other games don't have them!)

Also happy to see some Goldeneye 007 love in this thread.  Although for me, the hardest two time challenges to complete were Train and Caverns (the time challenge for Control was at least on Secret Agent, not 00 Agent difficulty). Can't believe it's been almost ten years since I completed that game!

The irony of this is that all the new Fire Emblems use the 2RN system which essentially means that 1% or 2% chances of anything are actually .03% and .1% chances respectively.

Just a little insult to injury there.

I remembered something. I died on level 91 of the Pit of 100 trials in Paper Mario TYD. I screamed like a little girl. Played that shit for 2 hours and died because of the game cheapness. I had 7 full healing items and lots of FP recovering items. Unfortunately I had not enough star power for nova attack. One of the 4 enemies had a clock and I was paralyzed. The worst part was Goombela using my 2 life mushrooms.

If you really want to torture yourself with escort missions, try saving everyone in Dead Rising. They'll stand around crying, they seem to run TOWARDS hoards of zombies, they'll stay locked in struggle with a Zombie for minutes at a time screaming "Frank! Frank! Frank! Frank! Frank!" and if you try to knock the damn Zombie off the crappy collision detection will interrupt it as you just attacked them instead. You give them weapons they get all cocky and start fighting every damn zombie in the area until they get stuck in a struggle with one and you have to help them again. You try and tell them to go somewhere they seem to path find towards as many damn zombies as possible in the progress. After almost any encounter they have to do their useless after battle animation/phrase and waste more time. They constantly get stuck on walls, doors, corners. They constantly fall behind if your land speed reaches excess of five miles an hour. Some of the female ones are apparently completely incapable of functioning, and need you to hold your hand while you escort them, and the awkward turning controls for this will make it easy for you to get in between a zombie or something else, separate and have to rejoin.

Hilarious thing, wounded survivors are actually the EASIEST to escort. You have to carry or lend them a shoulder. So they’re always right with you, and the kicker, you can’t get bitten while this is happening! Zombies bite moves never connect when you’re carrying someone wounded, they’re sloppy punches sometimes do, but you just get back up and keep moving.

The achievement for saving everyone is called saint, it should have been named Special Olympics Coordinator, as no one else would be capable of corralling so many mentally deficient people into a single room.

As for game breaking glitches, when I played Earthbound as a kid, I actually fucked up where you can’t progress any farther. There’s an item called the “Tiger Eye” you need to navigate a Swamp up ahead. When I got it I gave it to Poo and moved onwards, and the second I left the dungeon Poo’s Master arrived to carry him off to learn his strongest attack. He took Poo, and by extension the Tiger Eye away. At the time I didn’t realize I would need that item to keep going, and when I got to the place you use it at (Deep Darkness) I couldn’t do anything. Poo doesn’t rejoin until a battle after you use that item, and there was no way to get another. Even with the map in the player’s guide, I couldn’t get through the swamp because of inviso walls set up when you haven’t used the eye. So I had to start over, and this is about three quarters of the way through the entire game. =/

Ugh, I loved and hated Eternal Sonata. I loved it because it was absolutely beautiful and hated because the game sucked.

I didn't get real far into the game so I can only come up with two examples of why the game was terrble: the chick with the bow and Fort Fermata.

Don't get me wrong, the chick with the bow is awesome, in fact she's too awesome. She can heal your entire party and she can take out most non-boss enemies in a single hit. It's just insane how powerful she is. I was having some fun with the game and the mild difficulty until she came along and screwed everything up. Just one party member slot easily took care of healer and attacker. It was stupid how insanely good she was at everything.

And then there was Fort Fermata (think that was the name). I can ignore the chick with the bow problems, but Fort Fermata was inexcusable. It's like the developers wanted to make a study in how many things wrong they can make in a level. You're in a big round dungeon split into 2 areas, the dungeon is a maze, you have to go in and out of little buildings to move a platform, enemies respawn every time you enter a new room, there are almost no identifiable features in the dungeon, the camera moves more than 180 degrees so you get hopelessly turned around, you can't see enemies, you can't see the exit, and the list goes on. This was seriously the worst level I've ever played in a game by far.

@RolStoppable
I think laziness is the answer,instead of a real bug.I can imagine that the programmers thought that no one would ever be able to reach the parts(Homing missiles,Health tanks)with the 'wrong' character. ,So let us save this program code.' So my male character was underpowered .At least for my capabilities back then.

The ONE thing that stops the Metroid Prime trilogy from being truly great was the save system. Why cant they just let you save anytime you want?

Ivehad nights were I've nearly had to use matchsticks to keep my eyes open looking for a save point.