I usually have a general idea of what I'm getting into so I am rarely disappointed with games. When I was a kid though I made a lot of dumb mistakes...
Donkey Kong (Colecovision)
Didn't realize that there were any game systems other than Atari, and couldn't understand why the game wouldn't fit into my Atari 2600. The screenshots on the back looked so good
A lot of money to spend back then on something I could not even play.
Jaws (NES)
My mom got me and my nephew (long story short, my sister is much older than me and so her son ended up being around my age) some games for Christmas, and since she bought them blind she gave me first pick. The games were Legend of Zelda and Jaws. The cover for Zelda looked lame, so I went with the giant shark. What an awful Christmas that was. Still played the hell out of Jaws (out of desperation).
Ultima VI (C64)
One of the first games I ever bought with my own money as a kid, after enjoying the NES Ultima games and Ultima III on a friend's Atari ST.
The C64 port is an amazing effort, and I applaud the people who managed to get it done, but that game is basically unplayable on that system. You had to swap disks every time you entered and exited conversation, and with the C64 disk drive it was painful.
I spent a lot of money on this game, and the fact that I was stuck with it for the next 3 months or whatever really stung. I put up with it as much as possible and actually played it quite a bit, but I never really enjoyed it.
~From this point on, I really should have known better~
Final Fantasy XIII (PS3)
By this time I had lost interest in Japanese RPGs, and I knew the Final Fantasy series was just getting more and more heinous as time went on. The more room Japanese developers had to express themselves, the more awkward their pop culture proved to be to anyone not enamored with their cartoons. But I wanted something other than Demons Souls and the odd Muso game to play on my PS3, and man did those graphics in the previews look great.
Well, this game is irredeemable garbage. Environments are corridors, the battles play themselves (to a degree even greater than that of other Japanese RPGs), there is nothing to DO other than run down corridors and fight, the character designs are laughable, and the story is, like most modern Japanese pop culture, melodramatic to the point of unintentional comedy. Quite honestly the worst game I have ever played, and I have played some absolute garbage.
Dragon Age: Inquisition (PC)
I legitimately enjoyed Dragon Age, but Dragon Age II was awful after the first 2 hours (and not even that good until then). I simply cannot get into this game at all. I've tried 3-4 times and I just immediately lose interest.
But I actually kinda liked it. What pissed me off way more was Oblivion.
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