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I couldn't get anywhere in Advanced Wars for the DS - it seemed like it was designed for prodigies.
Some sort of Space Shuttle simulator game on my Atari ST, that took realism to a whole new height (you'd literally have to sit and wait for the space shuttle to be moved to the launch pad with no way to skip it, and it would only let you speed it up by so much). Could never land the bloody thing, for some reason I always blew up on re-entry into the atmosphere...
I couldnt work out BOTF cause i lost the manual.
Supreme Commander maybe... too much for my little brain to comprehend in the hour or so I played it. I am sure I could have learned it though, if I had the desire to (which I did not, as I am not a big RTS guy).

In my normal genres (FPS, RPG, TBS, Adventure) I don't think there has ever been one that I felt too stupid for. Myst and Riven maybe, though I think that was more about not wanting to bust out a pen and paper.
I find realistic simulators (like those from submarines and such) to be not only boring, but too complex for my mind to grasp some of the concepts, specially since I'm waiting to have fun, not to learn something new.
That's the way you feel when starting any Paradox game.
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stonebro: That's the way you feel when starting any Paradox game.
This is so true. I remember when I first fired up Europa Universalis 3 complete...

I was like "O.o"
I bought Freespace on GoG just to see what game like that are like and the controls for keyboard were bad but it kinda made me feel stupid. I know they're controllers specifially for game like this but I don't really want to buy an expensive, used and worn controller on one game.
Pizza Tycoon, no matter how i looked at the graphs, advertised, and how awesome my pizzas and staff were, nobody came to my restaurant, and my revenue was always low, and i kept losing after a week or two. Now i feel economically dumb, and try not to get involved in money related things.
Europa Universalis III. Started game, confused, quit game, uninstalled.
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stonebro: That's the way you feel when starting any Paradox game.
So true. I tried a demo of a couple of their games. Couldn't understand a thing even during the tutorials =/
Chessmaster. Got my ass handed to me on a silver platter.
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deshadow52: I bought Freespace on GoG just to see what game like that are like and the controls for keyboard were bad but it kinda made me feel stupid. I know they're controllers specifially for game like this but I don't really want to buy an expensive, used and worn controller on one game.
Try Mouse + Keyboard combo. It should be playable / enjoyable.
Maybe Dwarf Fortress.
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deshadow52: I bought Freespace on GoG just to see what game like that are like and the controls for keyboard were bad but it kinda made me feel stupid. I know they're controllers specifially for game like this but I don't really want to buy an expensive, used and worn controller on one game.
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Sulibor: Try Mouse + Keyboard combo. It should be playable / enjoyable.
yeah someday I will try that.