Monopoly, the board game. My family has so many versions of it. Farmopoly, Birdopoly, oh and don't forget the credit card one! Each time one of them cranks one out, I internally die. For the life of me, I cannot win a single game because my brother somehow always buys the property I always land on. I forfeit the moment that happens because I can never pick myself up from the loss.
If we're talking video games on the other hand...
I'll admit to say I gave up with Majora's Mask after the second dungeon. I got a bit lost of what to do next and never picked it up again. The three-day limit always made me anxious, too. This is one of the only games that made me extremely anxious whenever the next day would come, and I would end up resetting the clock and trying to do a dungeon or side-quest again.
The original Kingdom Hearts is a chore. I started playing it during the summer of this year and just stopped. It's exhausting and the slowest game I had ever played. The last world I completed was the whale? I had to look it up to make sure that it's name was Monstro. I want to get through this game, as I would like to get myself into the KH series. But I don't know how I'm supposed to when the first installment is like this!
GTA IV. Another slow and apparently long game. It's been a while since I last touched it. I have no idea where I left off, but I remember hating driving around Liberty City. And that's kind of a vital asset.