Arkham Horror. I've played this game several times, and it never goes well. I want to like it a great deal, which is partly due to the setting, and partly due to it being a co-op game. Whilst I enjoy trying to beat my fellow gamers, sometimes working together to beat a game is fun.
I picked Jenny, who is the character I usually go for. I prefer playing women and I like to think of her a bit like an American, and female, Lord Peter Whimsey a dilettante detective. And smart. she starts with a skill and a spell and money isn't a problem for her.
The problem that I find every time is that the game is very complex, and is difficult to grasp for non or newer gamers. Heck, it's difficult to grasp for more experienced ones. So difficult that if you google, you can find that people have made game play flowcharts to help keep you on track. My friend had traded a game for a lot of AH expansions and they came with a handy laminated flowchart and cheat sheet instructions.
It's never a good sign when you need to draw a flowchart. It's also a game that's played best with fewer players. I think we had 7 players and it just seemed interminable. Each round was drawn out that by the time it came around to you, it was hard to remember which phase you were in.
Now that my friend has the expansions he's determined to learn and really enjoy the game, but next time i think we would play it with 4 players max, to speed up.
Oh, and for the record, we lost!