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This works best when you can see visible progress from one try to the next. Dwarf Fortress is Fun because every loss is different, and you got farther/learned new things every time.

Fighting 13-year-olds in Call of Duty or League of Legends is less fun (provided you don't play much like me), because often you'll drop dead for reasons you can't divine, or anything you try loses the game with no feedback on what worked and what didn't.

(Full disclosure, I'm one of the people who doesn't take losing well.)

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