Desrtopa comments on Harry Potter and the Methods of Rationality discussion thread, part 15, chapter 84 - Less Wrong Discussion
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I wouldn't. Sign me up for unworthy adversaries all the way.
This violates fun theory if the adversaries are really unworthy.
I would do other things for fun than risk losing.
In my understanding of fun theory, you have worthy adversaries, but low consequences in case of failure. Like a video game, where if you lose, you lose a few hours of gaming at worse. Not that if you lose, you end up in Azkaban feeding the Dementors.
At least for myself, I like hard games, not easy ones, but I like it when defeat isn't too severe; I do sometimes play games in "iron will" mode (no saving, if you lose, restart all from the beginning), but not often, it's really the upper limit to what I accept when losing.