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I plan my cheat days around social occasions. Usually once a week... occasionally twice a week. But, I hardly ever go beyond 2,000 calories on these cheat days. I just eat food I don't normally eat... like desert, or bread, pizza, etc.
This is pretty much what I do. It's difficult to go for more than a week without "cheating," since SO much of my social life involves going out to dinner. I aim for one "cheat meal" a week, but I'll often have two or three. Even on those days, though, I rarely go over 1800 calories.