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Every day, second thing in the morning (first thing is using the bathroom). The metric that matters more to me than the daily weight, though, is a 5-day running average.
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Black coffee has almost no calories. It's any added milk, cream, sugar, syrup, or other stuff along those lines that will give you problems. Personally I drink about 3 cups a day myself with 1/2 cup of skim milk divided among them.