I have found that eating less, even of "healthy" foods, is better for me, but as a hypoglycemic person a lot of small meals were recommended. Once I started eating more fat, a bit more protein, and cutting processed carbs out entirely...I found I was able to tolerate 3 meals a day, and I lost weight. I do think there is a calorie connection, but it's indirect. High-calorie foods are often fat/sugar bombs and it's the sugar, specifically, that is destability to blood sugar (but high sugar foods tend to also be higher in calories). For this reason, I avoid overeating and my triggers to overeat are: sugar; fat/sugar combos; eating out; eating a too large meal. I do think it's possible to eat some carbs as long as they are natural, fibrous, and eaten with fat.