Our expert says:
This is indeed an interesting question. You are correct that a calorie is a calorie no matter where it comes from and that you would have to eat a mountain of tomatoes to ingest 800 cal (889 g in fact) compared to 35,6 g of milk chocolate, however researchers have studied the effect of what happens in the body when one obtains one's energy from carbohydrates or proteins or fats and there is a difference in the subsequent metabolism. Proteins are not easily used for energy purposes, but are rather used to repair and build body tissues so they don't tend to promote fat deposition. Carbohydrates are preferentially used as our best source of energy for physical activity so unless one overeats on them, they also don't promote fat production. Fats on the other hand are preferentially stored so they do promote fat deposition. You would probably find that the chances of putting on weight are higher with the chocolate with its high fat content, than with the masses of tomatoes you would need to eat.
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