I guess it depends on the food in question and your meter. I'd hope that when I lose my weight that some things like a small jacket potato or a spoonful or two of brown rice might be an occasional meal accompaniment , say once a week or fortnightly depending on blood sugars. The likes of cakes, biscuits etc, I'd say birthday or Christmas, same with a bag of crisps, maybe an ice cream once on holiday. So many things are just empty calories and I'd hate to go back to mindlessly consuming food as that is what got me here before.
I am reminded of my old next door neighbour, a very large immobile diabetic lady who had cakes on a Saturday because it was Saturday, and fish and chips on a Tuesday because she was allowed an occasional treat - it worked out that she had something every day !