He REALLY likes you but isn't really fond of your body. He also thinks that when you lose weight, you will look so much better. I had a guy telling me that a while back. I was not obese, rather than just overweight. Maybe it's his way of encouraging you and motivating you to lose weight by keeping track of how much you weigh.
If it really bothers you, you may tell him in a polite way that you are on the right track taking care of your health and you don't like the constant tracking of your weight. That you appreciate but if he'd rather stop it because it makes you feel like your weight is bothering him.
I'm sure he will stop it if you want.
He may be insecure if you weigh more than him I'm guessing.
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