Weight loss & husband. Is this weird?

My husband says he'll give me $1,000 if I lose weight and look like I did in high school. Mind you I'm 260lbs I have pcos & hypothyroidism & I barely have time for myself because of our kids. I've been trying for years but I get busy or unmotivated but this offer has me...depressed. He constantly says he loves me for me and knows I won't lose weight(don't blame him since been years) but if he loves me why does he constantly point out my weight and even squeeze my rolls that I feel uncomfortable about. Is he just dense and think he's being nice offering a prize?🤨