Is it a personal failing to keep having to lose weight you already lost?

Not so much.  As formerly quite large people we developed an idea of what’s a reasonable amount of food per meal and per day, and that amount is actually pretty inflated.  It’s difficult to change and will likely be a lifelong attitude adjustment process.  You may continually find yourself up from where you want to be and need to work hard to get back down to your healthy weight.

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