re: Creative ways to encourage or deal with a SO who hasn't aged well?

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If you're the man, learn to cook. She'll eat healthy if you're preparing the meal.

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I know how to cook. I learned to cook from my grandmother and in hunting camps. There ain't much healthy about it.

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And every time she loses a little bit of weight, praise her for it.

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I'd be careful with that. You better make sure she decides that "she is trying to lose weight", otherwise the first time you praise her for losing some, she'll pull the "so, you think I'm fat?" fight card out.