You can't help him—he has to help himself. You can, however, recommend he make some changes, but if he doesn't pursue them and doesn't improve, it's best to remove him from your life.
My recommendation is that he googles 'No More Mr. Nice Guy pdf' and clicks the first link he finds. He needs to learn how to be a more grounded man and more stoic. There are plenty of resources online.
Only through daily, constant improvement (working out, learning skills, etc) will he build that self esteem.
IIN to think he'll be lonely and unhappy if he won't change?
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You can't help him—he has to help himself. You can, however, recommend he make some changes, but if he doesn't pursue them and doesn't improve, it's best to remove him from your life.
My recommendation is that he googles 'No More Mr. Nice Guy pdf' and clicks the first link he finds. He needs to learn how to be a more grounded man and more stoic. There are plenty of resources online.
Only through daily, constant improvement (working out, learning skills, etc) will he build that self esteem.