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Dear LittleWren:
You wrote: “I’ve tried to be as supportive and encouraging .. but.. it’s becoming exhausting… makes him feel worse”-
better stop doing what has not worked for you or for him. Better stop being supportive and encouraging and instead let him be as he is, leave him be in his confusion, loss, lack of purpose. It might be just what he needs: to be left alone, to be .. allowed to be and feel what he feels, for as long as he is and feels the way he does. To not be pressured to find a purpose, to not be pressured to feel differently than he does.
When a person we care about is troubled, our first inclination is to do something. Often enough, what the person needs us to do is… nothing at all. Just be there like before.
anita