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I have a question.

How do you know when its time to stop trying to help someone?
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When it's causing you harm. I wouldn't measure how I am helping them unless maybe I felt I was enabling them? Even then, if it was not harming me I'd be there, as I know people don't know how to help themselves from what they battle and people give up quick. I feel being there is more and giving of more meaning than not being there, as long as you can handle what struggles it creates in you.