Tricky Friendships

At what point during a realationship can you be honest with yourself that a realationship/friendship is causing more harm than good. This is a multi-faceted question. Partly because I suffer from the lost puppy dog syndrome. If I see someone who needs my help and I truely believe I can be a positive - er - personality in their life I will do my darndest to do so.
However, after the trust has been established between the said people how do you address your initial goal of helping the said person. Let's say for example one's "friend" has some social issues that you have tried to assist her with. When dealing with tender hearted situations, it's not always what you say, but how you say it. Although I am not always the most tactful person, I do try to tailor my conversations to ensure I don't harm any one's ego (although at times the http://www.sopranos.com ruff way of dealing with people appears). At what point do you let go of the friendship? I have tried for 6 months - am I giving up to soon? Perhaps I expect to much from people - and I see what she could be and want the best for her. Am I being to critical? Regardless, I am exhausted.


The truth is the world Is critical. The world Is tough - in business, in love, in friendship - you name it, it's there. Occasionally I make fun of people I don't even know (but who doesn't?)