I have a shyness problem. I have read a lot of self help stuff that seems to say that by NOT trying to get out and talk to people I don’t know I am only making my fears and insecurities stronger. I made a new years resolution to talk to a stranger everyday (something I read on a blog as an idea to overcome shyness). Unfortunately, after about a month of really doing this I feel worse than ever. At best people react neutrally when I try to initiate a conversation and more likely they pretty much reject me totally. So after a month of trying to overcome my fears I have come to realize that my fears were actually very justified. So what now?
Much ink has been spilled on the topic of shyness and social phobia, which it sounds like you may be struggling with (although lots more information is needed before a diagnosis could be made).
Whether or not your particular problem is severe enough to warrant a diagnosis, I believe you could benefit a lot from seeing a counselor to help you deal with this. A trained professional could help guide you through the steps and work with your individual needs and strengths.
Self-help books are great, but they can't replace a human being who can give you the personal attention you need. Your problem is not insurmountable; you just need the right kind of help.
Good luck, and feel free to contact me if I can be of further help.