Stamford, I also think you should believe more in yourself but it sounds like you are stuck and in need of some counseling. Whether you choose a therapist or a coach, you can benefit from setting some short term measurable and attainable goals to get on the right track and to prove to yourself that you CAN accomplish what you set your mind to. With the right support system and the right encouragement you can learn how to get past the obstacles in your way. You might even learn what those obstacles are.
I think you would benefit more from therapy than from dating. You might not fair well right now if you get rejected because you might not understand why and might take it too personally. It would be more beneficial at this time to work on yourself and get past some of the issues that are holding you back so you can go out on the dating scene with more confidence in yourself and what you have to offer another person. And please remember getting to the Chupah is not a race. Everyone at the right time with the right person. Hatzlocha.