Now that we have the inner aspects of your life covered. Let's focus on the outer. Do you exercise at all? If not, I would recommend getting on some type of exercise program to get you into shape. You'll look better, feel better, be stronger, and all of these things will add to more confidence for you. Let me know what part of the world you are in as maybe I can recommend something.
Also, when you exercise your body starts to pump endorphins into your brain which gives you that "high" or good feeling experienced while exercising or having sex. You'll literally start to feel better through exercise.
Are you involved with any clubs at all? I have regular groups I am a part of that meet weekly and for me I've formed great friendships through that. I would recommend getting involved with some groups that you like. Aside from learning new stuff, you'll make great friends and it will also have your energy going outward into something constructive.
As for your speaking skills, I would seriously recommend that you sign up with Toastmasters
Toastmasters International - Home I think what they do fits right in line with what you would like to become.
As for going out and having fun, I would recommend you read "The Game" by Neil Strauss. It is a story of Neil, a guy who was a nerd, who became one of the top pick-up artists in the US. You might find it inspirational.