Hi Steve, moving forward always takes little steps, you can rarely change your life over night. You made huge headway in your life just recently and I know you've done some things that you were nervous about but you did them anyway (like organising your coffee morning), that takes courage but you did them successfully and you must surely have gained some confidence from that.
Is your poor health just depression or is it just general lifestyle? Why do you feel you can't chat up women now, what changed.
The only job I can think of that would enable you to leave home and develop your social life is working in a hotel, I did that when I was your age and I had a great time, I had a live in job, 3 meals a day, worked hard, played harder and managed to save money because although it's not the best wages you have no outgoings.