Didn't bother to read anything past the OP.
My advice would be, just go for it! Women are more attracted to confidence than physical features anyway. I've had lots of overweight friends who have dated/married attractive girls, because they're great guys and they're confident in who they are. Even if you don't succeed immediately - and be willing to admit when you don't - remember that everyone fails, and failure is the only way that we grow our confidence and character. If you never learn how to fail, you will never learn how to succeed. Put yourself out there and make it happen!
My advice would be, just go for it! Women are more attracted to confidence than physical features anyway. I've had lots of overweight friends who have dated/married attractive girls, because they're great guys and they're confident in who they are. Even if you don't succeed immediately - and be willing to admit when you don't - remember that everyone fails, and failure is the only way that we grow our confidence and character. If you never learn how to fail, you will never learn how to succeed. Put yourself out there and make it happen!