2nd-Q not a problem today, but when much younger it didn't help. I learned it means different things in different social settings or situations. The best thing I learned is sometimes,not all the time, when a young woman asked me if I was shy it was a signal that approaching her was OK.
3rd-Q again when more youthful and it was a friend of the same gender I punched 'em in the nose (smile)
4th-Q A) tips take a sociology class and an intro to psychology if you can. you will discover things about people in general that will empower you on the intellectual side. Look into wellness and the wellness circle. Look into the 10 different kinds of intelligence. And most importantly remember "you are a unique individual unto yourself and there is nobody else like you are" Many have similar interests, likes, dislikes etc., but you are you and that is cool.
4th-Q B) remember, these are my view and not gospel. Shyness is a positive thing in many cases. It is a cautious behavior, usually a protective mode of personality for some cause. Learn to trust your shyness as a friend. I would bet you are not shy when in a comfortable situation, eh? With experience(s) we gain knowledge and understanding becoming more comfortable in varying circumstances and various social settings. And, remember to smile and have fun, fun, fun , , ,