"why oh why"? what does this mean?

Its called a figure of speach ^_^ its just like why some people type =] and :] and I type ^_^ its because I found a smiley that I like much better than the others. Certain figures of speech are just something thats fun for them to say. Its a more personalized form of speech.

Well i guess is it just your friend expressions. People have different ways to expressed there feelings over a certain question they want an answer. Such as im super duper happy lol things that are actually weird and unusual but they use those words to expressed there emotions. As to what level does your friend really need to know the answer to his question.