If you want to understand why people say the things they say, do a little social experiment. Record conversations, word for word, (yes this is a bit sneaky and perhaps a bit inappropriate but it's the only way sociolinguists are able to get what they need) and then take a look at that conversation and analyze it. You'll be amazed at what you find. Deborah Tannen is one of my favorite linguists and she now has a new book about how mothers and daughters communicate. "Are you going to dice those tomatoes?", a simple question from mother to daughter can cause the daughter to get really upset because the implications in that question are endless. "What you can't just let me cut up a tomato without judging me?" (mom really wants the tomatoes sliced but oh well)
Beating around the bush gets us all in trouble. I do it with my son sometimes (he's 14 and driving me nuts) and I really should just say "pick up your socks" rather than "are those your socks?" when he knows that I know damn well they are his socks and I really want him to pick them up! It's amazing how seldom we really say what we mean and how much is read "between the lines." This can get us in trouble.
My husband has never said, "Are you going to wear that?" He's figured out that a simple statement of "Gosh you look stunning" will suffice quite well, thank you.