well. as a constructivist linguist I would say, it depends on the implicit message of the utterance. out of the context, taking into account the underlying power structures and the ongoing negotiation of the identities of the subjects involved in the dialog, one should be able to classify the question as some kind of speech act. I would say that the speaker is performing an illocutionary directive speech act (Austin), and the motivation/intention of the speaker can only be elucidated in each concrete case.
out of my experience in most cases the speaker is either requesting an honest answer regarding the chose of clothing or demanding approval/confirmation from the hearer.
first case scenario: the answer depends on how the clothing actually fits to the speaker.
second case scenario: "yes, baby, you are stunning. the (dress/pants/tshirt...) looks great on you!"
As I see it, words should be taken at face value and of course the one speaking should be honest. It's when either the speaker or hearer interjects hidden meanings into what is said that things can spiral out of control quick as all those hidden meanings and double-entendras merely open the door for misinterpretations to get in the way and cause undue drama and even destroy a relationship.
There's a big difference in hearing what someone is saying and assuming what someone is saying.
I couldn't agree more.
but then again the meaning of a sentence will never be just the addition of the meanings of all its words, and what is meaning anyway, right?
so we never just hear what someone is saying, verbal communication is inherently related and constructed around all assumptions and knowledge the speakers and hearers have of the world and of themselves, and forcibly contextualized by the circumstances and conditions of the situation. I guess the key to a fair communication is the willingness to question over and over again all the assumptions and (re)encounter your partner(s) and reinvent yourself and your relationship(s) every time...
AW Education: What should I say when she asks, "do I look good in this?"
If you dont say she look great, you are dead in the water. Same as, do I look fat? No sweetie, you look fab in that. Even if she looks like a truck, you say she looks great. Your chances of sex if you even elaborate are slim to none. A woman can spend a fuckin forthnite getting dressed, and if you dont say she looks great at the first possible try will make you sit there like a dog for hours. A man spends a third of his life working, a third sleeping, and a third of his poor life waiting for his woman. I asked one of my customers today if he was gonna have a good weekend. He pointed at his wife and said probably not. I said, at least have a drink. He said, its hard to have a drink with a gun in your mouth!
Also be careful how she phrases the question. If she says 'Do I look good in this?' then of course, and if you really-really love her than it is a definite and very enthusiastic 'Yes.' But then on the otherhand if she asks 'How does this look on me?' or 'How do I look in this?' then that puts you in the hot seat for a simple but creative answer that will assure her that the clothing she has chosen to wear compliments her very well and that she does indeed look very good to you. Vikingsteve has a good point, the simpler the answer, the better.