Coming off a FB discussion going on right now. It made me recall something my grad school professor once told our class. He was a writer and had many writer friends who would show him their work. In terms of the question they would always ask him: "What do you think?" The point the writing was at was of highest importance. If it was a draft (we're talking novels here) that was early enough in the process to be easily revised, my teacher would tend to give a fair evaluation. However, in many cases he was asked what he thought about a novel after it was already published. In those cases, he always chose to be diplomatic and find warm, positive things to say.
So I'm thinking that if you're going shopping with a friend, not under immense pressure for time or because of a particularly pressure-inducing event (wedding, etc.), you would be giving an honest assessment. But if you went to your friend's house the night before her TV interview (or even worse, after the interview) and she asked you if she looked nice in the outfit she had selected, I would guess you should just say yes! Am I right? Does anyone agree with me here? Any other thoughts?