OK, being that no one is saying practical advice I’ll start with a tip I developed.
Always give a leveraged option.
I’ll explain, say you want to know if s/he’s pretty or not. If you say ‘is s/he pretty?’ They will always say ‘of course!’ But if you then add right after your question, ‘or does his or her fun personality stand out more than his or her looks’? They can then answer that without feeling bad.
Another example, if you want to know if she is a warm type of girl. Instead of saying, is she the warmer type? And then getting an obvious ‘of course! she’s so warm’. Throw in right away, or is she normal like most girls? Then if warmth is an important thing for you, you know she doesn’t stand out with that. But the other side doesn’t feel bad saying that because you gave an option that doesn’t put her in a bad light either.
Basically, always offer the flip side, but in a positive way.
Am I being clear? Please tell me if not, I will further clarify.
I found this very helpful and hope you do to.