I've experienced this kind of situation before and I'm only recently realizing that this is the nature of that situation and am starting to unravel it.
There are some good examples of that in this talk:
There's also the theory that some people "metabolize" social communication in specific patterns, and different matches of these patterns create different problems or opportunities. The match-up you mention quite often suggests outward actions, or co-decisions that are made after the co-narrowing of possibilities: "Here are five places we can go today. I like them all. Do me a favor and pick your top three?" Accompanied by logical explanations as needed, this can be a really powerful technique. But yeah, also tough stuff...
Quite often it's absolutely ok to make a subjective guess at a best outcome, move ahead, and trust that the other party will understand, based on your decision logic and your general willingness to be open.