[Epistemic status: rough heuristics, probably needs refinement, comments are always welcome.]
It has recently occurred to me that, to build close-knit communities, a modified Guess Culture would work better than pure Guess Culture, which is better than Ask Culture.
Guess Culture, at its best, places a heavy emphasis on being considerate. The essence of being considerate is putting effort into building up an accurate mental model of another person, and using that model as a guide to choose actions that would improve the other person's life.
Selfless Dating by Jacob Falkovich is an example of taking thoughtfulness seriously. It doesn't have to apply to dating -- there are many ways to be thoughtful to family, friends, roommates...
Ask Culture, at its best, removes the awkwardness of error correction. When we encounter a situation in territory unfamiliar to our mental map, asking the other person about their preference does not imply that we don't care enough to make a prediction. Similarly, when our mental model of another person makes a prediction error, Ask Culture makes it easier for them to point it out.
My understanding of friendship (which is a foundation of all good interpersonal relationships) is an iterative process of building up more accurate mental models of each other, and using that model to guide decision-making when relevant. For example, if I have told a friend that I'm allergic to X when we go out for food once or twice, I would expect this friend to update their mental of me as "having dietary restrictions." If the next time we go out for food they suggest something that clearly has X in it, I would read that as them having failed to update their mental model of me -- either because they are not good at keeping track of mental models of people, or that they simply don't care about me.
Why is Guess Culture better than Ask Culture in a community context? Compared to Ask Culture, it enables an additional dimension on which to signal -- how accurate my mental model is of you is a reliable signal of how much I care about you. This is an essential signal in a high-trust context.
The downside of pure Guess Culture is that a wrong guess incurs high social cost, since the accuracy of the guesses is a signal of thoughtfulness. The modification here, is to lower the cost for the initial several wrong guesses. Rather than assessing the accuracy of the guesses, this modified version of Guess Culture assesses the rate of improvement of the accuracy.