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Thinking a bit more about this, in an unhealthy Guess culture, empathy starts to become problematic when fewer and fewer bits are provided until empathy is expected to essentially replace a string of zeros. Eventually, the expectation is not just that you’re supposed to anticipate what another person is thinking and feeling, but you’re required to act on it. You have a responsibility for it, until finally you bear the responsibility for how they think and feel. This evolution occurs when the distinction between people as discrete agents is blurred. Those suffering from borderline personality disorder or narcissistic personality disorder are particularly inclined to erase those distinctions.
Perhaps Guess culture has its origins in the expectation of empathetic engagement? The shirt ironing example suggests as much. Words are sufficient to express ideas, but they don't always efficiently relay all encoded information. To accomplish this - to fill in the missing bits - empathy can be a powerful facilitator. Perhaps the Guess cultures we find toxic are those in which this expectation of empathetic engagement has mutated into an expectation to anticipate and manage others' emotions.