Thick description was originally proposed to overcome the limitations of quantitative research and ground anthropological observations in concrete people’s expectations, rather than in normative theories. The ultimate objective was to account for the emotional aspects of worldviews and value-orientations that would otherwise be left tacit or implicit by quantitative investigations. The present paper aimed at reviewing the _conceptual framework_ that has characterized this relational turn and has made possible a deeper understanding of the subjective experience. The primary objective is thus (...) to make explicit the assumptions upon which thick description relies and discuss how these renewed conditions allow meaning to emerge in interpersonal relationships. We argue that both these objectives would be theoretically attainable if primarily centered on the exploration of the _possibility space_ and on the patient’s experience as driven by the power of _counterfactual thinking_. Under these conditions, human subjects may be led to recognize the contextual and semiotic dimension of _boundaries_ and, in so doing, become aware of the beneficial effects of weaving past and new experiences in meaningful relationships. (shrink)