The aim of this work is to analyze the Classical theoretical models based on the relationship between stress and well-being with a special focus on some limits of interpretation, concerning short and long term learning processes. Furthermore, this study underlines the possibility that stress and well-being coexist. Classical theories, are based on monodimensional models which set reality along a continuum from stress to well-being. This work suggests that stress and well-being are independent of each other, for this reason a bidimensinal model is argued. Each dimension may be located in a bipolar scale (eustress vs. distress; well-being vs. malaise). Interaction between the two creates a new interpretative map of their relationship Only in exceptional situations interaction between stress and well being may follow ways mentioned in Classical studies. In normal situation the two coexist alternating in time and social space. As suggested in many studies, between stress and well-being there is a low correlation. Bidimensional model gives a theoretical frame to understand this relationship and help to explain events and situation of life as individual, group or organization.