Abstract This paper presents a novel approach to the estimation of user’s affective states in Human-Computer Interaction. Most of the present approaches divide emotions strictly between positive or negative. However, recent discoveries in the fifield of Emotional Intelligence show that emotions should be rather perceived as context-sensitive engagements with the world. This leads to a need to specify whether the emotions conveyed in a conversation are appropriate for a situation they are expressed in. In the proposed method we use a system for affect analysis on textual input to recognize users emotions and a Web mining technique to verify the contextual appropriateness of those emotions. On this basis a conversational agent can choose to either sympathize with the user or help them manage their emotions. Finally, the results of evaluation of the proposed method with two different conversational agents are discussed, and perspectives for further development of the method are proposed.