The paper reports our research aiming at utilization of human interactive communication modeling principles in application to a novel interaction paradigm designed for brain–computer/machine-interfacing (BCI/BMI) technologies as well as for socially aware intelligent environments or communication support systems. Automatic procedures for human affective responses or emotional states estimation are still a hot topic of contemporary research. We propose to utilize human brain and bodily physiological responses for affective/emotional as well as communicative interactivity estimation, which potentially could be used in the future for human–machine/environment interaction design. As a test platform for such an intelligent human–machine communication application, an emotional stimuli paradigm was chosen to evaluate brain responses to various affective stimuli in an emotional empathy mode. Videos with moving faces expressing various emotional displays as well as speech stimuli with similarly emotionally articulated sentences are presented to the subjects in order to further analyze different affective responses. From information processing point of view, several challenges with multimodal signal conditioning and stimuli dynamic response extraction in time frequency domain are addressed. Emotions play an important role in human daily life and human-to-human communication. This is why involvement of affective stimuli principles to human–machine communication or machine-mediated communication with utilization of multichannel neurophysiological and periphery physiological signals monitoring techniques, allowing real-time subjective brain responses evaluation, is discussed. We present our preliminary results and discuss potential applications of brain/body affective responses estimation for future interactive/smart environments.