This paper describes the results of a research conducted in the European project Accompany, whose aim is to provide older people with services in a motivating and socially acceptable manner to facilitate independent living at home. The project developed a system consisting of a robotic companion, Care-O-bot, as part of a smart environment. An intensive research was conducted to investigate and experiment with robot behaviours that trigger empathic exchanges between an older person and the robot. The paper is articulated in two parts. The first part illustrates the theory that inspired the development of a context-aware Graphical User Interface (GUI) used to interact with the robot. The GUI integrates an expressive mask allowing perspective ...