This paper presents a qualitative investigation on user reactions, opinions, and sentiments about a TV-based technological solution developed within the EasyReach Project of the EU Ambient Assisted Living Joint Program to promote social interaction of less educated elderly people, that is, those individuals who, because of poor scholarization, low income, and, possibly, linguistic barriers, still find it difficult to use computers in order to improve their socialization. Experimental data were collected by extensive trials involving 40 real-end users. A methodology called "scenario engagement" was applied to get participants engaged in a live demonstration with the mediation of a facilitator who assisted elderly people to interact with the system. Results point out that the system can be effectively employed to foster social interaction, particularly when it is introduced in a collective use environment (e.g., Senior Center). Although the focus of the investigation was on information and communication technology-enabled social environments, the end users themselves strongly suggested to include in future system releases extra functions considered as essential opportunities for their potential digital lives: that is, medical or health services and bridges toward public administration.