50% of older adults over 60 years old are experiencing social isolation. Assistive technology can provide solutions that promote the connection with their families and other stakeholders. In this context, this paper presents a pilot study of a socialization service with 3 functions tested by 10 older adults and 10 informal caregivers. After a short training, participants were requested to use the system in their daily life for six months. At the beginning (T0) and at the end (T6) of the trial, qualitative structured questionnaires were addressed to investigate training, usability, acceptance (i.e. trust, anxiety, facilitating condition, enjoyment, and attitude), and user experience. Collected results underline good training, good usability of the system (SUS>68), and user experience for both groups. Furthermore, the values associated with acceptance domains are higher than 3.5 for intention to use and trust, at the end of the tests. We can observe a decreasing trend in stress associated with technology use. Informal caregivers have a higher evaluation of the system novelty with respect to older adults. Overall, qualitative feedback collected remarked the good impression of this service among the study's participants. Finally, this study represents a promising starting point for better investigating technology-based services that can improve the quality of life of older people living alone providing them with tools that can decrease their social isolation.Clinical Relevance- The results suggest the potential use of this type of service for promoting socialization among older adults thus reducing their loneliness.