Social media services are increasingly used to support social interaction among young people and adults. Older adults however, are often reluctant to use social media services, and prefer to socialize through face-to-face meetings or telephone conversations. Moreover, the time periods that family members have for socializing can be different, as they may have a different schedule for conducting activities and commitments during the day. These differences in media preferences and scheduling times for socializing generate a communication asymmetry that socially isolates older adults and negatively impacts their physical and mental health. Based on the analysis of a dataset from two 21-weeks deployment studies and nine semi-structured interviews, we conducted an in-depth formative study trying to understand the communication asymmetry among older adults and their relatives. The results were used to improve the design and implementation of SocialConnector, a cloud-based application that enables older adults to conduct synchronous and asynchronous social interactions with their relatives. The usability of the new system was evaluated to determine if its services contribute to address the stated communication asymmetry. The obtained results provide evidence that the system can successfully help to alleviate the communication breakdowns led by asymmetries in media and time preferences among family members.