We developed "Aging and Engaging," a web-based intelligent interface, to improve communication skills among older adults. The interface allows users to practice conversations with a virtual assistant and receive feedback on eye contact, speaking volume, smiling, and valence of speech content. Feedback is generated automatically by analyzing the temporal properties of the conversation using the hidden Markov model. The interface was designed with the assistance of an expert advisory panel that works with geriatric patients, as well as a focus group of 12 older adults. To evaluate its effectiveness, we conducted a study with 25 older adults, each of whom participated in four conversations. Participants' response times to questions, as well as the amount of positive feedback, increased gradually through these interactions, as assessed by human judges. Participants found the feedback useful, easy to interpret, and fairly accurate, and expressed their interest in using the system at home. We plan to enroll subjects with difficulties in social communication; have them use the system over time at home in a randomized, controlled study; and measure any changes in their behavior.