In this paper we propose a gentle watching over system that considers users' situations and quality/privacy requirements, in ubiquitous information environment. To realize a gentle and safe watching-over, we have to cope with real situation of a watched person. Moreover, social relationships between observers and the watched person should be considered to give adequate privacy level to the services. To do this, we propose a ubiquitous watch-over system "uEyes". In uEyes we introduce a distinguished feature for watching: Social awareness. To realize the feature, environmental information acquired from real world and knowledge on social activities of people are effectively combined. Based on the advanced feature, live video streaming system is dynamically constructed according to the users' situation in runtime. We implemented a prototype of uEyes for watching over elderly people, and performed some experiments based on several scenarios. From the experimental results, we confirmed effectiveness of our proposed system.