Since our daily life is becoming more and more complex, it is difficult to make a decision for a variety of occurrences in our daily life. Of course, the Internet gives us a possibility to reactively find necessary information through search engines or browsing hyperlinks among Web pages. But, it requires users understand what they like to know and what they should do for finding the currently necessary information. Also, they need great efforts to collect a set of necessary information reactively for making their decisions. It requires us always continue to be rational to think consciously with heavy cognitive load. If users receive necessary information proactively using information technologies, it is helpful to make reasonable decisions without heavy cognition, and their daily lives will become less stressful and more pleasurable due to desirable decision making. We are developing several case studies to support the user's decision making in our daily life by returning necessary information proactively, and the information is embodied into our daily environment to avoid information overload. This paper shows two case studies and analyzes them to make our daily life more desirable. The purpose of the analysis is to understand the current status of proactive ambient social media and to identify a set of future challenges.