The aWare Messenger is a family of human aware mobile communication devices targeted toward increasing the comfort of people by mediating rich information about the situation and emotion of other people. It is based on sensing of body physiology, environment, and situation, and it proactively initiates new types of mobile communication and services. We describe our experience in designing and prototyping the first generation of such devices. We are observing that the criteria for engaging in mobile awareness is based on emotional interpretation of context data such as presence, activity, social company, mood, level of busyness, ambient sound, light, and location. These combined metrics decide the topic, tone, and duration of a human interaction. To allow the same rules for engaging in conversations in the mobile world, the aWare Messenger needs to provide similar type of data. We will present the aWare Messenger project - a case study in Human Aware Mobile Computing. We will discuss the social pracices and community [14] issues that led to the development of the concept along with the software and hardware architecture of the aWare Messenger; prototype. Further we will present the physical artifacts design and the considerations for the form, function, user interface modalities, and their practical implications. We will conclude with open research challenges and our future plans.