Contextual privacy is an essential concept in social software communication. Managing privacy of data disclosed in social software dependence strongly on the context the data is disclosed in. The sheer amount of posts and audiences may lead to context ambiguity. Ambiguity can affect contextual privacy management and effective communication. Current contextual privacy management approaches can be either too complex to use, or too simple to offer fine-grained control. In many cases, it is challenging to strike a balance between effective control and ease-of-use. In this article, we analyse contextual privacy by in relation to context and communication. We examine a relevant contextual privacy management framework based on the maintenance of the interpretation of data. We propose an architecture based on the utilisation of intelligent mechanisms. We conceptually analyse the usability aspect of the proposed architecture. We conclude by arguing how our conceptual framework can enhance communication and privacy in private and public spaces.